util/execqueue: add metrics

Expose enough metrics to get a sense of queue depth, use and if it has
stalled.

Updates tailscale/corp#26058

Signed-off-by: Andrew Dunham <andrew@du.nham.ca>
Change-Id: I271ac8d03f3db587a33aca6964fe92f2833e1251

.github/workflows/codeql-analysis.yml

@@ -49,13 +49,13 @@ jobs:
 
     # Install a more recent Go that understands modern go.mod content.
     - name: Install Go
-      uses: actions/setup-go@0a12ed9d6a96ab950c8f026ed9f722fe0da7ef32 # v5.0.2
+      uses: actions/setup-go@3041bf56c941b39c61721a86cd11f3bb1338122a # v5.2.0
       with:
         go-version-file: go.mod
 
     # Initializes the CodeQL tools for scanning.
     - name: Initialize CodeQL
-      uses: github/codeql-action/init@6db8d6351fd0be61f9ed8ebd12ccd35dcec51fea # v3.26.11
+      uses: github/codeql-action/init@b6a472f63d85b9c78a3ac5e89422239fc15e9b3c # v3.28.1
       with:
         languages: ${{ matrix.language }}
         # If you wish to specify custom queries, you can do so here or in a config file.
@@ -66,7 +66,7 @@ jobs:
     # Autobuild attempts to build any compiled languages  (C/C++, C#, or Java).
     # If this step fails, then you should remove it and run the build manually (see below)
     - name: Autobuild
-      uses: github/codeql-action/autobuild@6db8d6351fd0be61f9ed8ebd12ccd35dcec51fea # v3.26.11
+      uses: github/codeql-action/autobuild@b6a472f63d85b9c78a3ac5e89422239fc15e9b3c # v3.28.1
 
     # ℹ️ Command-line programs to run using the OS shell.
     # 📚 https://git.io/JvXDl
@@ -80,4 +80,4 @@ jobs:
     #   make release
 
     - name: Perform CodeQL Analysis
-      uses: github/codeql-action/analyze@6db8d6351fd0be61f9ed8ebd12ccd35dcec51fea # v3.26.11
+      uses: github/codeql-action/analyze@b6a472f63d85b9c78a3ac5e89422239fc15e9b3c # v3.28.1

.github/workflows/golangci-lint.yml

@@ -25,14 +25,13 @@ jobs:
     steps:
       - uses: actions/checkout@692973e3d937129bcbf40652eb9f2f61becf3332 # v4.1.7
 
-      - uses: actions/setup-go@0a12ed9d6a96ab950c8f026ed9f722fe0da7ef32 # v5.0.2
+      - uses: actions/setup-go@3041bf56c941b39c61721a86cd11f3bb1338122a # v5.2.0
         with:
           go-version-file: go.mod
           cache: false
 
       - name: golangci-lint
-        # Note: this is the 'v6.1.0' tag as of 2024-08-21
-        uses: golangci/golangci-lint-action@aaa42aa0628b4ae2578232a66b541047968fac86
+        uses: golangci/golangci-lint-action@ec5d18412c0aeab7936cb16880d708ba2a64e1ae # v6.2.0
         with:
           version: v1.60
 

.github/workflows/govulncheck.yml

@@ -24,13 +24,13 @@ jobs:
 
       - name: Post to slack
         if: failure() && github.event_name == 'schedule'
-        uses: slackapi/slack-github-action@37ebaef184d7626c5f204ab8d3baff4262dd30f0 # v1.27.0
-        env:
-          SLACK_BOT_TOKEN: ${{ secrets.GOVULNCHECK_BOT_TOKEN }}
+        uses: slackapi/slack-github-action@485a9d42d3a73031f12ec201c457e2162c45d02d # v2.0.0
         with:
-          channel-id: 'C05PXRM304B'
+          method: chat.postMessage
+          token: ${{ secrets.GOVULNCHECK_BOT_TOKEN }}
           payload: |
             {
+              "channel": "C05PXRM304B",
               "blocks": [
                 {
                   "type": "section",

.github/workflows/installer.yml

@@ -6,11 +6,13 @@ on:
       - "main"
     paths:
       - scripts/installer.sh
+      - .github/workflows/installer.yml
   pull_request:
     branches:
       - "*"
     paths:
       - scripts/installer.sh
+      - .github/workflows/installer.yml
 
 jobs:
   test:
@@ -29,10 +31,9 @@ jobs:
           - "debian:stable-slim"
           - "debian:testing-slim"
           - "debian:sid-slim"
-          - "ubuntu:18.04"
           - "ubuntu:20.04"
           - "ubuntu:22.04"
-          - "ubuntu:23.04"
+          - "ubuntu:24.04"
           - "elementary/docker:stable"
           - "elementary/docker:unstable"
           - "parrotsec/core:lts-amd64"
@@ -48,7 +49,7 @@ jobs:
           - "opensuse/leap:latest"
           - "opensuse/tumbleweed:latest"
           - "archlinux:latest"
-          - "alpine:3.14"
+          - "alpine:3.21"
           - "alpine:latest"
           - "alpine:edge"
         deps:
@@ -58,10 +59,6 @@ jobs:
           # Check a few images with wget rather than curl.
           - { image: "debian:oldstable-slim", deps: "wget" }
           - { image: "debian:sid-slim", deps: "wget" }
-          - { image: "ubuntu:23.04", deps: "wget" }
-          # Ubuntu 16.04 also needs apt-transport-https installed.
-          - { image: "ubuntu:16.04", deps: "curl apt-transport-https" }
-          - { image: "ubuntu:16.04", deps: "wget apt-transport-https" }
     runs-on: ubuntu-latest
     container:
       image: ${{ matrix.image }}

.github/workflows/test.yml

@@ -80,7 +80,7 @@ jobs:
     - name: checkout
       uses: actions/checkout@692973e3d937129bcbf40652eb9f2f61becf3332 # v4.1.7
     - name: Restore Cache
-      uses: actions/cache@2cdf405574d6ef1f33a1d12acccd3ae82f47b3f2 # v4.1.0
+      uses: actions/cache@1bd1e32a3bdc45362d1e726936510720a7c30a57 # v4.2.0
       with:
         # Note: unlike the other setups, this is only grabbing the mod download
         # cache, rather than the whole mod directory, as the download cache
@@ -153,13 +153,13 @@ jobs:
       uses: actions/checkout@692973e3d937129bcbf40652eb9f2f61becf3332 # v4.1.7
 
     - name: Install Go
-      uses: actions/setup-go@0a12ed9d6a96ab950c8f026ed9f722fe0da7ef32 # v5.0.2
+      uses: actions/setup-go@3041bf56c941b39c61721a86cd11f3bb1338122a # v5.2.0
       with:
         go-version-file: go.mod
         cache: false
 
     - name: Restore Cache
-      uses: actions/cache@2cdf405574d6ef1f33a1d12acccd3ae82f47b3f2 # v4.1.0
+      uses: actions/cache@1bd1e32a3bdc45362d1e726936510720a7c30a57 # v4.2.0
       with:
         # Note: unlike the other setups, this is only grabbing the mod download
         # cache, rather than the whole mod directory, as the download cache
@@ -260,7 +260,7 @@ jobs:
     - name: checkout
       uses: actions/checkout@692973e3d937129bcbf40652eb9f2f61becf3332 # v4.1.7
     - name: Restore Cache
-      uses: actions/cache@2cdf405574d6ef1f33a1d12acccd3ae82f47b3f2 # v4.1.0
+      uses: actions/cache@1bd1e32a3bdc45362d1e726936510720a7c30a57 # v4.2.0
       with:
         # Note: unlike the other setups, this is only grabbing the mod download
         # cache, rather than the whole mod directory, as the download cache
@@ -313,13 +313,19 @@ jobs:
           # AIX
           - goos: aix
             goarch: ppc64
+          # Solaris
+          - goos: solaris
+            goarch: amd64
+          # illumos
+          - goos: illumos
+            goarch: amd64
 
     runs-on: ubuntu-22.04
     steps:
     - name: checkout
       uses: actions/checkout@692973e3d937129bcbf40652eb9f2f61becf3332 # v4.1.7
     - name: Restore Cache
-      uses: actions/cache@2cdf405574d6ef1f33a1d12acccd3ae82f47b3f2 # v4.1.0
+      uses: actions/cache@1bd1e32a3bdc45362d1e726936510720a7c30a57 # v4.2.0
       with:
         # Note: unlike the other setups, this is only grabbing the mod download
         # cache, rather than the whole mod directory, as the download cache
@@ -367,7 +373,7 @@ jobs:
     - name: checkout
       uses: actions/checkout@692973e3d937129bcbf40652eb9f2f61becf3332 # v4.1.7
     - name: Restore Cache
-      uses: actions/cache@2cdf405574d6ef1f33a1d12acccd3ae82f47b3f2 # v4.1.0
+      uses: actions/cache@1bd1e32a3bdc45362d1e726936510720a7c30a57 # v4.2.0
       with:
         # Note: unlike the other setups, this is only grabbing the mod download
         # cache, rather than the whole mod directory, as the download cache
@@ -461,7 +467,7 @@ jobs:
       run: |
         echo "artifacts_path=$(realpath .)" >> $GITHUB_ENV
     - name: upload crash
-      uses: actions/upload-artifact@50769540e7f4bd5e21e526ee35c689e35e0d6874 # v4.4.0
+      uses: actions/upload-artifact@65c4c4a1ddee5b72f698fdd19549f0f0fb45cf08 # v4.6.0
       if: steps.run.outcome != 'success' && steps.build.outcome == 'success'
       with:
         name: artifacts
@@ -563,8 +569,10 @@ jobs:
       # By having the job always run, but skipping its only step as needed, we
       # let the CI output collapse nicely in PRs.
       if: failure() && github.event_name == 'push'
-      uses: slackapi/slack-github-action@37ebaef184d7626c5f204ab8d3baff4262dd30f0 # v1.27.0
+      uses: slackapi/slack-github-action@485a9d42d3a73031f12ec201c457e2162c45d02d # v2.0.0
       with:
+        webhook: ${{ secrets.SLACK_WEBHOOK_URL }}
+        webhook-type: incoming-webhook
         payload: |
           {
             "attachments": [{
@@ -576,9 +584,6 @@ jobs:
               "color": "danger"
             }]
           }
-      env:
-        SLACK_WEBHOOK_URL: ${{ secrets.SLACK_WEBHOOK_URL }}
-        SLACK_WEBHOOK_TYPE: INCOMING_WEBHOOK
 
   check_mergeability:
     if: always()

.github/workflows/update-flake.yml

@@ -36,7 +36,7 @@ jobs:
           private_key: ${{ secrets.LICENSING_APP_PRIVATE_KEY }}
 
       - name: Send pull request
-        uses: peter-evans/create-pull-request@5e914681df9dc83aa4e4905692ca88beb2f9e91f #v7.0.5
+        uses: peter-evans/create-pull-request@67ccf781d68cd99b580ae25a5c18a1cc84ffff1f #v7.0.6
         with:
           token: ${{ steps.generate-token.outputs.token }}
           author: Flakes Updater <noreply+flakes-updater@tailscale.com>

.github/workflows/update-webclient-prebuilt.yml

@@ -35,7 +35,7 @@ jobs:
 
       - name: Send pull request
         id: pull-request
-        uses: peter-evans/create-pull-request@5e914681df9dc83aa4e4905692ca88beb2f9e91f #v7.0.5
+        uses: peter-evans/create-pull-request@67ccf781d68cd99b580ae25a5c18a1cc84ffff1f #v7.0.6
         with:
           token: ${{ steps.generate-token.outputs.token }}
           author: OSS Updater <noreply+oss-updater@tailscale.com>

Makefile

@@ -100,7 +100,7 @@ publishdevoperator: ## Build and publish k8s-operator image to location specifie
 	@test "${REPO}" != "ghcr.io/tailscale/tailscale" || (echo "REPO=... must not be ghcr.io/tailscale/tailscale" && exit 1)
 	@test "${REPO}" != "tailscale/k8s-operator" || (echo "REPO=... must not be tailscale/k8s-operator" && exit 1)
 	@test "${REPO}" != "ghcr.io/tailscale/k8s-operator" || (echo "REPO=... must not be ghcr.io/tailscale/k8s-operator" && exit 1)
-	TAGS="${TAGS}" REPOS=${REPO} PLATFORM=${PLATFORM} PUSH=true TARGET=operator ./build_docker.sh
+	TAGS="${TAGS}" REPOS=${REPO} PLATFORM=${PLATFORM} PUSH=true TARGET=k8s-operator ./build_docker.sh
 
 publishdevnameserver: ## Build and publish k8s-nameserver image to location specified by ${REPO}
 	@test -n "${REPO}" || (echo "REPO=... required; e.g. REPO=ghcr.io/${USER}/tailscale" && exit 1)
@@ -116,7 +116,6 @@ sshintegrationtest: ## Run the SSH integration tests in various Docker container
 	GOOS=linux GOARCH=amd64 ./tool/go build -o ssh/tailssh/testcontainers/tailscaled ./cmd/tailscaled && \
 	echo "Testing on ubuntu:focal" && docker build --build-arg="BASE=ubuntu:focal" -t ssh-ubuntu-focal ssh/tailssh/testcontainers && \
 	echo "Testing on ubuntu:jammy" && docker build --build-arg="BASE=ubuntu:jammy" -t ssh-ubuntu-jammy ssh/tailssh/testcontainers && \
-	echo "Testing on ubuntu:mantic" && docker build --build-arg="BASE=ubuntu:mantic" -t ssh-ubuntu-mantic ssh/tailssh/testcontainers && \
 	echo "Testing on ubuntu:noble" && docker build --build-arg="BASE=ubuntu:noble" -t ssh-ubuntu-noble ssh/tailssh/testcontainers && \
 	echo "Testing on alpine:latest" && docker build --build-arg="BASE=alpine:latest" -t ssh-alpine-latest ssh/tailssh/testcontainers
 

README.md

@@ -72,7 +72,7 @@ Origin](https://en.wikipedia.org/wiki/Developer_Certificate_of_Origin)
 `Signed-off-by` lines in commits.
 
 See `git log` for our commit message style. It's basically the same as
-[Go's style](https://github.com/golang/go/wiki/CommitMessage).
+[Go's style](https://go.dev/wiki/CommitMessage).
 
 ## About Us
 

VERSION.txt

@@ -1 +1 @@
-1.77.0
+1.79.0

appc/appconnector.go

@@ -18,7 +18,6 @@ import (
 	"sync"
 	"time"
 
-	xmaps "golang.org/x/exp/maps"
 	"golang.org/x/net/dns/dnsmessage"
 	"tailscale.com/types/logger"
 	"tailscale.com/types/views"
@@ -291,11 +290,11 @@ func (e *AppConnector) updateDomains(domains []string) {
 			}
 		}
 		if err := e.routeAdvertiser.UnadvertiseRoute(toRemove...); err != nil {
-			e.logf("failed to unadvertise routes on domain removal: %v: %v: %v", xmaps.Keys(oldDomains), toRemove, err)
+			e.logf("failed to unadvertise routes on domain removal: %v: %v: %v", slicesx.MapKeys(oldDomains), toRemove, err)
 		}
 	}
 
-	e.logf("handling domains: %v and wildcards: %v", xmaps.Keys(e.domains), e.wildcards)
+	e.logf("handling domains: %v and wildcards: %v", slicesx.MapKeys(e.domains), e.wildcards)
 }
 
 // updateRoutes merges the supplied routes into the currently configured routes. The routes supplied
@@ -354,7 +353,7 @@ func (e *AppConnector) Domains() views.Slice[string] {
 	e.mu.Lock()
 	defer e.mu.Unlock()
 
-	return views.SliceOf(xmaps.Keys(e.domains))
+	return views.SliceOf(slicesx.MapKeys(e.domains))
 }
 
 // DomainRoutes returns a map of domains to resolved IP
@@ -375,13 +374,13 @@ func (e *AppConnector) DomainRoutes() map[string][]netip.Addr {
 // response is being returned over the PeerAPI. The response is parsed and
 // matched against the configured domains, if matched the routeAdvertiser is
 // advised to advertise the discovered route.
-func (e *AppConnector) ObserveDNSResponse(res []byte) {
+func (e *AppConnector) ObserveDNSResponse(res []byte) error {
 	var p dnsmessage.Parser
 	if _, err := p.Start(res); err != nil {
-		return
+		return err
 	}
 	if err := p.SkipAllQuestions(); err != nil {
-		return
+		return err
 	}
 
 	// cnameChain tracks a chain of CNAMEs for a given query in order to reverse
@@ -400,12 +399,12 @@ func (e *AppConnector) ObserveDNSResponse(res []byte) {
 			break
 		}
 		if err != nil {
-			return
+			return err
 		}
 
 		if h.Class != dnsmessage.ClassINET {
 			if err := p.SkipAnswer(); err != nil {
-				return
+				return err
 			}
 			continue
 		}
@@ -414,7 +413,7 @@ func (e *AppConnector) ObserveDNSResponse(res []byte) {
 		case dnsmessage.TypeCNAME, dnsmessage.TypeA, dnsmessage.TypeAAAA:
 		default:
 			if err := p.SkipAnswer(); err != nil {
-				return
+				return err
 			}
 			continue
 
@@ -428,7 +427,7 @@ func (e *AppConnector) ObserveDNSResponse(res []byte) {
 		if h.Type == dnsmessage.TypeCNAME {
 			res, err := p.CNAMEResource()
 			if err != nil {
-				return
+				return err
 			}
 			cname := strings.TrimSuffix(strings.ToLower(res.CNAME.String()), ".")
 			if len(cname) == 0 {
@@ -442,20 +441,20 @@ func (e *AppConnector) ObserveDNSResponse(res []byte) {
 		case dnsmessage.TypeA:
 			r, err := p.AResource()
 			if err != nil {
-				return
+				return err
 			}
 			addr := netip.AddrFrom4(r.A)
 			mak.Set(&addressRecords, domain, append(addressRecords[domain], addr))
 		case dnsmessage.TypeAAAA:
 			r, err := p.AAAAResource()
 			if err != nil {
-				return
+				return err
 			}
 			addr := netip.AddrFrom16(r.AAAA)
 			mak.Set(&addressRecords, domain, append(addressRecords[domain], addr))
 		default:
 			if err := p.SkipAnswer(); err != nil {
-				return
+				return err
 			}
 			continue
 		}
@@ -486,6 +485,7 @@ func (e *AppConnector) ObserveDNSResponse(res []byte) {
 			e.scheduleAdvertisement(domain, toAdvertise...)
 		}
 	}
+	return nil
 }
 
 // starting from the given domain that resolved to an address, find it, or any

appc/appconnector_test.go

@@ -11,13 +11,13 @@ import (
 	"testing"
 	"time"
 
-	xmaps "golang.org/x/exp/maps"
 	"golang.org/x/net/dns/dnsmessage"
 	"tailscale.com/appc/appctest"
 	"tailscale.com/tstest"
 	"tailscale.com/util/clientmetric"
 	"tailscale.com/util/mak"
 	"tailscale.com/util/must"
+	"tailscale.com/util/slicesx"
 )
 
 func fakeStoreRoutes(*RouteInfo) error { return nil }
@@ -50,7 +50,7 @@ func TestUpdateDomains(t *testing.T) {
 		// domains are explicitly downcased on set.
 		a.UpdateDomains([]string{"UP.EXAMPLE.COM"})
 		a.Wait(ctx)
-		if got, want := xmaps.Keys(a.domains), []string{"up.example.com"}; !slices.Equal(got, want) {
+		if got, want := slicesx.MapKeys(a.domains), []string{"up.example.com"}; !slices.Equal(got, want) {
 			t.Errorf("got %v; want %v", got, want)
 		}
 	}
@@ -69,7 +69,9 @@ func TestUpdateRoutes(t *testing.T) {
 		a.updateDomains([]string{"*.example.com"})
 
 		// This route should be collapsed into the range
-		a.ObserveDNSResponse(dnsResponse("a.example.com.", "192.0.2.1"))
+		if err := a.ObserveDNSResponse(dnsResponse("a.example.com.", "192.0.2.1")); err != nil {
+			t.Errorf("ObserveDNSResponse: %v", err)
+		}
 		a.Wait(ctx)
 
 		if !slices.Equal(rc.Routes(), []netip.Prefix{netip.MustParsePrefix("192.0.2.1/32")}) {
@@ -77,7 +79,9 @@ func TestUpdateRoutes(t *testing.T) {
 		}
 
 		// This route should not be collapsed or removed
-		a.ObserveDNSResponse(dnsResponse("b.example.com.", "192.0.0.1"))
+		if err := a.ObserveDNSResponse(dnsResponse("b.example.com.", "192.0.0.1")); err != nil {
+			t.Errorf("ObserveDNSResponse: %v", err)
+		}
 		a.Wait(ctx)
 
 		routes := []netip.Prefix{netip.MustParsePrefix("192.0.2.0/24"), netip.MustParsePrefix("192.0.0.1/32")}
@@ -130,7 +134,9 @@ func TestDomainRoutes(t *testing.T) {
 			a = NewAppConnector(t.Logf, rc, nil, nil)
 		}
 		a.updateDomains([]string{"example.com"})
-		a.ObserveDNSResponse(dnsResponse("example.com.", "192.0.0.8"))
+		if err := a.ObserveDNSResponse(dnsResponse("example.com.", "192.0.0.8")); err != nil {
+			t.Errorf("ObserveDNSResponse: %v", err)
+		}
 		a.Wait(context.Background())
 
 		want := map[string][]netip.Addr{
@@ -155,7 +161,9 @@ func TestObserveDNSResponse(t *testing.T) {
 		}
 
 		// a has no domains configured, so it should not advertise any routes
-		a.ObserveDNSResponse(dnsResponse("example.com.", "192.0.0.8"))
+		if err := a.ObserveDNSResponse(dnsResponse("example.com.", "192.0.0.8")); err != nil {
+			t.Errorf("ObserveDNSResponse: %v", err)
+		}
 		if got, want := rc.Routes(), ([]netip.Prefix)(nil); !slices.Equal(got, want) {
 			t.Errorf("got %v; want %v", got, want)
 		}
@@ -163,7 +171,9 @@ func TestObserveDNSResponse(t *testing.T) {
 		wantRoutes := []netip.Prefix{netip.MustParsePrefix("192.0.0.8/32")}
 
 		a.updateDomains([]string{"example.com"})
-		a.ObserveDNSResponse(dnsResponse("example.com.", "192.0.0.8"))
+		if err := a.ObserveDNSResponse(dnsResponse("example.com.", "192.0.0.8")); err != nil {
+			t.Errorf("ObserveDNSResponse: %v", err)
+		}
 		a.Wait(ctx)
 		if got, want := rc.Routes(), wantRoutes; !slices.Equal(got, want) {
 			t.Errorf("got %v; want %v", got, want)
@@ -172,7 +182,9 @@ func TestObserveDNSResponse(t *testing.T) {
 		// a CNAME record chain should result in a route being added if the chain
 		// matches a routed domain.
 		a.updateDomains([]string{"www.example.com", "example.com"})
-		a.ObserveDNSResponse(dnsCNAMEResponse("192.0.0.9", "www.example.com.", "chain.example.com.", "example.com."))
+		if err := a.ObserveDNSResponse(dnsCNAMEResponse("192.0.0.9", "www.example.com.", "chain.example.com.", "example.com.")); err != nil {
+			t.Errorf("ObserveDNSResponse: %v", err)
+		}
 		a.Wait(ctx)
 		wantRoutes = append(wantRoutes, netip.MustParsePrefix("192.0.0.9/32"))
 		if got, want := rc.Routes(), wantRoutes; !slices.Equal(got, want) {
@@ -181,7 +193,9 @@ func TestObserveDNSResponse(t *testing.T) {
 
 		// a CNAME record chain should result in a route being added if the chain
 		// even if only found in the middle of the chain
-		a.ObserveDNSResponse(dnsCNAMEResponse("192.0.0.10", "outside.example.org.", "www.example.com.", "example.org."))
+		if err := a.ObserveDNSResponse(dnsCNAMEResponse("192.0.0.10", "outside.example.org.", "www.example.com.", "example.org.")); err != nil {
+			t.Errorf("ObserveDNSResponse: %v", err)
+		}
 		a.Wait(ctx)
 		wantRoutes = append(wantRoutes, netip.MustParsePrefix("192.0.0.10/32"))
 		if got, want := rc.Routes(), wantRoutes; !slices.Equal(got, want) {
@@ -190,14 +204,18 @@ func TestObserveDNSResponse(t *testing.T) {
 
 		wantRoutes = append(wantRoutes, netip.MustParsePrefix("2001:db8::1/128"))
 
-		a.ObserveDNSResponse(dnsResponse("example.com.", "2001:db8::1"))
+		if err := a.ObserveDNSResponse(dnsResponse("example.com.", "2001:db8::1")); err != nil {
+			t.Errorf("ObserveDNSResponse: %v", err)
+		}
 		a.Wait(ctx)
 		if got, want := rc.Routes(), wantRoutes; !slices.Equal(got, want) {
 			t.Errorf("got %v; want %v", got, want)
 		}
 
 		// don't re-advertise routes that have already been advertised
-		a.ObserveDNSResponse(dnsResponse("example.com.", "2001:db8::1"))
+		if err := a.ObserveDNSResponse(dnsResponse("example.com.", "2001:db8::1")); err != nil {
+			t.Errorf("ObserveDNSResponse: %v", err)
+		}
 		a.Wait(ctx)
 		if !slices.Equal(rc.Routes(), wantRoutes) {
 			t.Errorf("rc.Routes(): got %v; want %v", rc.Routes(), wantRoutes)
@@ -207,7 +225,9 @@ func TestObserveDNSResponse(t *testing.T) {
 		pfx := netip.MustParsePrefix("192.0.2.0/24")
 		a.updateRoutes([]netip.Prefix{pfx})
 		wantRoutes = append(wantRoutes, pfx)
-		a.ObserveDNSResponse(dnsResponse("example.com.", "192.0.2.1"))
+		if err := a.ObserveDNSResponse(dnsResponse("example.com.", "192.0.2.1")); err != nil {
+			t.Errorf("ObserveDNSResponse: %v", err)
+		}
 		a.Wait(ctx)
 		if !slices.Equal(rc.Routes(), wantRoutes) {
 			t.Errorf("rc.Routes(): got %v; want %v", rc.Routes(), wantRoutes)
@@ -230,7 +250,9 @@ func TestWildcardDomains(t *testing.T) {
 		}
 
 		a.updateDomains([]string{"*.example.com"})
-		a.ObserveDNSResponse(dnsResponse("foo.example.com.", "192.0.0.8"))
+		if err := a.ObserveDNSResponse(dnsResponse("foo.example.com.", "192.0.0.8")); err != nil {
+			t.Errorf("ObserveDNSResponse: %v", err)
+		}
 		a.Wait(ctx)
 		if got, want := rc.Routes(), []netip.Prefix{netip.MustParsePrefix("192.0.0.8/32")}; !slices.Equal(got, want) {
 			t.Errorf("routes: got %v; want %v", got, want)
@@ -438,10 +460,16 @@ func TestUpdateDomainRouteRemoval(t *testing.T) {
 		// adding domains doesn't immediately cause any routes to be advertised
 		assertRoutes("update domains", []netip.Prefix{}, []netip.Prefix{})
 
-		a.ObserveDNSResponse(dnsResponse("a.example.com.", "1.2.3.1"))
-		a.ObserveDNSResponse(dnsResponse("a.example.com.", "1.2.3.2"))
-		a.ObserveDNSResponse(dnsResponse("b.example.com.", "1.2.3.3"))
-		a.ObserveDNSResponse(dnsResponse("b.example.com.", "1.2.3.4"))
+		for _, res := range [][]byte{
+			dnsResponse("a.example.com.", "1.2.3.1"),
+			dnsResponse("a.example.com.", "1.2.3.2"),
+			dnsResponse("b.example.com.", "1.2.3.3"),
+			dnsResponse("b.example.com.", "1.2.3.4"),
+		} {
+			if err := a.ObserveDNSResponse(res); err != nil {
+				t.Errorf("ObserveDNSResponse: %v", err)
+			}
+		}
 		a.Wait(ctx)
 		// observing dns responses causes routes to be advertised
 		assertRoutes("observed dns", prefixes("1.2.3.1/32", "1.2.3.2/32", "1.2.3.3/32", "1.2.3.4/32"), []netip.Prefix{})
@@ -487,10 +515,16 @@ func TestUpdateWildcardRouteRemoval(t *testing.T) {
 		// adding domains doesn't immediately cause any routes to be advertised
 		assertRoutes("update domains", []netip.Prefix{}, []netip.Prefix{})
 
-		a.ObserveDNSResponse(dnsResponse("a.example.com.", "1.2.3.1"))
-		a.ObserveDNSResponse(dnsResponse("a.example.com.", "1.2.3.2"))
-		a.ObserveDNSResponse(dnsResponse("1.b.example.com.", "1.2.3.3"))
-		a.ObserveDNSResponse(dnsResponse("2.b.example.com.", "1.2.3.4"))
+		for _, res := range [][]byte{
+			dnsResponse("a.example.com.", "1.2.3.1"),
+			dnsResponse("a.example.com.", "1.2.3.2"),
+			dnsResponse("1.b.example.com.", "1.2.3.3"),
+			dnsResponse("2.b.example.com.", "1.2.3.4"),
+		} {
+			if err := a.ObserveDNSResponse(res); err != nil {
+				t.Errorf("ObserveDNSResponse: %v", err)
+			}
+		}
 		a.Wait(ctx)
 		// observing dns responses causes routes to be advertised
 		assertRoutes("observed dns", prefixes("1.2.3.1/32", "1.2.3.2/32", "1.2.3.3/32", "1.2.3.4/32"), []netip.Prefix{})

atomicfile/atomicfile.go

@@ -15,8 +15,9 @@ import (
 )
 
 // WriteFile writes data to filename+some suffix, then renames it into filename.
-// The perm argument is ignored on Windows. If the target filename already
-// exists but is not a regular file, WriteFile returns an error.
+// The perm argument is ignored on Windows, but if the target filename already
+// exists then the target file's attributes and ACLs are preserved. If the target
+// filename already exists but is not a regular file, WriteFile returns an error.
 func WriteFile(filename string, data []byte, perm os.FileMode) (err error) {
 	fi, err := os.Stat(filename)
 	if err == nil && !fi.Mode().IsRegular() {
@@ -47,5 +48,5 @@ func WriteFile(filename string, data []byte, perm os.FileMode) (err error) {
 	if err := f.Close(); err != nil {
 		return err
 	}
-	return os.Rename(tmpName, filename)
+	return rename(tmpName, filename)
 }

atomicfile/atomicfile_notwindows.go

@@ -0,0 +1,14 @@
+// Copyright (c) Tailscale Inc & AUTHORS
+// SPDX-License-Identifier: BSD-3-Clause
+
+//go:build !windows
+
+package atomicfile
+
+import (
+	"os"
+)
+
+func rename(srcFile, destFile string) error {
+	return os.Rename(srcFile, destFile)
+}

atomicfile/atomicfile_windows.go

@@ -0,0 +1,33 @@
+// Copyright (c) Tailscale Inc & AUTHORS
+// SPDX-License-Identifier: BSD-3-Clause
+
+package atomicfile
+
+import (
+	"os"
+
+	"golang.org/x/sys/windows"
+)
+
+func rename(srcFile, destFile string) error {
+	// Use replaceFile when possible to preserve the original file's attributes and ACLs.
+	if err := replaceFile(destFile, srcFile); err == nil || err != windows.ERROR_FILE_NOT_FOUND {
+		return err
+	}
+	// destFile doesn't exist. Just do a normal rename.
+	return os.Rename(srcFile, destFile)
+}
+
+func replaceFile(destFile, srcFile string) error {
+	destFile16, err := windows.UTF16PtrFromString(destFile)
+	if err != nil {
+		return err
+	}
+
+	srcFile16, err := windows.UTF16PtrFromString(srcFile)
+	if err != nil {
+		return err
+	}
+
+	return replaceFileW(destFile16, srcFile16, nil, 0, nil, nil)
+}

atomicfile/atomicfile_windows_test.go

@@ -0,0 +1,146 @@
+// Copyright (c) Tailscale Inc & AUTHORS
+// SPDX-License-Identifier: BSD-3-Clause
+
+package atomicfile
+
+import (
+	"os"
+	"testing"
+	"unsafe"
+
+	"golang.org/x/sys/windows"
+)
+
+var _SECURITY_RESOURCE_MANAGER_AUTHORITY = windows.SidIdentifierAuthority{[6]byte{0, 0, 0, 0, 0, 9}}
+
+// makeRandomSID generates a SID derived from a v4 GUID.
+// This is basically the same algorithm used by browser sandboxes for generating
+// random SIDs.
+func makeRandomSID() (*windows.SID, error) {
+	guid, err := windows.GenerateGUID()
+	if err != nil {
+		return nil, err
+	}
+
+	rids := *((*[4]uint32)(unsafe.Pointer(&guid)))
+
+	var pSID *windows.SID
+	if err := windows.AllocateAndInitializeSid(&_SECURITY_RESOURCE_MANAGER_AUTHORITY, 4, rids[0], rids[1], rids[2], rids[3], 0, 0, 0, 0, &pSID); err != nil {
+		return nil, err
+	}
+	defer windows.FreeSid(pSID)
+
+	// Make a copy that lives on the Go heap
+	return pSID.Copy()
+}
+
+func getExistingFileSD(name string) (*windows.SECURITY_DESCRIPTOR, error) {
+	const infoFlags = windows.DACL_SECURITY_INFORMATION
+	return windows.GetNamedSecurityInfo(name, windows.SE_FILE_OBJECT, infoFlags)
+}
+
+func getExistingFileDACL(name string) (*windows.ACL, error) {
+	sd, err := getExistingFileSD(name)
+	if err != nil {
+		return nil, err
+	}
+
+	dacl, _, err := sd.DACL()
+	return dacl, err
+}
+
+func addDenyACEForRandomSID(dacl *windows.ACL) (*windows.ACL, error) {
+	randomSID, err := makeRandomSID()
+	if err != nil {
+		return nil, err
+	}
+
+	randomSIDTrustee := windows.TRUSTEE{nil, windows.NO_MULTIPLE_TRUSTEE,
+		windows.TRUSTEE_IS_SID, windows.TRUSTEE_IS_UNKNOWN,
+		windows.TrusteeValueFromSID(randomSID)}
+
+	entries := []windows.EXPLICIT_ACCESS{
+		{
+			windows.GENERIC_ALL,
+			windows.DENY_ACCESS,
+			windows.NO_INHERITANCE,
+			randomSIDTrustee,
+		},
+	}
+
+	return windows.ACLFromEntries(entries, dacl)
+}
+
+func setExistingFileDACL(name string, dacl *windows.ACL) error {
+	return windows.SetNamedSecurityInfo(name, windows.SE_FILE_OBJECT,
+		windows.DACL_SECURITY_INFORMATION, nil, nil, dacl, nil)
+}
+
+// makeOrigFileWithCustomDACL creates a new, temporary file with a custom
+// DACL that we can check for later. It returns the name of the temporary
+// file and the security descriptor for the file in SDDL format.
+func makeOrigFileWithCustomDACL() (name, sddl string, err error) {
+	f, err := os.CreateTemp("", "foo*.tmp")
+	if err != nil {
+		return "", "", err
+	}
+	name = f.Name()
+	if err := f.Close(); err != nil {
+		return "", "", err
+	}
+	f = nil
+	defer func() {
+		if err != nil {
+			os.Remove(name)
+		}
+	}()
+
+	dacl, err := getExistingFileDACL(name)
+	if err != nil {
+		return "", "", err
+	}
+
+	// Add a harmless, deny-only ACE for a random SID that isn't used for anything
+	// (but that we can check for later).
+	dacl, err = addDenyACEForRandomSID(dacl)
+	if err != nil {
+		return "", "", err
+	}
+
+	if err := setExistingFileDACL(name, dacl); err != nil {
+		return "", "", err
+	}
+
+	sd, err := getExistingFileSD(name)
+	if err != nil {
+		return "", "", err
+	}
+
+	return name, sd.String(), nil
+}
+
+func TestPreserveSecurityInfo(t *testing.T) {
+	// Make a test file with a custom ACL.
+	origFileName, want, err := makeOrigFileWithCustomDACL()
+	if err != nil {
+		t.Fatalf("makeOrigFileWithCustomDACL returned %v", err)
+	}
+	t.Cleanup(func() {
+		os.Remove(origFileName)
+	})
+
+	if err := WriteFile(origFileName, []byte{}, 0); err != nil {
+		t.Fatalf("WriteFile returned %v", err)
+	}
+
+	// We expect origFileName's security descriptor to be unchanged despite
+	// the WriteFile call.
+	sd, err := getExistingFileSD(origFileName)
+	if err != nil {
+		t.Fatalf("getExistingFileSD(%q) returned %v", origFileName, err)
+	}
+
+	if got := sd.String(); got != want {
+		t.Errorf("security descriptor comparison failed: got %q, want %q", got, want)
+	}
+}

atomicfile/mksyscall.go

@@ -0,0 +1,8 @@
+// Copyright (c) Tailscale Inc & AUTHORS
+// SPDX-License-Identifier: BSD-3-Clause
+
+package atomicfile
+
+//go:generate go run golang.org/x/sys/windows/mkwinsyscall -output zsyscall_windows.go mksyscall.go
+
+//sys replaceFileW(replaced *uint16, replacement *uint16, backup *uint16, flags uint32, exclude unsafe.Pointer, reserved unsafe.Pointer) (err error) [int32(failretval)==0] = kernel32.ReplaceFileW

atomicfile/zsyscall_windows.go

@@ -0,0 +1,52 @@
+// Code generated by 'go generate'; DO NOT EDIT.
+
+package atomicfile
+
+import (
+	"syscall"
+	"unsafe"
+
+	"golang.org/x/sys/windows"
+)
+
+var _ unsafe.Pointer
+
+// Do the interface allocations only once for common
+// Errno values.
+const (
+	errnoERROR_IO_PENDING = 997
+)
+
+var (
+	errERROR_IO_PENDING error = syscall.Errno(errnoERROR_IO_PENDING)
+	errERROR_EINVAL     error = syscall.EINVAL
+)
+
+// errnoErr returns common boxed Errno values, to prevent
+// allocations at runtime.
+func errnoErr(e syscall.Errno) error {
+	switch e {
+	case 0:
+		return errERROR_EINVAL
+	case errnoERROR_IO_PENDING:
+		return errERROR_IO_PENDING
+	}
+	// TODO: add more here, after collecting data on the common
+	// error values see on Windows. (perhaps when running
+	// all.bat?)
+	return e
+}
+
+var (
+	modkernel32 = windows.NewLazySystemDLL("kernel32.dll")
+
+	procReplaceFileW = modkernel32.NewProc("ReplaceFileW")
+)
+
+func replaceFileW(replaced *uint16, replacement *uint16, backup *uint16, flags uint32, exclude unsafe.Pointer, reserved unsafe.Pointer) (err error) {
+	r1, _, e1 := syscall.Syscall6(procReplaceFileW.Addr(), 6, uintptr(unsafe.Pointer(replaced)), uintptr(unsafe.Pointer(replacement)), uintptr(unsafe.Pointer(backup)), uintptr(flags), uintptr(exclude), uintptr(reserved))
+	if int32(r1) == 0 {
+		err = errnoErr(e1)
+	}
+	return
+}

build_dist.sh

@@ -37,7 +37,7 @@ while [ "$#" -gt 1 ]; do
 	--extra-small)
 		shift
 		ldflags="$ldflags -w -s"
-		tags="${tags:+$tags,}ts_omit_aws,ts_omit_bird,ts_omit_tap,ts_omit_kube,ts_omit_completion"
+		tags="${tags:+$tags,}ts_omit_aws,ts_omit_bird,ts_omit_tap,ts_omit_kube,ts_omit_completion,ts_omit_ssh,ts_omit_wakeonlan"
 		;;
 	--box)
 		shift

build_docker.sh

@@ -17,12 +17,20 @@ eval "$(./build_dist.sh shellvars)"
 DEFAULT_TARGET="client"
 DEFAULT_TAGS="v${VERSION_SHORT},v${VERSION_MINOR}"
 DEFAULT_BASE="tailscale/alpine-base:3.18"
+# Set a few pre-defined OCI annotations. The source annotation is used by tools such as Renovate that scan the linked
+# Github repo to find release notes for any new image tags. Note that for official Tailscale images the default
+# annotations defined here will be overriden by release scripts that call this script.
+# https://github.com/opencontainers/image-spec/blob/main/annotations.md#pre-defined-annotation-keys
+DEFAULT_ANNOTATIONS="org.opencontainers.image.source=https://github.com/tailscale/tailscale/blob/main/build_docker.sh,org.opencontainers.image.vendor=Tailscale"
 
 PUSH="${PUSH:-false}"
 TARGET="${TARGET:-${DEFAULT_TARGET}}"
 TAGS="${TAGS:-${DEFAULT_TAGS}}"
 BASE="${BASE:-${DEFAULT_BASE}}"
 PLATFORM="${PLATFORM:-}" # default to all platforms
+# OCI annotations that will be added to the image.
+# https://github.com/opencontainers/image-spec/blob/main/annotations.md
+ANNOTATIONS="${ANNOTATIONS:-${DEFAULT_ANNOTATIONS}}"
 
 case "$TARGET" in
   client)
@@ -43,9 +51,10 @@ case "$TARGET" in
       --repos="${REPOS}" \
       --push="${PUSH}" \
       --target="${PLATFORM}" \
+      --annotations="${ANNOTATIONS}" \
       /usr/local/bin/containerboot
     ;;
-  operator)
+  k8s-operator)
     DEFAULT_REPOS="tailscale/k8s-operator"
     REPOS="${REPOS:-${DEFAULT_REPOS}}"
     go run github.com/tailscale/mkctr \
@@ -60,6 +69,7 @@ case "$TARGET" in
       --repos="${REPOS}" \
       --push="${PUSH}" \
       --target="${PLATFORM}" \
+      --annotations="${ANNOTATIONS}" \
       /usr/local/bin/operator
     ;;
   k8s-nameserver)
@@ -77,6 +87,7 @@ case "$TARGET" in
       --repos="${REPOS}" \
       --push="${PUSH}" \
       --target="${PLATFORM}" \
+      --annotations="${ANNOTATIONS}" \
       /usr/local/bin/k8s-nameserver
     ;;
   *)

client/systray/logo.go

@@ -0,0 +1,319 @@
+// Copyright (c) Tailscale Inc & AUTHORS
+// SPDX-License-Identifier: BSD-3-Clause
+
+//go:build cgo || !darwin
+
+package systray
+
+import (
+	"bytes"
+	"context"
+	"image"
+	"image/color"
+	"image/png"
+	"sync"
+	"time"
+
+	"fyne.io/systray"
+	"github.com/fogleman/gg"
+)
+
+// tsLogo represents the Tailscale logo displayed as the systray icon.
+type tsLogo struct {
+	// dots represents the state of the 3x3 dot grid in the logo.
+	// A 0 represents a gray dot, any other value is a white dot.
+	dots [9]byte
+
+	// dotMask returns an image mask to be used when rendering the logo dots.
+	dotMask func(dc *gg.Context, borderUnits int, radius int) *image.Alpha
+
+	// overlay is called after the dots are rendered to draw an additional overlay.
+	overlay func(dc *gg.Context, borderUnits int, radius int)
+}
+
+var (
+	// disconnected is all gray dots
+	disconnected = tsLogo{dots: [9]byte{
+		0, 0, 0,
+		0, 0, 0,
+		0, 0, 0,
+	}}
+
+	// connected is the normal Tailscale logo
+	connected = tsLogo{dots: [9]byte{
+		0, 0, 0,
+		1, 1, 1,
+		0, 1, 0,
+	}}
+
+	// loading is a special tsLogo value that is not meant to be rendered directly,
+	// but indicates that the loading animation should be shown.
+	loading = tsLogo{dots: [9]byte{'l', 'o', 'a', 'd', 'i', 'n', 'g'}}
+
+	// loadingIcons are shown in sequence as an animated loading icon.
+	loadingLogos = []tsLogo{
+		{dots: [9]byte{
+			0, 1, 1,
+			1, 0, 1,
+			0, 0, 1,
+		}},
+		{dots: [9]byte{
+			0, 1, 1,
+			0, 0, 1,
+			0, 1, 0,
+		}},
+		{dots: [9]byte{
+			0, 1, 1,
+			0, 0, 0,
+			0, 0, 1,
+		}},
+		{dots: [9]byte{
+			0, 0, 1,
+			0, 1, 0,
+			0, 0, 0,
+		}},
+		{dots: [9]byte{
+			0, 1, 0,
+			0, 0, 0,
+			0, 0, 0,
+		}},
+		{dots: [9]byte{
+			0, 0, 0,
+			0, 0, 1,
+			0, 0, 0,
+		}},
+		{dots: [9]byte{
+			0, 0, 0,
+			0, 0, 0,
+			0, 0, 0,
+		}},
+		{dots: [9]byte{
+			0, 0, 1,
+			0, 0, 0,
+			0, 0, 0,
+		}},
+		{dots: [9]byte{
+			0, 0, 0,
+			0, 0, 0,
+			1, 0, 0,
+		}},
+		{dots: [9]byte{
+			0, 0, 0,
+			0, 0, 0,
+			1, 1, 0,
+		}},
+		{dots: [9]byte{
+			0, 0, 0,
+			1, 0, 0,
+			1, 1, 0,
+		}},
+		{dots: [9]byte{
+			0, 0, 0,
+			1, 1, 0,
+			0, 1, 0,
+		}},
+		{dots: [9]byte{
+			0, 0, 0,
+			1, 1, 0,
+			0, 1, 1,
+		}},
+		{dots: [9]byte{
+			0, 0, 0,
+			1, 1, 1,
+			0, 0, 1,
+		}},
+		{dots: [9]byte{
+			0, 1, 0,
+			0, 1, 1,
+			1, 0, 1,
+		}},
+	}
+
+	// exitNodeOnline is the Tailscale logo with an additional arrow overlay in the corner.
+	exitNodeOnline = tsLogo{
+		dots: [9]byte{
+			0, 0, 0,
+			1, 1, 1,
+			0, 1, 0,
+		},
+		// draw an arrow mask in the bottom right corner with a reasonably thick line width.
+		dotMask: func(dc *gg.Context, borderUnits int, radius int) *image.Alpha {
+			bu, r := float64(borderUnits), float64(radius)
+
+			x1 := r * (bu + 3.5)
+			y := r * (bu + 7)
+			x2 := x1 + (r * 5)
+
+			mc := gg.NewContext(dc.Width(), dc.Height())
+			mc.DrawLine(x1, y, x2, y)                 // arrow center line
+			mc.DrawLine(x2-(1.5*r), y-(1.5*r), x2, y) // top of arrow tip
+			mc.DrawLine(x2-(1.5*r), y+(1.5*r), x2, y) // bottom of arrow tip
+			mc.SetLineWidth(r * 3)
+			mc.Stroke()
+			return mc.AsMask()
+		},
+		// draw an arrow in the bottom right corner over the masked area.
+		overlay: func(dc *gg.Context, borderUnits int, radius int) {
+			bu, r := float64(borderUnits), float64(radius)
+
+			x1 := r * (bu + 3.5)
+			y := r * (bu + 7)
+			x2 := x1 + (r * 5)
+
+			dc.DrawLine(x1, y, x2, y)                 // arrow center line
+			dc.DrawLine(x2-(1.5*r), y-(1.5*r), x2, y) // top of arrow tip
+			dc.DrawLine(x2-(1.5*r), y+(1.5*r), x2, y) // bottom of arrow tip
+			dc.SetColor(fg)
+			dc.SetLineWidth(r)
+			dc.Stroke()
+		},
+	}
+
+	// exitNodeOffline is the Tailscale logo with a red "x" in the corner.
+	exitNodeOffline = tsLogo{
+		dots: [9]byte{
+			0, 0, 0,
+			1, 1, 1,
+			0, 1, 0,
+		},
+		// Draw a square that hides the four dots in the bottom right corner,
+		dotMask: func(dc *gg.Context, borderUnits int, radius int) *image.Alpha {
+			bu, r := float64(borderUnits), float64(radius)
+			x := r * (bu + 3)
+
+			mc := gg.NewContext(dc.Width(), dc.Height())
+			mc.DrawRectangle(x, x, r*6, r*6)
+			mc.Fill()
+			return mc.AsMask()
+		},
+		// draw a red "x" over the bottom right corner.
+		overlay: func(dc *gg.Context, borderUnits int, radius int) {
+			bu, r := float64(borderUnits), float64(radius)
+
+			x1 := r * (bu + 4)
+			x2 := x1 + (r * 3.5)
+			dc.DrawLine(x1, x1, x2, x2) // top-left to bottom-right stroke
+			dc.DrawLine(x1, x2, x2, x1) // bottom-left to top-right stroke
+			dc.SetColor(red)
+			dc.SetLineWidth(r)
+			dc.Stroke()
+		},
+	}
+)
+
+var (
+	bg   = color.NRGBA{0, 0, 0, 255}
+	fg   = color.NRGBA{255, 255, 255, 255}
+	gray = color.NRGBA{255, 255, 255, 102}
+	red  = color.NRGBA{229, 111, 74, 255}
+)
+
+// render returns a PNG image of the logo.
+func (logo tsLogo) render() *bytes.Buffer {
+	const borderUnits = 1
+	return logo.renderWithBorder(borderUnits)
+}
+
+// renderWithBorder returns a PNG image of the logo with the specified border width.
+// One border unit is equal to the radius of a tailscale logo dot.
+func (logo tsLogo) renderWithBorder(borderUnits int) *bytes.Buffer {
+	const radius = 25
+	dim := radius * (8 + borderUnits*2)
+
+	dc := gg.NewContext(dim, dim)
+	dc.DrawRectangle(0, 0, float64(dim), float64(dim))
+	dc.SetColor(bg)
+	dc.Fill()
+
+	if logo.dotMask != nil {
+		mask := logo.dotMask(dc, borderUnits, radius)
+		dc.SetMask(mask)
+		dc.InvertMask()
+	}
+
+	for y := 0; y < 3; y++ {
+		for x := 0; x < 3; x++ {
+			px := (borderUnits + 1 + 3*x) * radius
+			py := (borderUnits + 1 + 3*y) * radius
+			col := fg
+			if logo.dots[y*3+x] == 0 {
+				col = gray
+			}
+			dc.DrawCircle(float64(px), float64(py), radius)
+			dc.SetColor(col)
+			dc.Fill()
+		}
+	}
+
+	if logo.overlay != nil {
+		dc.ResetClip()
+		logo.overlay(dc, borderUnits, radius)
+	}
+
+	b := bytes.NewBuffer(nil)
+	png.Encode(b, dc.Image())
+	return b
+}
+
+// setAppIcon renders logo and sets it as the systray icon.
+func setAppIcon(icon tsLogo) {
+	if icon.dots == loading.dots {
+		startLoadingAnimation()
+	} else {
+		stopLoadingAnimation()
+		systray.SetIcon(icon.render().Bytes())
+	}
+}
+
+var (
+	loadingMu sync.Mutex // protects loadingCancel
+
+	// loadingCancel stops the loading animation in the systray icon.
+	// This is nil if the animation is not currently active.
+	loadingCancel func()
+)
+
+// startLoadingAnimation starts the animated loading icon in the system tray.
+// The animation continues until [stopLoadingAnimation] is called.
+// If the loading animation is already active, this func does nothing.
+func startLoadingAnimation() {
+	loadingMu.Lock()
+	defer loadingMu.Unlock()
+
+	if loadingCancel != nil {
+		// loading icon already displayed
+		return
+	}
+
+	ctx := context.Background()
+	ctx, loadingCancel = context.WithCancel(ctx)
+
+	go func() {
+		t := time.NewTicker(500 * time.Millisecond)
+		var i int
+		for {
+			select {
+			case <-ctx.Done():
+				return
+			case <-t.C:
+				systray.SetIcon(loadingLogos[i].render().Bytes())
+				i++
+				if i >= len(loadingLogos) {
+					i = 0
+				}
+			}
+		}
+	}()
+}
+
+// stopLoadingAnimation stops the animated loading icon in the system tray.
+// If the loading animation is not currently active, this func does nothing.
+func stopLoadingAnimation() {
+	loadingMu.Lock()
+	defer loadingMu.Unlock()
+
+	if loadingCancel != nil {
+		loadingCancel()
+		loadingCancel = nil
+	}
+}

client/systray/systray.go

@@ -0,0 +1,712 @@
+// Copyright (c) Tailscale Inc & AUTHORS
+// SPDX-License-Identifier: BSD-3-Clause
+
+//go:build cgo || !darwin
+
+// Package systray provides a minimal Tailscale systray application.
+package systray
+
+import (
+	"context"
+	"errors"
+	"fmt"
+	"io"
+	"log"
+	"net/http"
+	"os"
+	"os/signal"
+	"runtime"
+	"slices"
+	"strings"
+	"sync"
+	"syscall"
+	"time"
+
+	"fyne.io/systray"
+	"github.com/atotto/clipboard"
+	dbus "github.com/godbus/dbus/v5"
+	"github.com/toqueteos/webbrowser"
+	"tailscale.com/client/tailscale"
+	"tailscale.com/ipn"
+	"tailscale.com/ipn/ipnstate"
+	"tailscale.com/tailcfg"
+	"tailscale.com/util/slicesx"
+	"tailscale.com/util/stringsx"
+)
+
+var (
+	// newMenuDelay is the amount of time to sleep after creating a new menu,
+	// but before adding items to it. This works around a bug in some dbus implementations.
+	newMenuDelay time.Duration
+
+	// if true, treat all mullvad exit node countries as single-city.
+	// Instead of rendering a submenu with cities, just select the highest-priority peer.
+	hideMullvadCities bool
+)
+
+// Run starts the systray menu and blocks until the menu exits.
+func (menu *Menu) Run() {
+	menu.updateState()
+
+	// exit cleanly on SIGINT and SIGTERM
+	go func() {
+		interrupt := make(chan os.Signal, 1)
+		signal.Notify(interrupt, syscall.SIGINT, syscall.SIGTERM)
+		select {
+		case <-interrupt:
+			menu.onExit()
+		case <-menu.bgCtx.Done():
+		}
+	}()
+	go menu.lc.IncrementCounter(menu.bgCtx, "systray_start", 1)
+
+	systray.Run(menu.onReady, menu.onExit)
+}
+
+// Menu represents the systray menu, its items, and the current Tailscale state.
+type Menu struct {
+	mu sync.Mutex // protects the entire Menu
+
+	lc          tailscale.LocalClient
+	status      *ipnstate.Status
+	curProfile  ipn.LoginProfile
+	allProfiles []ipn.LoginProfile
+
+	bgCtx    context.Context // ctx for background tasks not involving menu item clicks
+	bgCancel context.CancelFunc
+
+	// Top-level menu items
+	connect    *systray.MenuItem
+	disconnect *systray.MenuItem
+	self       *systray.MenuItem
+	exitNodes  *systray.MenuItem
+	more       *systray.MenuItem
+	quit       *systray.MenuItem
+
+	rebuildCh  chan struct{} // triggers a menu rebuild
+	accountsCh chan ipn.ProfileID
+	exitNodeCh chan tailcfg.StableNodeID // ID of selected exit node
+
+	eventCancel context.CancelFunc // cancel eventLoop
+
+	notificationIcon *os.File // icon used for desktop notifications
+}
+
+func (menu *Menu) init() {
+	if menu.bgCtx != nil {
+		// already initialized
+		return
+	}
+
+	menu.rebuildCh = make(chan struct{}, 1)
+	menu.accountsCh = make(chan ipn.ProfileID)
+	menu.exitNodeCh = make(chan tailcfg.StableNodeID)
+
+	// dbus wants a file path for notification icons, so copy to a temp file.
+	menu.notificationIcon, _ = os.CreateTemp("", "tailscale-systray.png")
+	io.Copy(menu.notificationIcon, connected.renderWithBorder(3))
+
+	menu.bgCtx, menu.bgCancel = context.WithCancel(context.Background())
+	go menu.watchIPNBus()
+}
+
+func init() {
+	if runtime.GOOS != "linux" {
+		// so far, these tweaks are only needed on Linux
+		return
+	}
+
+	desktop := strings.ToLower(os.Getenv("XDG_CURRENT_DESKTOP"))
+	switch desktop {
+	case "gnome":
+		// GNOME expands submenus downward in the main menu, rather than flyouts to the side.
+		// Either as a result of that or another limitation, there seems to be a maximum depth of submenus.
+		// Mullvad countries that have a city submenu are not being rendered, and so can't be selected.
+		// Handle this by simply treating all mullvad countries as single-city and select the best peer.
+		hideMullvadCities = true
+	case "kde":
+		// KDE doesn't need a delay, and actually won't render submenus
+		// if we delay for more than about 400µs.
+		newMenuDelay = 0
+	default:
+		// Add a slight delay to ensure the menu is created before adding items.
+		//
+		// Systray implementations that use libdbusmenu sometimes process messages out of order,
+		// resulting in errors such as:
+		//    (waybar:153009): LIBDBUSMENU-GTK-WARNING **: 18:07:11.551: Children but no menu, someone's been naughty with their 'children-display' property: 'submenu'
+		//
+		// See also: https://github.com/fyne-io/systray/issues/12
+		newMenuDelay = 10 * time.Millisecond
+	}
+}
+
+// onReady is called by the systray package when the menu is ready to be built.
+func (menu *Menu) onReady() {
+	log.Printf("starting")
+	setAppIcon(disconnected)
+	menu.rebuild()
+}
+
+// updateState updates the Menu state from the Tailscale local client.
+func (menu *Menu) updateState() {
+	menu.mu.Lock()
+	defer menu.mu.Unlock()
+	menu.init()
+
+	var err error
+	menu.status, err = menu.lc.Status(menu.bgCtx)
+	if err != nil {
+		log.Print(err)
+	}
+	menu.curProfile, menu.allProfiles, err = menu.lc.ProfileStatus(menu.bgCtx)
+	if err != nil {
+		log.Print(err)
+	}
+}
+
+// rebuild the systray menu based on the current Tailscale state.
+//
+// We currently rebuild the entire menu because it is not easy to update the existing menu.
+// You cannot iterate over the items in a menu, nor can you remove some items like separators.
+// So for now we rebuild the whole thing, and can optimize this later if needed.
+func (menu *Menu) rebuild() {
+	menu.mu.Lock()
+	defer menu.mu.Unlock()
+	menu.init()
+
+	if menu.eventCancel != nil {
+		menu.eventCancel()
+	}
+	ctx := context.Background()
+	ctx, menu.eventCancel = context.WithCancel(ctx)
+
+	systray.ResetMenu()
+
+	menu.connect = systray.AddMenuItem("Connect", "")
+	menu.disconnect = systray.AddMenuItem("Disconnect", "")
+	menu.disconnect.Hide()
+	systray.AddSeparator()
+
+	// delay to prevent race setting icon on first start
+	time.Sleep(newMenuDelay)
+
+	// Set systray menu icon and title.
+	// Also adjust connect/disconnect menu items if needed.
+	var backendState string
+	if menu.status != nil {
+		backendState = menu.status.BackendState
+	}
+	switch backendState {
+	case ipn.Running.String():
+		if menu.status.ExitNodeStatus != nil && !menu.status.ExitNodeStatus.ID.IsZero() {
+			if menu.status.ExitNodeStatus.Online {
+				setTooltip("Using exit node")
+				setAppIcon(exitNodeOnline)
+			} else {
+				setTooltip("Exit node offline")
+				setAppIcon(exitNodeOffline)
+			}
+		} else {
+			setTooltip(fmt.Sprintf("Connected to %s", menu.status.CurrentTailnet.Name))
+			setAppIcon(connected)
+		}
+		menu.connect.SetTitle("Connected")
+		menu.connect.Disable()
+		menu.disconnect.Show()
+		menu.disconnect.Enable()
+	case ipn.Starting.String():
+		setTooltip("Connecting")
+		setAppIcon(loading)
+	default:
+		setTooltip("Disconnected")
+		setAppIcon(disconnected)
+	}
+
+	account := "Account"
+	if pt := profileTitle(menu.curProfile); pt != "" {
+		account = pt
+	}
+	accounts := systray.AddMenuItem(account, "")
+	setRemoteIcon(accounts, menu.curProfile.UserProfile.ProfilePicURL)
+	time.Sleep(newMenuDelay)
+	for _, profile := range menu.allProfiles {
+		title := profileTitle(profile)
+		var item *systray.MenuItem
+		if profile.ID == menu.curProfile.ID {
+			item = accounts.AddSubMenuItemCheckbox(title, "", true)
+		} else {
+			item = accounts.AddSubMenuItem(title, "")
+		}
+		setRemoteIcon(item, profile.UserProfile.ProfilePicURL)
+		onClick(ctx, item, func(ctx context.Context) {
+			select {
+			case <-ctx.Done():
+			case menu.accountsCh <- profile.ID:
+			}
+		})
+	}
+
+	if menu.status != nil && menu.status.Self != nil && len(menu.status.Self.TailscaleIPs) > 0 {
+		title := fmt.Sprintf("This Device: %s (%s)", menu.status.Self.HostName, menu.status.Self.TailscaleIPs[0])
+		menu.self = systray.AddMenuItem(title, "")
+	} else {
+		menu.self = systray.AddMenuItem("This Device: not connected", "")
+		menu.self.Disable()
+	}
+	systray.AddSeparator()
+
+	menu.rebuildExitNodeMenu(ctx)
+
+	if menu.status != nil {
+		menu.more = systray.AddMenuItem("More settings", "")
+		onClick(ctx, menu.more, func(_ context.Context) {
+			webbrowser.Open("http://100.100.100.100/")
+		})
+	}
+
+	menu.quit = systray.AddMenuItem("Quit", "Quit the app")
+	menu.quit.Enable()
+
+	go menu.eventLoop(ctx)
+}
+
+// profileTitle returns the title string for a profile menu item.
+func profileTitle(profile ipn.LoginProfile) string {
+	title := profile.Name
+	if profile.NetworkProfile.DomainName != "" {
+		if runtime.GOOS == "windows" || runtime.GOOS == "darwin" {
+			// windows and mac don't support multi-line menu
+			title += " (" + profile.NetworkProfile.DomainName + ")"
+		} else {
+			title += "\n" + profile.NetworkProfile.DomainName
+		}
+	}
+	return title
+}
+
+var (
+	cacheMu   sync.Mutex
+	httpCache = map[string][]byte{} // URL => response body
+)
+
+// setRemoteIcon sets the icon for menu to the specified remote image.
+// Remote images are fetched as needed and cached.
+func setRemoteIcon(menu *systray.MenuItem, urlStr string) {
+	if menu == nil || urlStr == "" {
+		return
+	}
+
+	cacheMu.Lock()
+	b, ok := httpCache[urlStr]
+	if !ok {
+		resp, err := http.Get(urlStr)
+		if err == nil && resp.StatusCode == http.StatusOK {
+			b, _ = io.ReadAll(resp.Body)
+			httpCache[urlStr] = b
+			resp.Body.Close()
+		}
+	}
+	cacheMu.Unlock()
+
+	if len(b) > 0 {
+		menu.SetIcon(b)
+	}
+}
+
+// setTooltip sets the tooltip text for the systray icon.
+func setTooltip(text string) {
+	if runtime.GOOS == "darwin" || runtime.GOOS == "windows" {
+		systray.SetTooltip(text)
+	} else {
+		// on Linux, SetTitle actually sets the tooltip
+		systray.SetTitle(text)
+	}
+}
+
+// eventLoop is the main event loop for handling click events on menu items
+// and responding to Tailscale state changes.
+// This method does not return until ctx.Done is closed.
+func (menu *Menu) eventLoop(ctx context.Context) {
+	for {
+		select {
+		case <-ctx.Done():
+			return
+		case <-menu.rebuildCh:
+			menu.updateState()
+			menu.rebuild()
+		case <-menu.connect.ClickedCh:
+			_, err := menu.lc.EditPrefs(ctx, &ipn.MaskedPrefs{
+				Prefs: ipn.Prefs{
+					WantRunning: true,
+				},
+				WantRunningSet: true,
+			})
+			if err != nil {
+				log.Printf("error connecting: %v", err)
+			}
+
+		case <-menu.disconnect.ClickedCh:
+			_, err := menu.lc.EditPrefs(ctx, &ipn.MaskedPrefs{
+				Prefs: ipn.Prefs{
+					WantRunning: false,
+				},
+				WantRunningSet: true,
+			})
+			if err != nil {
+				log.Printf("error disconnecting: %v", err)
+			}
+
+		case <-menu.self.ClickedCh:
+			menu.copyTailscaleIP(menu.status.Self)
+
+		case id := <-menu.accountsCh:
+			if err := menu.lc.SwitchProfile(ctx, id); err != nil {
+				log.Printf("error switching to profile ID %v: %v", id, err)
+			}
+
+		case exitNode := <-menu.exitNodeCh:
+			if exitNode.IsZero() {
+				log.Print("disable exit node")
+				if err := menu.lc.SetUseExitNode(ctx, false); err != nil {
+					log.Printf("error disabling exit node: %v", err)
+				}
+			} else {
+				log.Printf("enable exit node: %v", exitNode)
+				mp := &ipn.MaskedPrefs{
+					Prefs: ipn.Prefs{
+						ExitNodeID: exitNode,
+					},
+					ExitNodeIDSet: true,
+				}
+				if _, err := menu.lc.EditPrefs(ctx, mp); err != nil {
+					log.Printf("error setting exit node: %v", err)
+				}
+			}
+
+		case <-menu.quit.ClickedCh:
+			systray.Quit()
+		}
+	}
+}
+
+// onClick registers a click handler for a menu item.
+func onClick(ctx context.Context, item *systray.MenuItem, fn func(ctx context.Context)) {
+	go func() {
+		for {
+			select {
+			case <-ctx.Done():
+				return
+			case <-item.ClickedCh:
+				fn(ctx)
+			}
+		}
+	}()
+}
+
+// watchIPNBus subscribes to the tailscale event bus and sends state updates to chState.
+// This method does not return.
+func (menu *Menu) watchIPNBus() {
+	for {
+		if err := menu.watchIPNBusInner(); err != nil {
+			log.Println(err)
+			if errors.Is(err, context.Canceled) {
+				// If the context got canceled, we will never be able to
+				// reconnect to IPN bus, so exit the process.
+				log.Fatalf("watchIPNBus: %v", err)
+			}
+		}
+		// If our watch connection breaks, wait a bit before reconnecting. No
+		// reason to spam the logs if e.g. tailscaled is restarting or goes
+		// down.
+		time.Sleep(3 * time.Second)
+	}
+}
+
+func (menu *Menu) watchIPNBusInner() error {
+	watcher, err := menu.lc.WatchIPNBus(menu.bgCtx, ipn.NotifyNoPrivateKeys)
+	if err != nil {
+		return fmt.Errorf("watching ipn bus: %w", err)
+	}
+	defer watcher.Close()
+	for {
+		select {
+		case <-menu.bgCtx.Done():
+			return nil
+		default:
+			n, err := watcher.Next()
+			if err != nil {
+				return fmt.Errorf("ipnbus error: %w", err)
+			}
+			var rebuild bool
+			if n.State != nil {
+				log.Printf("new state: %v", n.State)
+				rebuild = true
+			}
+			if n.Prefs != nil {
+				rebuild = true
+			}
+			if rebuild {
+				menu.rebuildCh <- struct{}{}
+			}
+		}
+	}
+}
+
+// copyTailscaleIP copies the first Tailscale IP of the given device to the clipboard
+// and sends a notification with the copied value.
+func (menu *Menu) copyTailscaleIP(device *ipnstate.PeerStatus) {
+	if device == nil || len(device.TailscaleIPs) == 0 {
+		return
+	}
+	name := strings.Split(device.DNSName, ".")[0]
+	ip := device.TailscaleIPs[0].String()
+	err := clipboard.WriteAll(ip)
+	if err != nil {
+		log.Printf("clipboard error: %v", err)
+	}
+
+	menu.sendNotification(fmt.Sprintf("Copied Address for %v", name), ip)
+}
+
+// sendNotification sends a desktop notification with the given title and content.
+func (menu *Menu) sendNotification(title, content string) {
+	conn, err := dbus.SessionBus()
+	if err != nil {
+		log.Printf("dbus: %v", err)
+		return
+	}
+	timeout := 3 * time.Second
+	obj := conn.Object("org.freedesktop.Notifications", "/org/freedesktop/Notifications")
+	call := obj.Call("org.freedesktop.Notifications.Notify", 0, "Tailscale", uint32(0),
+		menu.notificationIcon.Name(), title, content, []string{}, map[string]dbus.Variant{}, int32(timeout.Milliseconds()))
+	if call.Err != nil {
+		log.Printf("dbus: %v", call.Err)
+	}
+}
+
+func (menu *Menu) rebuildExitNodeMenu(ctx context.Context) {
+	if menu.status == nil {
+		return
+	}
+
+	status := menu.status
+	menu.exitNodes = systray.AddMenuItem("Exit Nodes", "")
+	time.Sleep(newMenuDelay)
+
+	// register a click handler for a menu item to set nodeID as the exit node.
+	setExitNodeOnClick := func(item *systray.MenuItem, nodeID tailcfg.StableNodeID) {
+		onClick(ctx, item, func(ctx context.Context) {
+			select {
+			case <-ctx.Done():
+			case menu.exitNodeCh <- nodeID:
+			}
+		})
+	}
+
+	noExitNodeMenu := menu.exitNodes.AddSubMenuItemCheckbox("None", "", status.ExitNodeStatus == nil)
+	setExitNodeOnClick(noExitNodeMenu, "")
+
+	// Show recommended exit node if available.
+	if status.Self.CapMap.Contains(tailcfg.NodeAttrSuggestExitNodeUI) {
+		sugg, err := menu.lc.SuggestExitNode(ctx)
+		if err == nil {
+			title := "Recommended: "
+			if loc := sugg.Location; loc.Valid() && loc.Country() != "" {
+				flag := countryFlag(loc.CountryCode())
+				title += fmt.Sprintf("%s %s: %s", flag, loc.Country(), loc.City())
+			} else {
+				title += strings.Split(sugg.Name, ".")[0]
+			}
+			menu.exitNodes.AddSeparator()
+			rm := menu.exitNodes.AddSubMenuItemCheckbox(title, "", false)
+			setExitNodeOnClick(rm, sugg.ID)
+			if status.ExitNodeStatus != nil && sugg.ID == status.ExitNodeStatus.ID {
+				rm.Check()
+			}
+		}
+	}
+
+	// Add tailnet exit nodes if present.
+	var tailnetExitNodes []*ipnstate.PeerStatus
+	for _, ps := range status.Peer {
+		if ps.ExitNodeOption && ps.Location == nil {
+			tailnetExitNodes = append(tailnetExitNodes, ps)
+		}
+	}
+	if len(tailnetExitNodes) > 0 {
+		menu.exitNodes.AddSeparator()
+		menu.exitNodes.AddSubMenuItem("Tailnet Exit Nodes", "").Disable()
+		for _, ps := range status.Peer {
+			if !ps.ExitNodeOption || ps.Location != nil {
+				continue
+			}
+			name := strings.Split(ps.DNSName, ".")[0]
+			if !ps.Online {
+				name += " (offline)"
+			}
+			sm := menu.exitNodes.AddSubMenuItemCheckbox(name, "", false)
+			if !ps.Online {
+				sm.Disable()
+			}
+			if status.ExitNodeStatus != nil && ps.ID == status.ExitNodeStatus.ID {
+				sm.Check()
+			}
+			setExitNodeOnClick(sm, ps.ID)
+		}
+	}
+
+	// Add mullvad exit nodes if present.
+	var mullvadExitNodes mullvadPeers
+	if status.Self.CapMap.Contains("mullvad") {
+		mullvadExitNodes = newMullvadPeers(status)
+	}
+	if len(mullvadExitNodes.countries) > 0 {
+		menu.exitNodes.AddSeparator()
+		menu.exitNodes.AddSubMenuItem("Location-based Exit Nodes", "").Disable()
+		mullvadMenu := menu.exitNodes.AddSubMenuItemCheckbox("Mullvad VPN", "", false)
+
+		for _, country := range mullvadExitNodes.sortedCountries() {
+			flag := countryFlag(country.code)
+			countryMenu := mullvadMenu.AddSubMenuItemCheckbox(flag+" "+country.name, "", false)
+
+			// single-city country, no submenu
+			if len(country.cities) == 1 || hideMullvadCities {
+				setExitNodeOnClick(countryMenu, country.best.ID)
+				if status.ExitNodeStatus != nil {
+					for _, city := range country.cities {
+						for _, ps := range city.peers {
+							if status.ExitNodeStatus.ID == ps.ID {
+								mullvadMenu.Check()
+								countryMenu.Check()
+							}
+						}
+					}
+				}
+				continue
+			}
+
+			// multi-city country, build submenu with "best available" option and cities.
+			time.Sleep(newMenuDelay)
+			bm := countryMenu.AddSubMenuItemCheckbox("Best Available", "", false)
+			setExitNodeOnClick(bm, country.best.ID)
+			countryMenu.AddSeparator()
+
+			for _, city := range country.sortedCities() {
+				cityMenu := countryMenu.AddSubMenuItemCheckbox(city.name, "", false)
+				setExitNodeOnClick(cityMenu, city.best.ID)
+				if status.ExitNodeStatus != nil {
+					for _, ps := range city.peers {
+						if status.ExitNodeStatus.ID == ps.ID {
+							mullvadMenu.Check()
+							countryMenu.Check()
+							cityMenu.Check()
+						}
+					}
+				}
+			}
+		}
+	}
+
+	// TODO: "Allow Local Network Access" and "Run Exit Node" menu items
+}
+
+// mullvadPeers contains all mullvad peer nodes, sorted by country and city.
+type mullvadPeers struct {
+	countries map[string]*mvCountry // country code (uppercase) => country
+}
+
+// sortedCountries returns countries containing mullvad nodes, sorted by name.
+func (mp mullvadPeers) sortedCountries() []*mvCountry {
+	countries := slicesx.MapValues(mp.countries)
+	slices.SortFunc(countries, func(a, b *mvCountry) int {
+		return stringsx.CompareFold(a.name, b.name)
+	})
+	return countries
+}
+
+type mvCountry struct {
+	code   string
+	name   string
+	best   *ipnstate.PeerStatus // highest priority peer in the country
+	cities map[string]*mvCity   // city code => city
+}
+
+// sortedCities returns cities containing mullvad nodes, sorted by name.
+func (mc *mvCountry) sortedCities() []*mvCity {
+	cities := slicesx.MapValues(mc.cities)
+	slices.SortFunc(cities, func(a, b *mvCity) int {
+		return stringsx.CompareFold(a.name, b.name)
+	})
+	return cities
+}
+
+// countryFlag takes a 2-character ASCII string and returns the corresponding emoji flag.
+// It returns the empty string on error.
+func countryFlag(code string) string {
+	if len(code) != 2 {
+		return ""
+	}
+	runes := make([]rune, 0, 2)
+	for i := range 2 {
+		b := code[i] | 32 // lowercase
+		if b < 'a' || b > 'z' {
+			return ""
+		}
+		// https://en.wikipedia.org/wiki/Regional_indicator_symbol
+		runes = append(runes, 0x1F1E6+rune(b-'a'))
+	}
+	return string(runes)
+}
+
+type mvCity struct {
+	name  string
+	best  *ipnstate.PeerStatus // highest priority peer in the city
+	peers []*ipnstate.PeerStatus
+}
+
+func newMullvadPeers(status *ipnstate.Status) mullvadPeers {
+	countries := make(map[string]*mvCountry)
+	for _, ps := range status.Peer {
+		if !ps.ExitNodeOption || ps.Location == nil {
+			continue
+		}
+		loc := ps.Location
+		country, ok := countries[loc.CountryCode]
+		if !ok {
+			country = &mvCountry{
+				code:   loc.CountryCode,
+				name:   loc.Country,
+				cities: make(map[string]*mvCity),
+			}
+			countries[loc.CountryCode] = country
+		}
+		city, ok := countries[loc.CountryCode].cities[loc.CityCode]
+		if !ok {
+			city = &mvCity{
+				name: loc.City,
+			}
+			countries[loc.CountryCode].cities[loc.CityCode] = city
+		}
+		city.peers = append(city.peers, ps)
+		if city.best == nil || ps.Location.Priority > city.best.Location.Priority {
+			city.best = ps
+		}
+		if country.best == nil || ps.Location.Priority > country.best.Location.Priority {
+			country.best = ps
+		}
+	}
+	return mullvadPeers{countries}
+}
+
+// onExit is called by the systray package when the menu is exiting.
+func (menu *Menu) onExit() {
+	log.Printf("exiting")
+	if menu.bgCancel != nil {
+		menu.bgCancel()
+	}
+	if menu.eventCancel != nil {
+		menu.eventCancel()
+	}
+
+	os.Remove(menu.notificationIcon.Name())
+}

client/tailscale/localclient.go

@@ -1,7 +1,7 @@
 // Copyright (c) Tailscale Inc & AUTHORS
 // SPDX-License-Identifier: BSD-3-Clause
 
-//go:build go1.19
+//go:build go1.22
 
 package tailscale
 
@@ -62,6 +62,12 @@ type LocalClient struct {
 	// machine's tailscaled or equivalent. If nil, a default is used.
 	Dial func(ctx context.Context, network, addr string) (net.Conn, error)
 
+	// Transport optionally specifies an alternate [http.RoundTripper]
+	// used to execute HTTP requests. If nil, a default [http.Transport] is used,
+	// potentially with custom dialing logic from [Dial].
+	// It is primarily used for testing.
+	Transport http.RoundTripper
+
 	// Socket specifies an alternate path to the local Tailscale socket.
 	// If empty, a platform-specific default is used.
 	Socket string
@@ -129,9 +135,9 @@ func (lc *LocalClient) DoLocalRequest(req *http.Request) (*http.Response, error)
 	req.Header.Set("Tailscale-Cap", strconv.Itoa(int(tailcfg.CurrentCapabilityVersion)))
 	lc.tsClientOnce.Do(func() {
 		lc.tsClient = &http.Client{
-			Transport: &http.Transport{
-				DialContext: lc.dialer(),
-			},
+			Transport: cmp.Or(lc.Transport, http.RoundTripper(
+				&http.Transport{DialContext: lc.dialer()}),
+			),
 		}
 	})
 	if !lc.OmitAuth {
@@ -493,6 +499,17 @@ func (lc *LocalClient) DebugAction(ctx context.Context, action string) error {
 	return nil
 }
 
+// DebugActionBody invokes a debug action with a body parameter, such as
+// "debug-force-prefer-derp".
+// These are development tools and subject to change or removal over time.
+func (lc *LocalClient) DebugActionBody(ctx context.Context, action string, rbody io.Reader) error {
+	body, err := lc.send(ctx, "POST", "/localapi/v0/debug?action="+url.QueryEscape(action), 200, rbody)
+	if err != nil {
+		return fmt.Errorf("error %w: %s", err, body)
+	}
+	return nil
+}
+
 // DebugResultJSON invokes a debug action and returns its result as something JSON-able.
 // These are development tools and subject to change or removal over time.
 func (lc *LocalClient) DebugResultJSON(ctx context.Context, action string) (any, error) {
@@ -1327,6 +1344,17 @@ func (lc *LocalClient) SetServeConfig(ctx context.Context, config *ipn.ServeConf
 	return nil
 }
 
+// DisconnectControl shuts down all connections to control, thus making control consider this node inactive. This can be
+// run on HA subnet router or app connector replicas before shutting them down to ensure peers get told to switch over
+// to another replica whilst there is still some grace period for the existing connections to terminate.
+func (lc *LocalClient) DisconnectControl(ctx context.Context) error {
+	_, _, err := lc.sendWithHeaders(ctx, "POST", "/localapi/v0/disconnect-control", 200, nil, nil)
+	if err != nil {
+		return fmt.Errorf("error disconnecting control: %w", err)
+	}
+	return nil
+}
+
 // NetworkLockDisable shuts down network-lock across the tailnet.
 func (lc *LocalClient) NetworkLockDisable(ctx context.Context, secret []byte) error {
 	if _, err := lc.send(ctx, "POST", "/localapi/v0/tka/disable", 200, bytes.NewReader(secret)); err != nil {

client/web/web.go

@@ -89,8 +89,8 @@ type Server struct {
 type ServerMode string
 
 const (
-	// LoginServerMode serves a readonly login client for logging a
-	// node into a tailnet, and viewing a readonly interface of the
+	// LoginServerMode serves a read-only login client for logging a
+	// node into a tailnet, and viewing a read-only interface of the
 	// node's current Tailscale settings.
 	//
 	// In this mode, API calls are authenticated via platform auth.
@@ -110,7 +110,7 @@ const (
 	// This mode restricts the app to only being assessible over Tailscale,
 	// and API calls are authenticated via browser sessions associated with
 	// the source's Tailscale identity. If the source browser does not have
-	// a valid session, a readonly version of the app is displayed.
+	// a valid session, a read-only version of the app is displayed.
 	ManageServerMode ServerMode = "manage"
 )
 
@@ -695,16 +695,16 @@ func (s *Server) serveAPIAuth(w http.ResponseWriter, r *http.Request) {
 	switch {
 	case sErr != nil && errors.Is(sErr, errNotUsingTailscale):
 		s.lc.IncrementCounter(r.Context(), "web_client_viewing_local", 1)
-		resp.Authorized = false // restricted to the readonly view
+		resp.Authorized = false // restricted to the read-only view
 	case sErr != nil && errors.Is(sErr, errNotOwner):
 		s.lc.IncrementCounter(r.Context(), "web_client_viewing_not_owner", 1)
-		resp.Authorized = false // restricted to the readonly view
+		resp.Authorized = false // restricted to the read-only view
 	case sErr != nil && errors.Is(sErr, errTaggedLocalSource):
 		s.lc.IncrementCounter(r.Context(), "web_client_viewing_local_tag", 1)
-		resp.Authorized = false // restricted to the readonly view
+		resp.Authorized = false // restricted to the read-only view
 	case sErr != nil && errors.Is(sErr, errTaggedRemoteSource):
 		s.lc.IncrementCounter(r.Context(), "web_client_viewing_remote_tag", 1)
-		resp.Authorized = false // restricted to the readonly view
+		resp.Authorized = false // restricted to the read-only view
 	case sErr != nil && !errors.Is(sErr, errNoSession):
 		// Any other error.
 		http.Error(w, sErr.Error(), http.StatusInternalServerError)
@@ -804,8 +804,8 @@ type nodeData struct {
 	DeviceName  string
 	TailnetName string // TLS cert name
 	DomainName  string
-	IPv4        string
-	IPv6        string
+	IPv4        netip.Addr
+	IPv6        netip.Addr
 	OS          string
 	IPNVersion  string
 
@@ -864,10 +864,14 @@ func (s *Server) serveGetNodeData(w http.ResponseWriter, r *http.Request) {
 		return
 	}
 	filterRules, _ := s.lc.DebugPacketFilterRules(r.Context())
+	ipv4, ipv6 := s.selfNodeAddresses(r, st)
+
 	data := &nodeData{
 		ID:               st.Self.ID,
 		Status:           st.BackendState,
 		DeviceName:       strings.Split(st.Self.DNSName, ".")[0],
+		IPv4:             ipv4,
+		IPv6:             ipv6,
 		OS:               st.Self.OS,
 		IPNVersion:       strings.Split(st.Version, "-")[0],
 		Profile:          st.User[st.Self.UserID],
@@ -887,10 +891,6 @@ func (s *Server) serveGetNodeData(w http.ResponseWriter, r *http.Request) {
 		ACLAllowsAnyIncomingTraffic: s.aclsAllowAccess(filterRules),
 	}
 
-	ipv4, ipv6 := s.selfNodeAddresses(r, st)
-	data.IPv4 = ipv4.String()
-	data.IPv6 = ipv6.String()
-
 	if hostinfo.GetEnvType() == hostinfo.HomeAssistantAddOn && data.URLPrefix == "" {
 		// X-Ingress-Path is the path prefix in use for Home Assistant
 		// https://developers.home-assistant.io/docs/add-ons/presentation#ingress

cmd/addlicense/main.go

@@ -18,12 +18,12 @@ var (
 )
 
 func usage() {
-	fmt.Fprintf(os.Stderr, `
+	fmt.Fprint(os.Stderr, `
 usage: addlicense -file FILE <subcommand args...>
 `[1:])
 
 	flag.PrintDefaults()
-	fmt.Fprintf(os.Stderr, `
+	fmt.Fprint(os.Stderr, `
 addlicense adds a Tailscale license to the beginning of file.
 
 It is intended for use with 'go generate', so it also runs a subcommand,

cmd/checkmetrics/checkmetrics.go

@@ -0,0 +1,131 @@
+// Copyright (c) Tailscale Inc & AUTHORS
+// SPDX-License-Identifier: BSD-3-Clause
+
+// checkmetrics validates that all metrics in the tailscale client-metrics
+// are documented in a given path or URL.
+package main
+
+import (
+	"context"
+	"flag"
+	"fmt"
+	"io"
+	"log"
+	"net/http"
+	"net/http/httptest"
+	"os"
+	"strings"
+	"time"
+
+	"tailscale.com/ipn/store/mem"
+	"tailscale.com/tsnet"
+	"tailscale.com/tstest/integration/testcontrol"
+	"tailscale.com/util/httpm"
+)
+
+var (
+	kbPath = flag.String("kb-path", "", "filepath to the client-metrics knowledge base")
+	kbUrl  = flag.String("kb-url", "", "URL to the client-metrics knowledge base page")
+)
+
+func main() {
+	flag.Parse()
+	if *kbPath == "" && *kbUrl == "" {
+		log.Fatalf("either -kb-path or -kb-url must be set")
+	}
+
+	var control testcontrol.Server
+	ts := httptest.NewServer(&control)
+	defer ts.Close()
+
+	td, err := os.MkdirTemp("", "testcontrol")
+	if err != nil {
+		log.Fatal(err)
+	}
+	defer os.RemoveAll(td)
+
+	// tsnet is used not used as a Tailscale client, but as a way to
+	// boot up Tailscale, have all the metrics registered, and then
+	// verifiy that all the metrics are documented.
+	tsn := &tsnet.Server{
+		Dir:        td,
+		Store:      new(mem.Store),
+		UserLogf:   log.Printf,
+		Ephemeral:  true,
+		ControlURL: ts.URL,
+	}
+	if err := tsn.Start(); err != nil {
+		log.Fatal(err)
+	}
+	defer tsn.Close()
+
+	log.Printf("checking that all metrics are documented, looking for: %s", tsn.Sys().UserMetricsRegistry().MetricNames())
+
+	if *kbPath != "" {
+		kb, err := readKB(*kbPath)
+		if err != nil {
+			log.Fatalf("reading kb: %v", err)
+		}
+		missing := undocumentedMetrics(kb, tsn.Sys().UserMetricsRegistry().MetricNames())
+
+		if len(missing) > 0 {
+			log.Fatalf("found undocumented metrics in %q: %v", *kbPath, missing)
+		}
+	}
+
+	if *kbUrl != "" {
+		ctx, cancel := context.WithTimeout(context.Background(), 30*time.Second)
+		defer cancel()
+
+		kb, err := getKB(ctx, *kbUrl)
+		if err != nil {
+			log.Fatalf("getting kb: %v", err)
+		}
+		missing := undocumentedMetrics(kb, tsn.Sys().UserMetricsRegistry().MetricNames())
+
+		if len(missing) > 0 {
+			log.Fatalf("found undocumented metrics in %q: %v", *kbUrl, missing)
+		}
+	}
+}
+
+func readKB(path string) (string, error) {
+	b, err := os.ReadFile(path)
+	if err != nil {
+		return "", fmt.Errorf("reading file: %w", err)
+	}
+
+	return string(b), nil
+}
+
+func getKB(ctx context.Context, url string) (string, error) {
+	req, err := http.NewRequestWithContext(ctx, httpm.GET, url, nil)
+	if err != nil {
+		return "", fmt.Errorf("creating request: %w", err)
+	}
+
+	resp, err := http.DefaultClient.Do(req)
+	if err != nil {
+		return "", fmt.Errorf("getting kb page: %w", err)
+	}
+
+	if resp.StatusCode != http.StatusOK {
+		return "", fmt.Errorf("unexpected status code: %d", resp.StatusCode)
+	}
+
+	b, err := io.ReadAll(resp.Body)
+	if err != nil {
+		return "", fmt.Errorf("reading body: %w", err)
+	}
+	return string(b), nil
+}
+
+func undocumentedMetrics(b string, metrics []string) []string {
+	var missing []string
+	for _, metric := range metrics {
+		if !strings.Contains(b, metric) {
+			missing = append(missing, metric)
+		}
+	}
+	return missing
+}

cmd/containerboot/healthz.go

@@ -7,7 +7,6 @@ package main
 
 import (
 	"log"
-	"net"
 	"net/http"
 	"sync"
 )
@@ -23,29 +22,29 @@ type healthz struct {
 func (h *healthz) ServeHTTP(w http.ResponseWriter, r *http.Request) {
 	h.Lock()
 	defer h.Unlock()
+
 	if h.hasAddrs {
 		w.Write([]byte("ok"))
 	} else {
-		http.Error(w, "node currently has no tailscale IPs", http.StatusInternalServerError)
+		http.Error(w, "node currently has no tailscale IPs", http.StatusServiceUnavailable)
 	}
 }
 
-// runHealthz runs a simple HTTP health endpoint on /healthz, listening on the
-// provided address. A containerized tailscale instance is considered healthy if
+func (h *healthz) update(healthy bool) {
+	h.Lock()
+	defer h.Unlock()
+
+	if h.hasAddrs != healthy {
+		log.Println("Setting healthy", healthy)
+	}
+	h.hasAddrs = healthy
+}
+
+// healthHandlers registers a simple health handler at /healthz.
+// A containerized tailscale instance is considered healthy if
 // it has at least one tailnet IP address.
-func runHealthz(addr string, h *healthz) {
-	lis, err := net.Listen("tcp", addr)
-	if err != nil {
-		log.Fatalf("error listening on the provided health endpoint address %q: %v", addr, err)
-	}
-	mux := http.NewServeMux()
-	mux.Handle("/healthz", h)
-	log.Printf("Running healthcheck endpoint at %s/healthz", addr)
-	hs := &http.Server{Handler: mux}
-
-	go func() {
-		if err := hs.Serve(lis); err != nil {
-			log.Fatalf("failed running health endpoint: %v", err)
-		}
-	}()
+func healthHandlers(mux *http.ServeMux) *healthz {
+	h := &healthz{}
+	mux.Handle("GET /healthz", h)
+	return h
 }

cmd/containerboot/kube.go

@@ -9,30 +9,56 @@ import (
 	"context"
 	"encoding/json"
 	"fmt"
-	"log"
 	"net/http"
 	"net/netip"
 	"os"
 
 	"tailscale.com/kube/kubeapi"
 	"tailscale.com/kube/kubeclient"
+	"tailscale.com/kube/kubetypes"
 	"tailscale.com/tailcfg"
 )
 
-// storeDeviceID writes deviceID to 'device_id' data field of the named
-// Kubernetes Secret.
-func storeDeviceID(ctx context.Context, secretName string, deviceID tailcfg.StableNodeID) error {
-	s := &kubeapi.Secret{
-		Data: map[string][]byte{
-			"device_id": []byte(deviceID),
-		},
-	}
-	return kc.StrategicMergePatchSecret(ctx, secretName, s, "tailscale-container")
+// kubeClient is a wrapper around Tailscale's internal kube client that knows how to talk to the kube API server. We use
+// this rather than any of the upstream Kubernetes client libaries to avoid extra imports.
+type kubeClient struct {
+	kubeclient.Client
+	stateSecret string
+	canPatch    bool // whether the client has permissions to patch Kubernetes Secrets
 }
 
-// storeDeviceEndpoints writes device's tailnet IPs and MagicDNS name to fields
-// 'device_ips', 'device_fqdn' of the named Kubernetes Secret.
-func storeDeviceEndpoints(ctx context.Context, secretName string, fqdn string, addresses []netip.Prefix) error {
+func newKubeClient(root string, stateSecret string) (*kubeClient, error) {
+	if root != "/" {
+		// If we are running in a test, we need to set the root path to the fake
+		// service account directory.
+		kubeclient.SetRootPathForTesting(root)
+	}
+	var err error
+	kc, err := kubeclient.New("tailscale-container")
+	if err != nil {
+		return nil, fmt.Errorf("Error creating kube client: %w", err)
+	}
+	if (root != "/") || os.Getenv("TS_KUBERNETES_READ_API_SERVER_ADDRESS_FROM_ENV") == "true" {
+		// Derive the API server address from the environment variables
+		// Used to set http server in tests, or optionally enabled by flag
+		kc.SetURL(fmt.Sprintf("https://%s:%s", os.Getenv("KUBERNETES_SERVICE_HOST"), os.Getenv("KUBERNETES_SERVICE_PORT_HTTPS")))
+	}
+	return &kubeClient{Client: kc, stateSecret: stateSecret}, nil
+}
+
+// storeDeviceID writes deviceID to 'device_id' data field of the client's state Secret.
+func (kc *kubeClient) storeDeviceID(ctx context.Context, deviceID tailcfg.StableNodeID) error {
+	s := &kubeapi.Secret{
+		Data: map[string][]byte{
+			kubetypes.KeyDeviceID: []byte(deviceID),
+		},
+	}
+	return kc.StrategicMergePatchSecret(ctx, kc.stateSecret, s, "tailscale-container")
+}
+
+// storeDeviceEndpoints writes device's tailnet IPs and MagicDNS name to fields 'device_ips', 'device_fqdn' of client's
+// state Secret.
+func (kc *kubeClient) storeDeviceEndpoints(ctx context.Context, fqdn string, addresses []netip.Prefix) error {
 	var ips []string
 	for _, addr := range addresses {
 		ips = append(ips, addr.Addr().String())
@@ -44,16 +70,28 @@ func storeDeviceEndpoints(ctx context.Context, secretName string, fqdn string, a
 
 	s := &kubeapi.Secret{
 		Data: map[string][]byte{
-			"device_fqdn": []byte(fqdn),
-			"device_ips":  deviceIPs,
+			kubetypes.KeyDeviceFQDN: []byte(fqdn),
+			kubetypes.KeyDeviceIPs:  deviceIPs,
 		},
 	}
-	return kc.StrategicMergePatchSecret(ctx, secretName, s, "tailscale-container")
+	return kc.StrategicMergePatchSecret(ctx, kc.stateSecret, s, "tailscale-container")
+}
+
+// storeHTTPSEndpoint writes an HTTPS endpoint exposed by this device via 'tailscale serve' to the client's state
+// Secret. In practice this will be the same value that gets written to 'device_fqdn', but this should only be called
+// when the serve config has been successfully set up.
+func (kc *kubeClient) storeHTTPSEndpoint(ctx context.Context, ep string) error {
+	s := &kubeapi.Secret{
+		Data: map[string][]byte{
+			kubetypes.KeyHTTPSEndpoint: []byte(ep),
+		},
+	}
+	return kc.StrategicMergePatchSecret(ctx, kc.stateSecret, s, "tailscale-container")
 }
 
 // deleteAuthKey deletes the 'authkey' field of the given kube
 // secret. No-op if there is no authkey in the secret.
-func deleteAuthKey(ctx context.Context, secretName string) error {
+func (kc *kubeClient) deleteAuthKey(ctx context.Context) error {
 	// m is a JSON Patch data structure, see https://jsonpatch.com/ or RFC 6902.
 	m := []kubeclient.JSONPatch{
 		{
@@ -61,7 +99,7 @@ func deleteAuthKey(ctx context.Context, secretName string) error {
 			Path: "/data/authkey",
 		},
 	}
-	if err := kc.JSONPatchSecret(ctx, secretName, m); err != nil {
+	if err := kc.JSONPatchResource(ctx, kc.stateSecret, kubeclient.TypeSecrets, m); err != nil {
 		if s, ok := err.(*kubeapi.Status); ok && s.Code == http.StatusUnprocessableEntity {
 			// This is kubernetes-ese for "the field you asked to
 			// delete already doesn't exist", aka no-op.
@@ -72,22 +110,19 @@ func deleteAuthKey(ctx context.Context, secretName string) error {
 	return nil
 }
 
-var kc kubeclient.Client
-
-func initKubeClient(root string) {
-	if root != "/" {
-		// If we are running in a test, we need to set the root path to the fake
-		// service account directory.
-		kubeclient.SetRootPathForTesting(root)
+// storeCapVerUID stores the current capability version of tailscale and, if provided, UID of the Pod in the tailscale
+// state Secret.
+// These two fields are used by the Kubernetes Operator to observe the current capability version of tailscaled running in this container.
+func (kc *kubeClient) storeCapVerUID(ctx context.Context, podUID string) error {
+	capVerS := fmt.Sprintf("%d", tailcfg.CurrentCapabilityVersion)
+	d := map[string][]byte{
+		kubetypes.KeyCapVer: []byte(capVerS),
 	}
-	var err error
-	kc, err = kubeclient.New()
-	if err != nil {
-		log.Fatalf("Error creating kube client: %v", err)
+	if podUID != "" {
+		d[kubetypes.KeyPodUID] = []byte(podUID)
 	}
-	if (root != "/") || os.Getenv("TS_KUBERNETES_READ_API_SERVER_ADDRESS_FROM_ENV") == "true" {
-		// Derive the API server address from the environment variables
-		// Used to set http server in tests, or optionally enabled by flag
-		kc.SetURL(fmt.Sprintf("https://%s:%s", os.Getenv("KUBERNETES_SERVICE_HOST"), os.Getenv("KUBERNETES_SERVICE_PORT_HTTPS")))
+	s := &kubeapi.Secret{
+		Data: d,
 	}
+	return kc.StrategicMergePatchSecret(ctx, kc.stateSecret, s, "tailscale-container")
 }

cmd/containerboot/kube_test.go

@@ -21,7 +21,7 @@ func TestSetupKube(t *testing.T) {
 		cfg     *settings
 		wantErr bool
 		wantCfg *settings
-		kc      kubeclient.Client
+		kc      *kubeClient
 	}{
 		{
 			name: "TS_AUTHKEY set, state Secret exists",
@@ -29,14 +29,14 @@ func TestSetupKube(t *testing.T) {
 				AuthKey:    "foo",
 				KubeSecret: "foo",
 			},
-			kc: &kubeclient.FakeClient{
+			kc: &kubeClient{stateSecret: "foo", Client: &kubeclient.FakeClient{
 				CheckSecretPermissionsImpl: func(context.Context, string) (bool, bool, error) {
 					return false, false, nil
 				},
 				GetSecretImpl: func(context.Context, string) (*kubeapi.Secret, error) {
 					return nil, nil
 				},
-			},
+			}},
 			wantCfg: &settings{
 				AuthKey:    "foo",
 				KubeSecret: "foo",
@@ -48,14 +48,14 @@ func TestSetupKube(t *testing.T) {
 				AuthKey:    "foo",
 				KubeSecret: "foo",
 			},
-			kc: &kubeclient.FakeClient{
+			kc: &kubeClient{stateSecret: "foo", Client: &kubeclient.FakeClient{
 				CheckSecretPermissionsImpl: func(context.Context, string) (bool, bool, error) {
 					return false, true, nil
 				},
 				GetSecretImpl: func(context.Context, string) (*kubeapi.Secret, error) {
 					return nil, &kubeapi.Status{Code: 404}
 				},
-			},
+			}},
 			wantCfg: &settings{
 				AuthKey:    "foo",
 				KubeSecret: "foo",
@@ -67,14 +67,14 @@ func TestSetupKube(t *testing.T) {
 				AuthKey:    "foo",
 				KubeSecret: "foo",
 			},
-			kc: &kubeclient.FakeClient{
+			kc: &kubeClient{stateSecret: "foo", Client: &kubeclient.FakeClient{
 				CheckSecretPermissionsImpl: func(context.Context, string) (bool, bool, error) {
 					return false, false, nil
 				},
 				GetSecretImpl: func(context.Context, string) (*kubeapi.Secret, error) {
 					return nil, &kubeapi.Status{Code: 404}
 				},
-			},
+			}},
 			wantCfg: &settings{
 				AuthKey:    "foo",
 				KubeSecret: "foo",
@@ -87,14 +87,14 @@ func TestSetupKube(t *testing.T) {
 				AuthKey:    "foo",
 				KubeSecret: "foo",
 			},
-			kc: &kubeclient.FakeClient{
+			kc: &kubeClient{stateSecret: "foo", Client: &kubeclient.FakeClient{
 				CheckSecretPermissionsImpl: func(context.Context, string) (bool, bool, error) {
 					return false, false, nil
 				},
 				GetSecretImpl: func(context.Context, string) (*kubeapi.Secret, error) {
 					return nil, &kubeapi.Status{Code: 403}
 				},
-			},
+			}},
 			wantCfg: &settings{
 				AuthKey:    "foo",
 				KubeSecret: "foo",
@@ -111,11 +111,11 @@ func TestSetupKube(t *testing.T) {
 				AuthKey:    "foo",
 				KubeSecret: "foo",
 			},
-			kc: &kubeclient.FakeClient{
+			kc: &kubeClient{stateSecret: "foo", Client: &kubeclient.FakeClient{
 				CheckSecretPermissionsImpl: func(context.Context, string) (bool, bool, error) {
 					return false, false, errors.New("broken")
 				},
-			},
+			}},
 			wantErr: true,
 		},
 		{
@@ -127,14 +127,14 @@ func TestSetupKube(t *testing.T) {
 			wantCfg: &settings{
 				KubeSecret: "foo",
 			},
-			kc: &kubeclient.FakeClient{
+			kc: &kubeClient{stateSecret: "foo", Client: &kubeclient.FakeClient{
 				CheckSecretPermissionsImpl: func(context.Context, string) (bool, bool, error) {
 					return false, true, nil
 				},
 				GetSecretImpl: func(context.Context, string) (*kubeapi.Secret, error) {
 					return nil, &kubeapi.Status{Code: 404}
 				},
-			},
+			}},
 		},
 		{
 			// Interactive login using URL in Pod logs
@@ -145,28 +145,28 @@ func TestSetupKube(t *testing.T) {
 			wantCfg: &settings{
 				KubeSecret: "foo",
 			},
-			kc: &kubeclient.FakeClient{
+			kc: &kubeClient{stateSecret: "foo", Client: &kubeclient.FakeClient{
 				CheckSecretPermissionsImpl: func(context.Context, string) (bool, bool, error) {
 					return false, false, nil
 				},
 				GetSecretImpl: func(context.Context, string) (*kubeapi.Secret, error) {
 					return &kubeapi.Secret{}, nil
 				},
-			},
+			}},
 		},
 		{
 			name: "TS_AUTHKEY not set, state Secret contains auth key, we do not have RBAC to patch it",
 			cfg: &settings{
 				KubeSecret: "foo",
 			},
-			kc: &kubeclient.FakeClient{
+			kc: &kubeClient{stateSecret: "foo", Client: &kubeclient.FakeClient{
 				CheckSecretPermissionsImpl: func(context.Context, string) (bool, bool, error) {
 					return false, false, nil
 				},
 				GetSecretImpl: func(context.Context, string) (*kubeapi.Secret, error) {
 					return &kubeapi.Secret{Data: map[string][]byte{"authkey": []byte("foo")}}, nil
 				},
-			},
+			}},
 			wantCfg: &settings{
 				KubeSecret: "foo",
 			},
@@ -177,14 +177,14 @@ func TestSetupKube(t *testing.T) {
 			cfg: &settings{
 				KubeSecret: "foo",
 			},
-			kc: &kubeclient.FakeClient{
+			kc: &kubeClient{stateSecret: "foo", Client: &kubeclient.FakeClient{
 				CheckSecretPermissionsImpl: func(context.Context, string) (bool, bool, error) {
 					return true, false, nil
 				},
 				GetSecretImpl: func(context.Context, string) (*kubeapi.Secret, error) {
 					return &kubeapi.Secret{Data: map[string][]byte{"authkey": []byte("foo")}}, nil
 				},
-			},
+			}},
 			wantCfg: &settings{
 				KubeSecret:         "foo",
 				AuthKey:            "foo",
@@ -194,9 +194,9 @@ func TestSetupKube(t *testing.T) {
 	}
 
 	for _, tt := range tests {
-		kc = tt.kc
+		kc := tt.kc
 		t.Run(tt.name, func(t *testing.T) {
-			if err := tt.cfg.setupKube(context.Background()); (err != nil) != tt.wantErr {
+			if err := tt.cfg.setupKube(context.Background(), kc); (err != nil) != tt.wantErr {
 				t.Errorf("settings.setupKube() error = %v, wantErr %v", err, tt.wantErr)
 			}
 			if diff := cmp.Diff(*tt.cfg, *tt.wantCfg); diff != "" {

cmd/containerboot/main.go

@@ -52,11 +52,17 @@
 //     ${TS_CERT_DOMAIN}, it will be replaced with the value of the available FQDN.
 //     It cannot be used in conjunction with TS_DEST_IP. The file is watched for changes,
 //     and will be re-applied when it changes.
-//   - TS_HEALTHCHECK_ADDR_PORT: if specified, an HTTP health endpoint will be
-//     served at /healthz at the provided address, which should be in form [<address>]:<port>.
-//     If not set, no health check will be run. If set to :<port>, addr will default to 0.0.0.0
-//     The health endpoint will return 200 OK if this node has at least one tailnet IP address,
-//     otherwise returns 503.
+//   - TS_HEALTHCHECK_ADDR_PORT: deprecated, use TS_ENABLE_HEALTH_CHECK instead and optionally
+//     set TS_LOCAL_ADDR_PORT. Will be removed in 1.82.0.
+//   - TS_LOCAL_ADDR_PORT: the address and port to serve local metrics and health
+//     check endpoints if enabled via TS_ENABLE_METRICS and/or TS_ENABLE_HEALTH_CHECK.
+//     Defaults to [::]:9002, serving on all available interfaces.
+//   - TS_ENABLE_METRICS: if true, a metrics endpoint will be served at /metrics on
+//     the address specified by TS_LOCAL_ADDR_PORT. See https://tailscale.com/kb/1482/client-metrics
+//     for more information on the metrics exposed.
+//   - TS_ENABLE_HEALTH_CHECK: if true, a health check endpoint will be served at /healthz on
+//     the address specified by TS_LOCAL_ADDR_PORT. The health endpoint will return 200
+//     OK if this node has at least one tailnet IP address, otherwise returns 503.
 //     NB: the health criteria might change in the future.
 //   - TS_EXPERIMENTAL_VERSIONED_CONFIG_DIR: if specified, a path to a
 //     directory that containers tailscaled config in file. The config file needs to be
@@ -99,10 +105,10 @@ import (
 	"log"
 	"math"
 	"net"
+	"net/http"
 	"net/netip"
 	"os"
 	"os/signal"
-	"path"
 	"path/filepath"
 	"slices"
 	"strings"
@@ -115,6 +121,7 @@ import (
 	"tailscale.com/client/tailscale"
 	"tailscale.com/ipn"
 	kubeutils "tailscale.com/k8s-operator"
+	"tailscale.com/kube/kubetypes"
 	"tailscale.com/tailcfg"
 	"tailscale.com/types/logger"
 	"tailscale.com/types/ptr"
@@ -161,9 +168,13 @@ func main() {
 	bootCtx, cancel := context.WithTimeout(context.Background(), 60*time.Second)
 	defer cancel()
 
+	var kc *kubeClient
 	if cfg.InKubernetes {
-		initKubeClient(cfg.Root)
-		if err := cfg.setupKube(bootCtx); err != nil {
+		kc, err = newKubeClient(cfg.Root, cfg.KubeSecret)
+		if err != nil {
+			log.Fatalf("error initializing kube client: %v", err)
+		}
+		if err := cfg.setupKube(bootCtx, kc); err != nil {
 			log.Fatalf("error setting up for running on Kubernetes: %v", err)
 		}
 	}
@@ -179,6 +190,34 @@ func main() {
 	}
 	defer killTailscaled()
 
+	var healthCheck *healthz
+	if cfg.HealthCheckAddrPort != "" {
+		mux := http.NewServeMux()
+
+		log.Printf("Running healthcheck endpoint at %s/healthz", cfg.HealthCheckAddrPort)
+		healthCheck = healthHandlers(mux)
+
+		close := runHTTPServer(mux, cfg.HealthCheckAddrPort)
+		defer close()
+	}
+
+	if cfg.localMetricsEnabled() || cfg.localHealthEnabled() {
+		mux := http.NewServeMux()
+
+		if cfg.localMetricsEnabled() {
+			log.Printf("Running metrics endpoint at %s/metrics", cfg.LocalAddrPort)
+			metricsHandlers(mux, client, cfg.DebugAddrPort)
+		}
+
+		if cfg.localHealthEnabled() {
+			log.Printf("Running healthcheck endpoint at %s/healthz", cfg.LocalAddrPort)
+			healthCheck = healthHandlers(mux)
+		}
+
+		close := runHTTPServer(mux, cfg.LocalAddrPort)
+		defer close()
+	}
+
 	if cfg.EnableForwardingOptimizations {
 		if err := client.SetUDPGROForwarding(bootCtx); err != nil {
 			log.Printf("[unexpected] error enabling UDP GRO forwarding: %v", err)
@@ -285,12 +324,18 @@ authLoop:
 		}
 	}
 
+	// Remove any serve config and advertised HTTPS endpoint that may have been set by a previous run of
+	// containerboot, but only if we're providing a new one.
 	if cfg.ServeConfigPath != "" {
-		// Remove any serve config that may have been set by a previous run of
-		// containerboot, but only if we're providing a new one.
+		log.Printf("serve proxy: unsetting previous config")
 		if err := client.SetServeConfig(ctx, new(ipn.ServeConfig)); err != nil {
 			log.Fatalf("failed to unset serve config: %v", err)
 		}
+		if hasKubeStateStore(cfg) {
+			if err := kc.storeHTTPSEndpoint(ctx, ""); err != nil {
+				log.Fatalf("failed to update HTTPS endpoint in tailscale state: %v", err)
+			}
+		}
 	}
 
 	if hasKubeStateStore(cfg) && isTwoStepConfigAuthOnce(cfg) {
@@ -298,16 +343,28 @@ authLoop:
 		// authkey is no longer needed. We don't strictly need to
 		// wipe it, but it's good hygiene.
 		log.Printf("Deleting authkey from kube secret")
-		if err := deleteAuthKey(ctx, cfg.KubeSecret); err != nil {
+		if err := kc.deleteAuthKey(ctx); err != nil {
 			log.Fatalf("deleting authkey from kube secret: %v", err)
 		}
 	}
 
+	if hasKubeStateStore(cfg) {
+		if err := kc.storeCapVerUID(ctx, cfg.PodUID); err != nil {
+			log.Fatalf("storing capability version and UID: %v", err)
+		}
+	}
+
 	w, err = client.WatchIPNBus(ctx, ipn.NotifyInitialNetMap|ipn.NotifyInitialState)
 	if err != nil {
 		log.Fatalf("rewatching tailscaled for updates after auth: %v", err)
 	}
 
+	// If tailscaled config was read from a mounted file, watch the file for updates and reload.
+	cfgWatchErrChan := make(chan error)
+	if cfg.TailscaledConfigFilePath != "" {
+		go watchTailscaledConfigChanges(ctx, cfg.TailscaledConfigFilePath, client, cfgWatchErrChan)
+	}
+
 	var (
 		startupTasksDone       = false
 		currentIPs             deephash.Sum // tailscale IPs assigned to device
@@ -322,12 +379,9 @@ authLoop:
 		certDomain        = new(atomic.Pointer[string])
 		certDomainChanged = make(chan bool, 1)
 
-		h             = &healthz{} // http server for the healthz endpoint
-		healthzRunner = sync.OnceFunc(func() { runHealthz(cfg.HealthCheckAddrPort, h) })
+		triggerWatchServeConfigChanges sync.Once
 	)
-	if cfg.ServeConfigPath != "" {
-		go watchServeConfigChanges(ctx, cfg.ServeConfigPath, certDomainChanged, certDomain, client)
-	}
+
 	var nfr linuxfw.NetfilterRunner
 	if isL3Proxy(cfg) {
 		nfr, err = newNetfilterRunner(log.Printf)
@@ -404,6 +458,8 @@ runLoop:
 			break runLoop
 		case err := <-errChan:
 			log.Fatalf("failed to read from tailscaled: %v", err)
+		case err := <-cfgWatchErrChan:
+			log.Fatalf("failed to watch tailscaled config: %v", err)
 		case n := <-notifyChan:
 			if n.State != nil && *n.State != ipn.Running {
 				// Something's gone wrong and we've left the authenticated state.
@@ -428,7 +484,7 @@ runLoop:
 				// fails.
 				deviceID := n.NetMap.SelfNode.StableID()
 				if hasKubeStateStore(cfg) && deephash.Update(&currentDeviceID, &deviceID) {
-					if err := storeDeviceID(ctx, cfg.KubeSecret, n.NetMap.SelfNode.StableID()); err != nil {
+					if err := kc.storeDeviceID(ctx, n.NetMap.SelfNode.StableID()); err != nil {
 						log.Fatalf("storing device ID in Kubernetes Secret: %v", err)
 					}
 				}
@@ -501,8 +557,11 @@ runLoop:
 					resetTimer(false)
 					backendAddrs = newBackendAddrs
 				}
-				if cfg.ServeConfigPath != "" && len(n.NetMap.DNS.CertDomains) != 0 {
-					cd := n.NetMap.DNS.CertDomains[0]
+				if cfg.ServeConfigPath != "" {
+					cd := certDomainFromNetmap(n.NetMap)
+					if cd == "" {
+						cd = kubetypes.ValueNoHTTPS
+					}
 					prev := certDomain.Swap(ptr.To(cd))
 					if prev == nil || *prev != cd {
 						select {
@@ -544,17 +603,21 @@ runLoop:
 				// TODO (irbekrm): instead of using the IP and FQDN, have some other mechanism for the proxy signal that it is 'Ready'.
 				deviceEndpoints := []any{n.NetMap.SelfNode.Name(), n.NetMap.SelfNode.Addresses()}
 				if hasKubeStateStore(cfg) && deephash.Update(&currentDeviceEndpoints, &deviceEndpoints) {
-					if err := storeDeviceEndpoints(ctx, cfg.KubeSecret, n.NetMap.SelfNode.Name(), n.NetMap.SelfNode.Addresses().AsSlice()); err != nil {
+					if err := kc.storeDeviceEndpoints(ctx, n.NetMap.SelfNode.Name(), n.NetMap.SelfNode.Addresses().AsSlice()); err != nil {
 						log.Fatalf("storing device IPs and FQDN in Kubernetes Secret: %v", err)
 					}
 				}
 
-				if cfg.HealthCheckAddrPort != "" {
-					h.Lock()
-					h.hasAddrs = len(addrs) != 0
-					h.Unlock()
-					healthzRunner()
+				if healthCheck != nil {
+					healthCheck.update(len(addrs) != 0)
 				}
+
+				if cfg.ServeConfigPath != "" {
+					triggerWatchServeConfigChanges.Do(func() {
+						go watchServeConfigChanges(ctx, cfg.ServeConfigPath, certDomainChanged, certDomain, client, kc)
+					})
+				}
+
 				if egressSvcsNotify != nil {
 					egressSvcsNotify <- n
 				}
@@ -731,7 +794,6 @@ func tailscaledConfigFilePath() string {
 		}
 		cv, err := kubeutils.CapVerFromFileName(e.Name())
 		if err != nil {
-			log.Printf("skipping file %q in tailscaled config directory %q: %v", e.Name(), dir, err)
 			continue
 		}
 		if cv > maxCompatVer && cv <= tailcfg.CurrentCapabilityVersion {
@@ -739,8 +801,28 @@ func tailscaledConfigFilePath() string {
 		}
 	}
 	if maxCompatVer == -1 {
-		log.Fatalf("no tailscaled config file found in %q for current capability version %q", dir, tailcfg.CurrentCapabilityVersion)
+		log.Fatalf("no tailscaled config file found in %q for current capability version %d", dir, tailcfg.CurrentCapabilityVersion)
+	}
+	filePath := filepath.Join(dir, kubeutils.TailscaledConfigFileName(maxCompatVer))
+	log.Printf("Using tailscaled config file %q to match current capability version %d", filePath, tailcfg.CurrentCapabilityVersion)
+	return filePath
+}
+
+func runHTTPServer(mux *http.ServeMux, addr string) (close func() error) {
+	ln, err := net.Listen("tcp", addr)
+	if err != nil {
+		log.Fatalf("failed to listen on addr %q: %v", addr, err)
+	}
+	srv := &http.Server{Handler: mux}
+
+	go func() {
+		if err := srv.Serve(ln); err != nil {
+			log.Fatalf("failed running server: %v", err)
+		}
+	}()
+
+	return func() error {
+		err := srv.Shutdown(context.Background())
+		return errors.Join(err, ln.Close())
 	}
-	log.Printf("Using tailscaled config file %q for capability version %q", maxCompatVer, tailcfg.CurrentCapabilityVersion)
-	return path.Join(dir, kubeutils.TailscaledConfigFileName(maxCompatVer))
 }

cmd/containerboot/main_test.go

@@ -31,6 +31,7 @@ import (
 	"github.com/google/go-cmp/cmp"
 	"golang.org/x/sys/unix"
 	"tailscale.com/ipn"
+	"tailscale.com/kube/egressservices"
 	"tailscale.com/tailcfg"
 	"tailscale.com/tstest"
 	"tailscale.com/types/netmap"
@@ -57,6 +58,16 @@ func TestContainerBoot(t *testing.T) {
 	if err != nil {
 		t.Fatalf("error unmarshaling tailscaled config: %v", err)
 	}
+	serveConf := ipn.ServeConfig{TCP: map[uint16]*ipn.TCPPortHandler{80: {HTTP: true}}}
+	serveConfBytes, err := json.Marshal(serveConf)
+	if err != nil {
+		t.Fatalf("error unmarshaling serve config: %v", err)
+	}
+	egressSvcsCfg := egressservices.Configs{"foo": {TailnetTarget: egressservices.TailnetTarget{FQDN: "foo.tailnetxyx.ts.net"}}}
+	egressSvcsCfgBytes, err := json.Marshal(egressSvcsCfg)
+	if err != nil {
+		t.Fatalf("error unmarshaling egress services config: %v", err)
+	}
 
 	dirs := []string{
 		"var/lib",
@@ -73,14 +84,16 @@ func TestContainerBoot(t *testing.T) {
 		}
 	}
 	files := map[string][]byte{
-		"usr/bin/tailscaled":                    fakeTailscaled,
-		"usr/bin/tailscale":                     fakeTailscale,
-		"usr/bin/iptables":                      fakeTailscale,
-		"usr/bin/ip6tables":                     fakeTailscale,
-		"dev/net/tun":                           []byte(""),
-		"proc/sys/net/ipv4/ip_forward":          []byte("0"),
-		"proc/sys/net/ipv6/conf/all/forwarding": []byte("0"),
-		"etc/tailscaled/cap-95.hujson":          tailscaledConfBytes,
+		"usr/bin/tailscaled":                         fakeTailscaled,
+		"usr/bin/tailscale":                          fakeTailscale,
+		"usr/bin/iptables":                           fakeTailscale,
+		"usr/bin/ip6tables":                          fakeTailscale,
+		"dev/net/tun":                                []byte(""),
+		"proc/sys/net/ipv4/ip_forward":               []byte("0"),
+		"proc/sys/net/ipv6/conf/all/forwarding":      []byte("0"),
+		"etc/tailscaled/cap-95.hujson":               tailscaledConfBytes,
+		"etc/tailscaled/serve-config.json":           serveConfBytes,
+		"etc/tailscaled/egress-services-config.json": egressSvcsCfgBytes,
 	}
 	resetFiles := func() {
 		for path, content := range files {
@@ -101,6 +114,26 @@ func TestContainerBoot(t *testing.T) {
 
 	argFile := filepath.Join(d, "args")
 	runningSockPath := filepath.Join(d, "tmp/tailscaled.sock")
+	var localAddrPort, healthAddrPort int
+	for _, p := range []*int{&localAddrPort, &healthAddrPort} {
+		ln, err := net.Listen("tcp", ":0")
+		if err != nil {
+			t.Fatalf("Failed to open listener: %v", err)
+		}
+		if err := ln.Close(); err != nil {
+			t.Fatalf("Failed to close listener: %v", err)
+		}
+		port := ln.Addr().(*net.TCPAddr).Port
+		*p = port
+	}
+	metricsURL := func(port int) string {
+		return fmt.Sprintf("http://127.0.0.1:%d/metrics", port)
+	}
+	healthURL := func(port int) string {
+		return fmt.Sprintf("http://127.0.0.1:%d/healthz", port)
+	}
+
+	capver := fmt.Sprintf("%d", tailcfg.CurrentCapabilityVersion)
 
 	type phase struct {
 		// If non-nil, send this IPN bus notification (and remember it as the
@@ -119,6 +152,8 @@ func TestContainerBoot(t *testing.T) {
 		// WantFatalLog is the fatal log message we expect from containerboot.
 		// If set for a phase, the test will finish on that phase.
 		WantFatalLog string
+
+		EndpointStatuses map[string]int
 	}
 	runningNotify := &ipn.Notify{
 		State: ptr.To(ipn.Running),
@@ -147,6 +182,11 @@ func TestContainerBoot(t *testing.T) {
 						"/usr/bin/tailscaled --socket=/tmp/tailscaled.sock --state=mem: --statedir=/tmp --tun=userspace-networking",
 						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock up --accept-dns=false",
 					},
+					// No metrics or health by default.
+					EndpointStatuses: map[string]int{
+						metricsURL(9002): -1,
+						healthURL(9002):  -1,
+					},
 				},
 				{
 					Notify: runningNotify,
@@ -453,10 +493,11 @@ func TestContainerBoot(t *testing.T) {
 				{
 					Notify: runningNotify,
 					WantKubeSecret: map[string]string{
-						"authkey":     "tskey-key",
-						"device_fqdn": "test-node.test.ts.net",
-						"device_id":   "myID",
-						"device_ips":  `["100.64.0.1"]`,
+						"authkey":          "tskey-key",
+						"device_fqdn":      "test-node.test.ts.net",
+						"device_id":        "myID",
+						"device_ips":       `["100.64.0.1"]`,
+						"tailscale_capver": capver,
 					},
 				},
 			},
@@ -546,9 +587,10 @@ func TestContainerBoot(t *testing.T) {
 						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock set --accept-dns=false",
 					},
 					WantKubeSecret: map[string]string{
-						"device_fqdn": "test-node.test.ts.net",
-						"device_id":   "myID",
-						"device_ips":  `["100.64.0.1"]`,
+						"device_fqdn":      "test-node.test.ts.net",
+						"device_id":        "myID",
+						"device_ips":       `["100.64.0.1"]`,
+						"tailscale_capver": capver,
 					},
 				},
 			},
@@ -575,10 +617,11 @@ func TestContainerBoot(t *testing.T) {
 				{
 					Notify: runningNotify,
 					WantKubeSecret: map[string]string{
-						"authkey":     "tskey-key",
-						"device_fqdn": "test-node.test.ts.net",
-						"device_id":   "myID",
-						"device_ips":  `["100.64.0.1"]`,
+						"authkey":          "tskey-key",
+						"device_fqdn":      "test-node.test.ts.net",
+						"device_id":        "myID",
+						"device_ips":       `["100.64.0.1"]`,
+						"tailscale_capver": capver,
 					},
 				},
 				{
@@ -593,10 +636,11 @@ func TestContainerBoot(t *testing.T) {
 						},
 					},
 					WantKubeSecret: map[string]string{
-						"authkey":     "tskey-key",
-						"device_fqdn": "new-name.test.ts.net",
-						"device_id":   "newID",
-						"device_ips":  `["100.64.0.1"]`,
+						"authkey":          "tskey-key",
+						"device_fqdn":      "new-name.test.ts.net",
+						"device_id":        "newID",
+						"device_ips":       `["100.64.0.1"]`,
+						"tailscale_capver": capver,
 					},
 				},
 			},
@@ -700,6 +744,199 @@ func TestContainerBoot(t *testing.T) {
 				},
 			},
 		},
+		{
+			Name: "metrics_enabled",
+			Env: map[string]string{
+				"TS_LOCAL_ADDR_PORT": fmt.Sprintf("[::]:%d", localAddrPort),
+				"TS_ENABLE_METRICS":  "true",
+			},
+			Phases: []phase{
+				{
+					WantCmds: []string{
+						"/usr/bin/tailscaled --socket=/tmp/tailscaled.sock --state=mem: --statedir=/tmp --tun=userspace-networking",
+						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock up --accept-dns=false",
+					},
+					EndpointStatuses: map[string]int{
+						metricsURL(localAddrPort): 200,
+						healthURL(localAddrPort):  -1,
+					},
+				}, {
+					Notify: runningNotify,
+				},
+			},
+		},
+		{
+			Name: "health_enabled",
+			Env: map[string]string{
+				"TS_LOCAL_ADDR_PORT":     fmt.Sprintf("[::]:%d", localAddrPort),
+				"TS_ENABLE_HEALTH_CHECK": "true",
+			},
+			Phases: []phase{
+				{
+					WantCmds: []string{
+						"/usr/bin/tailscaled --socket=/tmp/tailscaled.sock --state=mem: --statedir=/tmp --tun=userspace-networking",
+						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock up --accept-dns=false",
+					},
+					EndpointStatuses: map[string]int{
+						metricsURL(localAddrPort): -1,
+						healthURL(localAddrPort):  503, // Doesn't start passing until the next phase.
+					},
+				}, {
+					Notify: runningNotify,
+					EndpointStatuses: map[string]int{
+						metricsURL(localAddrPort): -1,
+						healthURL(localAddrPort):  200,
+					},
+				},
+			},
+		},
+		{
+			Name: "metrics_and_health_on_same_port",
+			Env: map[string]string{
+				"TS_LOCAL_ADDR_PORT":     fmt.Sprintf("[::]:%d", localAddrPort),
+				"TS_ENABLE_METRICS":      "true",
+				"TS_ENABLE_HEALTH_CHECK": "true",
+			},
+			Phases: []phase{
+				{
+					WantCmds: []string{
+						"/usr/bin/tailscaled --socket=/tmp/tailscaled.sock --state=mem: --statedir=/tmp --tun=userspace-networking",
+						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock up --accept-dns=false",
+					},
+					EndpointStatuses: map[string]int{
+						metricsURL(localAddrPort): 200,
+						healthURL(localAddrPort):  503, // Doesn't start passing until the next phase.
+					},
+				}, {
+					Notify: runningNotify,
+					EndpointStatuses: map[string]int{
+						metricsURL(localAddrPort): 200,
+						healthURL(localAddrPort):  200,
+					},
+				},
+			},
+		},
+		{
+			Name: "local_metrics_and_deprecated_health",
+			Env: map[string]string{
+				"TS_LOCAL_ADDR_PORT":       fmt.Sprintf("[::]:%d", localAddrPort),
+				"TS_ENABLE_METRICS":        "true",
+				"TS_HEALTHCHECK_ADDR_PORT": fmt.Sprintf("[::]:%d", healthAddrPort),
+			},
+			Phases: []phase{
+				{
+					WantCmds: []string{
+						"/usr/bin/tailscaled --socket=/tmp/tailscaled.sock --state=mem: --statedir=/tmp --tun=userspace-networking",
+						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock up --accept-dns=false",
+					},
+					EndpointStatuses: map[string]int{
+						metricsURL(localAddrPort): 200,
+						healthURL(healthAddrPort): 503, // Doesn't start passing until the next phase.
+					},
+				}, {
+					Notify: runningNotify,
+					EndpointStatuses: map[string]int{
+						metricsURL(localAddrPort): 200,
+						healthURL(healthAddrPort): 200,
+					},
+				},
+			},
+		},
+		{
+			Name: "serve_config_no_kube",
+			Env: map[string]string{
+				"TS_SERVE_CONFIG": filepath.Join(d, "etc/tailscaled/serve-config.json"),
+				"TS_AUTHKEY":      "tskey-key",
+			},
+			Phases: []phase{
+				{
+					WantCmds: []string{
+						"/usr/bin/tailscaled --socket=/tmp/tailscaled.sock --state=mem: --statedir=/tmp --tun=userspace-networking",
+						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock up --accept-dns=false --authkey=tskey-key",
+					},
+				},
+				{
+					Notify: runningNotify,
+				},
+			},
+		},
+		{
+			Name: "serve_config_kube",
+			Env: map[string]string{
+				"KUBERNETES_SERVICE_HOST":       kube.Host,
+				"KUBERNETES_SERVICE_PORT_HTTPS": kube.Port,
+				"TS_SERVE_CONFIG":               filepath.Join(d, "etc/tailscaled/serve-config.json"),
+			},
+			KubeSecret: map[string]string{
+				"authkey": "tskey-key",
+			},
+			Phases: []phase{
+				{
+					WantCmds: []string{
+						"/usr/bin/tailscaled --socket=/tmp/tailscaled.sock --state=kube:tailscale --statedir=/tmp --tun=userspace-networking",
+						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock up --accept-dns=false --authkey=tskey-key",
+					},
+					WantKubeSecret: map[string]string{
+						"authkey": "tskey-key",
+					},
+				},
+				{
+					Notify: runningNotify,
+					WantKubeSecret: map[string]string{
+						"authkey":          "tskey-key",
+						"device_fqdn":      "test-node.test.ts.net",
+						"device_id":        "myID",
+						"device_ips":       `["100.64.0.1"]`,
+						"https_endpoint":   "no-https",
+						"tailscale_capver": capver,
+					},
+				},
+			},
+		},
+		{
+			Name: "egress_svcs_config_kube",
+			Env: map[string]string{
+				"KUBERNETES_SERVICE_HOST":        kube.Host,
+				"KUBERNETES_SERVICE_PORT_HTTPS":  kube.Port,
+				"TS_EGRESS_SERVICES_CONFIG_PATH": filepath.Join(d, "etc/tailscaled/egress-services-config.json"),
+			},
+			KubeSecret: map[string]string{
+				"authkey": "tskey-key",
+			},
+			Phases: []phase{
+				{
+					WantCmds: []string{
+						"/usr/bin/tailscaled --socket=/tmp/tailscaled.sock --state=kube:tailscale --statedir=/tmp --tun=userspace-networking",
+						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock up --accept-dns=false --authkey=tskey-key",
+					},
+					WantKubeSecret: map[string]string{
+						"authkey": "tskey-key",
+					},
+				},
+				{
+					Notify: runningNotify,
+					WantKubeSecret: map[string]string{
+						"authkey":          "tskey-key",
+						"device_fqdn":      "test-node.test.ts.net",
+						"device_id":        "myID",
+						"device_ips":       `["100.64.0.1"]`,
+						"tailscale_capver": capver,
+					},
+				},
+			},
+		},
+		{
+			Name: "egress_svcs_config_no_kube",
+			Env: map[string]string{
+				"TS_EGRESS_SERVICES_CONFIG_PATH": filepath.Join(d, "etc/tailscaled/egress-services-config.json"),
+				"TS_AUTHKEY":                     "tskey-key",
+			},
+			Phases: []phase{
+				{
+					WantFatalLog: "TS_EGRESS_SERVICES_CONFIG_PATH is only supported for Tailscale running on Kubernetes",
+				},
+			},
+		},
 	}
 
 	for _, test := range tests {
@@ -796,7 +1033,26 @@ func TestContainerBoot(t *testing.T) {
 					return nil
 				})
 				if err != nil {
-					t.Fatal(err)
+					t.Fatalf("phase %d: %v", i, err)
+				}
+
+				for url, want := range p.EndpointStatuses {
+					err := tstest.WaitFor(2*time.Second, func() error {
+						resp, err := http.Get(url)
+						if err != nil && want != -1 {
+							return fmt.Errorf("GET %s: %v", url, err)
+						}
+						if want > 0 && resp.StatusCode != want {
+							defer resp.Body.Close()
+							body, _ := io.ReadAll(resp.Body)
+							return fmt.Errorf("GET %s, want %d, got %d\n%s", url, want, resp.StatusCode, string(body))
+						}
+
+						return nil
+					})
+					if err != nil {
+						t.Fatalf("phase %d: %v", i, err)
+					}
 				}
 			}
 			waitLogLine(t, 2*time.Second, cbOut, "Startup complete, waiting for shutdown signal")
@@ -955,6 +1211,12 @@ func (l *localAPI) ServeHTTP(w http.ResponseWriter, r *http.Request) {
 		if r.Method != "GET" {
 			panic(fmt.Sprintf("unsupported method %q", r.Method))
 		}
+	case "/localapi/v0/usermetrics":
+		if r.Method != "GET" {
+			panic(fmt.Sprintf("unsupported method %q", r.Method))
+		}
+		w.Write([]byte("fake metrics"))
+		return
 	default:
 		panic(fmt.Sprintf("unsupported path %q", r.URL.Path))
 	}

cmd/containerboot/metrics.go

@@ -0,0 +1,79 @@
+// Copyright (c) Tailscale Inc & AUTHORS
+// SPDX-License-Identifier: BSD-3-Clause
+
+//go:build linux
+
+package main
+
+import (
+	"fmt"
+	"io"
+	"net/http"
+
+	"tailscale.com/client/tailscale"
+	"tailscale.com/client/tailscale/apitype"
+)
+
+// metrics is a simple metrics HTTP server, if enabled it forwards requests to
+// the tailscaled's LocalAPI usermetrics endpoint at /localapi/v0/usermetrics.
+type metrics struct {
+	debugEndpoint string
+	lc            *tailscale.LocalClient
+}
+
+func proxy(w http.ResponseWriter, r *http.Request, url string, do func(*http.Request) (*http.Response, error)) {
+	req, err := http.NewRequestWithContext(r.Context(), r.Method, url, r.Body)
+	if err != nil {
+		http.Error(w, fmt.Sprintf("failed to construct request: %s", err), http.StatusInternalServerError)
+		return
+	}
+	req.Header = r.Header.Clone()
+
+	resp, err := do(req)
+	if err != nil {
+		http.Error(w, fmt.Sprintf("failed to proxy request: %s", err), http.StatusInternalServerError)
+		return
+	}
+	defer resp.Body.Close()
+
+	for key, val := range resp.Header {
+		for _, v := range val {
+			w.Header().Add(key, v)
+		}
+	}
+	w.WriteHeader(resp.StatusCode)
+	if _, err := io.Copy(w, resp.Body); err != nil {
+		http.Error(w, err.Error(), http.StatusInternalServerError)
+	}
+}
+
+func (m *metrics) handleMetrics(w http.ResponseWriter, r *http.Request) {
+	localAPIURL := "http://" + apitype.LocalAPIHost + "/localapi/v0/usermetrics"
+	proxy(w, r, localAPIURL, m.lc.DoLocalRequest)
+}
+
+func (m *metrics) handleDebug(w http.ResponseWriter, r *http.Request) {
+	if m.debugEndpoint == "" {
+		http.Error(w, "debug endpoint not configured", http.StatusNotFound)
+		return
+	}
+
+	debugURL := "http://" + m.debugEndpoint + r.URL.Path
+	proxy(w, r, debugURL, http.DefaultClient.Do)
+}
+
+// metricsHandlers registers a simple HTTP metrics handler at /metrics, forwarding
+// requests to tailscaled's /localapi/v0/usermetrics API.
+//
+// In 1.78.x and 1.80.x, it also proxies debug paths to tailscaled's debug
+// endpoint if configured to ease migration for a breaking change serving user
+// metrics instead of debug metrics on the "metrics" port.
+func metricsHandlers(mux *http.ServeMux, lc *tailscale.LocalClient, debugAddrPort string) {
+	m := &metrics{
+		lc:            lc,
+		debugEndpoint: debugAddrPort,
+	}
+
+	mux.HandleFunc("GET /metrics", m.handleMetrics)
+	mux.HandleFunc("/debug/", m.handleDebug) // TODO(tomhjp): Remove for 1.82.0 release.
+}

cmd/containerboot/serve.go

@@ -19,6 +19,8 @@ import (
 	"github.com/fsnotify/fsnotify"
 	"tailscale.com/client/tailscale"
 	"tailscale.com/ipn"
+	"tailscale.com/kube/kubetypes"
+	"tailscale.com/types/netmap"
 )
 
 // watchServeConfigChanges watches path for changes, and when it sees one, reads
@@ -26,21 +28,21 @@ import (
 // applies it to lc. It exits when ctx is canceled. cdChanged is a channel that
 // is written to when the certDomain changes, causing the serve config to be
 // re-read and applied.
-func watchServeConfigChanges(ctx context.Context, path string, cdChanged <-chan bool, certDomainAtomic *atomic.Pointer[string], lc *tailscale.LocalClient) {
+func watchServeConfigChanges(ctx context.Context, path string, cdChanged <-chan bool, certDomainAtomic *atomic.Pointer[string], lc *tailscale.LocalClient, kc *kubeClient) {
 	if certDomainAtomic == nil {
-		panic("cd must not be nil")
+		panic("certDomainAtomic must not be nil")
 	}
 	var tickChan <-chan time.Time
 	var eventChan <-chan fsnotify.Event
 	if w, err := fsnotify.NewWatcher(); err != nil {
-		log.Printf("failed to create fsnotify watcher, timer-only mode: %v", err)
+		log.Printf("serve proxy: failed to create fsnotify watcher, timer-only mode: %v", err)
 		ticker := time.NewTicker(5 * time.Second)
 		defer ticker.Stop()
 		tickChan = ticker.C
 	} else {
 		defer w.Close()
 		if err := w.Add(filepath.Dir(path)); err != nil {
-			log.Fatalf("failed to add fsnotify watch: %v", err)
+			log.Fatalf("serve proxy: failed to add fsnotify watch: %v", err)
 		}
 		eventChan = w.Events
 	}
@@ -59,24 +61,72 @@ func watchServeConfigChanges(ctx context.Context, path string, cdChanged <-chan
 			// k8s handles these mounts. So just re-read the file and apply it
 			// if it's changed.
 		}
-		if certDomain == "" {
-			continue
-		}
 		sc, err := readServeConfig(path, certDomain)
 		if err != nil {
-			log.Fatalf("failed to read serve config: %v", err)
+			log.Fatalf("serve proxy: failed to read serve config: %v", err)
+		}
+		if sc == nil {
+			log.Printf("serve proxy: no serve config at %q, skipping", path)
+			continue
 		}
 		if prevServeConfig != nil && reflect.DeepEqual(sc, prevServeConfig) {
 			continue
 		}
-		log.Printf("Applying serve config")
-		if err := lc.SetServeConfig(ctx, sc); err != nil {
-			log.Fatalf("failed to set serve config: %v", err)
+		if err := updateServeConfig(ctx, sc, certDomain, lc); err != nil {
+			log.Fatalf("serve proxy: error updating serve config: %v", err)
+		}
+		if kc != nil && kc.canPatch {
+			if err := kc.storeHTTPSEndpoint(ctx, certDomain); err != nil {
+				log.Fatalf("serve proxy: error storing HTTPS endpoint: %v", err)
+			}
 		}
 		prevServeConfig = sc
 	}
 }
 
+func certDomainFromNetmap(nm *netmap.NetworkMap) string {
+	if len(nm.DNS.CertDomains) == 0 {
+		return ""
+	}
+	return nm.DNS.CertDomains[0]
+}
+
+// localClient is a subset of tailscale.LocalClient that can be mocked for testing.
+type localClient interface {
+	SetServeConfig(context.Context, *ipn.ServeConfig) error
+}
+
+func updateServeConfig(ctx context.Context, sc *ipn.ServeConfig, certDomain string, lc localClient) error {
+	if !isValidHTTPSConfig(certDomain, sc) {
+		return nil
+	}
+	log.Printf("serve proxy: applying serve config")
+	return lc.SetServeConfig(ctx, sc)
+}
+
+func isValidHTTPSConfig(certDomain string, sc *ipn.ServeConfig) bool {
+	if certDomain == kubetypes.ValueNoHTTPS && hasHTTPSEndpoint(sc) {
+		log.Printf(
+			`serve proxy: this node is configured as a proxy that exposes an HTTPS endpoint to tailnet,
+		(perhaps a Kubernetes operator Ingress proxy) but it is not able to issue TLS certs, so this will likely not work.
+		To make it work, ensure that HTTPS is enabled for your tailnet, see https://tailscale.com/kb/1153/enabling-https for more details.`)
+		return false
+	}
+	return true
+}
+
+func hasHTTPSEndpoint(cfg *ipn.ServeConfig) bool {
+	if cfg == nil {
+		return false
+	}
+	for _, tcpCfg := range cfg.TCP {
+		if tcpCfg.HTTPS {
+			return true
+		}
+	}
+	return false
+}
+
 // readServeConfig reads the ipn.ServeConfig from path, replacing
 // ${TS_CERT_DOMAIN} with certDomain.
 func readServeConfig(path, certDomain string) (*ipn.ServeConfig, error) {
@@ -85,8 +135,17 @@ func readServeConfig(path, certDomain string) (*ipn.ServeConfig, error) {
 	}
 	j, err := os.ReadFile(path)
 	if err != nil {
+		if os.IsNotExist(err) {
+			return nil, nil
+		}
 		return nil, err
 	}
+	// Serve config can be provided by users as well as the Kubernetes Operator (for its proxies). User-provided
+	// config could be empty for reasons.
+	if len(j) == 0 {
+		log.Printf("serve proxy: serve config file is empty, skipping")
+		return nil, nil
+	}
 	j = bytes.ReplaceAll(j, []byte("${TS_CERT_DOMAIN}"), []byte(certDomain))
 	var sc ipn.ServeConfig
 	if err := json.Unmarshal(j, &sc); err != nil {

cmd/containerboot/serve_test.go

@@ -0,0 +1,267 @@
+// Copyright (c) Tailscale Inc & AUTHORS
+// SPDX-License-Identifier: BSD-3-Clause
+
+//go:build linux
+
+package main
+
+import (
+	"context"
+	"os"
+	"path/filepath"
+	"testing"
+
+	"github.com/google/go-cmp/cmp"
+	"tailscale.com/client/tailscale"
+	"tailscale.com/ipn"
+	"tailscale.com/kube/kubetypes"
+)
+
+func TestUpdateServeConfig(t *testing.T) {
+	tests := []struct {
+		name       string
+		sc         *ipn.ServeConfig
+		certDomain string
+		wantCall   bool
+	}{
+		{
+			name: "no_https_no_cert_domain",
+			sc: &ipn.ServeConfig{
+				TCP: map[uint16]*ipn.TCPPortHandler{
+					80: {HTTP: true},
+				},
+			},
+			certDomain: kubetypes.ValueNoHTTPS, // tailnet has HTTPS disabled
+			wantCall:   true,                   // should set serve config as it doesn't have HTTPS endpoints
+		},
+		{
+			name: "https_with_cert_domain",
+			sc: &ipn.ServeConfig{
+				TCP: map[uint16]*ipn.TCPPortHandler{
+					443: {HTTPS: true},
+				},
+				Web: map[ipn.HostPort]*ipn.WebServerConfig{
+					"${TS_CERT_DOMAIN}:443": {
+						Handlers: map[string]*ipn.HTTPHandler{
+							"/": {Proxy: "http://10.0.1.100:8080"},
+						},
+					},
+				},
+			},
+			certDomain: "test-node.tailnet.ts.net",
+			wantCall:   true,
+		},
+		{
+			name: "https_without_cert_domain",
+			sc: &ipn.ServeConfig{
+				TCP: map[uint16]*ipn.TCPPortHandler{
+					443: {HTTPS: true},
+				},
+			},
+			certDomain: kubetypes.ValueNoHTTPS,
+			wantCall:   false, // incorrect configuration- should not set serve config
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			fakeLC := &fakeLocalClient{}
+			err := updateServeConfig(context.Background(), tt.sc, tt.certDomain, fakeLC)
+			if err != nil {
+				t.Errorf("updateServeConfig() error = %v", err)
+			}
+			if fakeLC.setServeCalled != tt.wantCall {
+				t.Errorf("SetServeConfig() called = %v, want %v", fakeLC.setServeCalled, tt.wantCall)
+			}
+		})
+	}
+}
+
+func TestReadServeConfig(t *testing.T) {
+	tests := []struct {
+		name       string
+		gotSC      string
+		certDomain string
+		wantSC     *ipn.ServeConfig
+		wantErr    bool
+	}{
+		{
+			name: "empty_file",
+		},
+		{
+			name: "valid_config_with_cert_domain_placeholder",
+			gotSC: `{
+				"TCP": {
+					"443": {
+						"HTTPS": true
+					}
+				},
+				"Web": {
+					"${TS_CERT_DOMAIN}:443": {
+					"Handlers": {
+						"/api": {
+							"Proxy": "https://10.2.3.4/api"
+						}}}}}`,
+			certDomain: "example.com",
+			wantSC: &ipn.ServeConfig{
+				TCP: map[uint16]*ipn.TCPPortHandler{
+					443: {
+						HTTPS: true,
+					},
+				},
+				Web: map[ipn.HostPort]*ipn.WebServerConfig{
+					ipn.HostPort("example.com:443"): {
+						Handlers: map[string]*ipn.HTTPHandler{
+							"/api": {
+								Proxy: "https://10.2.3.4/api",
+							},
+						},
+					},
+				},
+			},
+		},
+		{
+			name: "valid_config_for_http_proxy",
+			gotSC: `{
+				"TCP": {
+					"80": {
+						"HTTP": true
+					}
+				}}`,
+			wantSC: &ipn.ServeConfig{
+				TCP: map[uint16]*ipn.TCPPortHandler{
+					80: {
+						HTTP: true,
+					},
+				},
+			},
+		},
+		{
+			name: "config_without_cert_domain",
+			gotSC: `{
+				"TCP": {
+					"443": {
+						"HTTPS": true
+					}
+				},
+				"Web": {
+					"localhost:443": {
+					"Handlers": {
+						"/api": {
+							"Proxy": "https://10.2.3.4/api"
+						}}}}}`,
+			certDomain: "",
+			wantErr:    false,
+			wantSC: &ipn.ServeConfig{
+				TCP: map[uint16]*ipn.TCPPortHandler{
+					443: {
+						HTTPS: true,
+					},
+				},
+				Web: map[ipn.HostPort]*ipn.WebServerConfig{
+					ipn.HostPort("localhost:443"): {
+						Handlers: map[string]*ipn.HTTPHandler{
+							"/api": {
+								Proxy: "https://10.2.3.4/api",
+							},
+						},
+					},
+				},
+			},
+		},
+		{
+			name:    "invalid_json",
+			gotSC:   "invalid json",
+			wantErr: true,
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			dir := t.TempDir()
+			path := filepath.Join(dir, "serve-config.json")
+			if err := os.WriteFile(path, []byte(tt.gotSC), 0644); err != nil {
+				t.Fatal(err)
+			}
+
+			got, err := readServeConfig(path, tt.certDomain)
+			if (err != nil) != tt.wantErr {
+				t.Errorf("readServeConfig() error = %v, wantErr %v", err, tt.wantErr)
+				return
+			}
+			if !cmp.Equal(got, tt.wantSC) {
+				t.Errorf("readServeConfig() diff (-got +want):\n%s", cmp.Diff(got, tt.wantSC))
+			}
+		})
+	}
+}
+
+type fakeLocalClient struct {
+	*tailscale.LocalClient
+	setServeCalled bool
+}
+
+func (m *fakeLocalClient) SetServeConfig(ctx context.Context, cfg *ipn.ServeConfig) error {
+	m.setServeCalled = true
+	return nil
+}
+
+func TestHasHTTPSEndpoint(t *testing.T) {
+	tests := []struct {
+		name string
+		cfg  *ipn.ServeConfig
+		want bool
+	}{
+		{
+			name: "nil_config",
+			cfg:  nil,
+			want: false,
+		},
+		{
+			name: "empty_config",
+			cfg:  &ipn.ServeConfig{},
+			want: false,
+		},
+		{
+			name: "no_https_endpoints",
+			cfg: &ipn.ServeConfig{
+				TCP: map[uint16]*ipn.TCPPortHandler{
+					80: {
+						HTTPS: false,
+					},
+				},
+			},
+			want: false,
+		},
+		{
+			name: "has_https_endpoint",
+			cfg: &ipn.ServeConfig{
+				TCP: map[uint16]*ipn.TCPPortHandler{
+					443: {
+						HTTPS: true,
+					},
+				},
+			},
+			want: true,
+		},
+		{
+			name: "mixed_endpoints",
+			cfg: &ipn.ServeConfig{
+				TCP: map[uint16]*ipn.TCPPortHandler{
+					80:  {HTTPS: false},
+					443: {HTTPS: true},
+				},
+			},
+			want: true,
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			got := hasHTTPSEndpoint(tt.cfg)
+			if got != tt.want {
+				t.Errorf("hasHTTPSEndpoint() = %v, want %v", got, tt.want)
+			}
+		})
+	}
+}

cmd/containerboot/services.go

@@ -389,7 +389,7 @@ func (ep *egressProxy) setStatus(ctx context.Context, status *egressservices.Sta
 		Path:  fmt.Sprintf("/data/%s", egressservices.KeyEgressServices),
 		Value: bs,
 	}
-	if err := ep.kc.JSONPatchSecret(ctx, ep.stateSecret, []kubeclient.JSONPatch{patch}); err != nil {
+	if err := ep.kc.JSONPatchResource(ctx, ep.stateSecret, kubeclient.TypeSecrets, []kubeclient.JSONPatch{patch}); err != nil {
 		return fmt.Errorf("error patching state Secret: %w", err)
 	}
 	ep.tailnetAddrs = n.NetMap.SelfNode.Addresses().AsSlice()

cmd/containerboot/settings.go

@@ -67,7 +67,12 @@ type settings struct {
 	PodIP               string
 	PodIPv4             string
 	PodIPv6             string
+	PodUID              string
 	HealthCheckAddrPort string
+	LocalAddrPort       string
+	MetricsEnabled      bool
+	HealthCheckEnabled  bool
+	DebugAddrPort       string
 	EgressSvcsCfgPath   string
 }
 
@@ -98,7 +103,12 @@ func configFromEnv() (*settings, error) {
 		PodIP:                                 defaultEnv("POD_IP", ""),
 		EnableForwardingOptimizations:         defaultBool("TS_EXPERIMENTAL_ENABLE_FORWARDING_OPTIMIZATIONS", false),
 		HealthCheckAddrPort:                   defaultEnv("TS_HEALTHCHECK_ADDR_PORT", ""),
+		LocalAddrPort:                         defaultEnv("TS_LOCAL_ADDR_PORT", "[::]:9002"),
+		MetricsEnabled:                        defaultBool("TS_ENABLE_METRICS", false),
+		HealthCheckEnabled:                    defaultBool("TS_ENABLE_HEALTH_CHECK", false),
+		DebugAddrPort:                         defaultEnv("TS_DEBUG_ADDR_PORT", ""),
 		EgressSvcsCfgPath:                     defaultEnv("TS_EGRESS_SERVICES_CONFIG_PATH", ""),
+		PodUID:                                defaultEnv("POD_UID", ""),
 	}
 	podIPs, ok := os.LookupEnv("POD_IPS")
 	if ok {
@@ -171,17 +181,34 @@ func (s *settings) validate() error {
 		return errors.New("TS_EXPERIMENTAL_ENABLE_FORWARDING_OPTIMIZATIONS is not supported in userspace mode")
 	}
 	if s.HealthCheckAddrPort != "" {
+		log.Printf("[warning] TS_HEALTHCHECK_ADDR_PORT is deprecated and will be removed in 1.82.0. Please use TS_ENABLE_HEALTH_CHECK and optionally TS_LOCAL_ADDR_PORT instead.")
 		if _, err := netip.ParseAddrPort(s.HealthCheckAddrPort); err != nil {
-			return fmt.Errorf("error parsing TS_HEALTH_CHECK_ADDR_PORT value %q: %w", s.HealthCheckAddrPort, err)
+			return fmt.Errorf("error parsing TS_HEALTHCHECK_ADDR_PORT value %q: %w", s.HealthCheckAddrPort, err)
 		}
 	}
+	if s.localMetricsEnabled() || s.localHealthEnabled() {
+		if _, err := netip.ParseAddrPort(s.LocalAddrPort); err != nil {
+			return fmt.Errorf("error parsing TS_LOCAL_ADDR_PORT value %q: %w", s.LocalAddrPort, err)
+		}
+	}
+	if s.DebugAddrPort != "" {
+		if _, err := netip.ParseAddrPort(s.DebugAddrPort); err != nil {
+			return fmt.Errorf("error parsing TS_DEBUG_ADDR_PORT value %q: %w", s.DebugAddrPort, err)
+		}
+	}
+	if s.HealthCheckEnabled && s.HealthCheckAddrPort != "" {
+		return errors.New("TS_HEALTHCHECK_ADDR_PORT is deprecated and will be removed in 1.82.0, use TS_ENABLE_HEALTH_CHECK and optionally TS_LOCAL_ADDR_PORT")
+	}
+	if s.EgressSvcsCfgPath != "" && !(s.InKubernetes && s.KubeSecret != "") {
+		return errors.New("TS_EGRESS_SERVICES_CONFIG_PATH is only supported for Tailscale running on Kubernetes")
+	}
 	return nil
 }
 
 // setupKube is responsible for doing any necessary configuration and checks to
 // ensure that tailscale state storage and authentication mechanism will work on
 // Kubernetes.
-func (cfg *settings) setupKube(ctx context.Context) error {
+func (cfg *settings) setupKube(ctx context.Context, kc *kubeClient) error {
 	if cfg.KubeSecret == "" {
 		return nil
 	}
@@ -190,6 +217,7 @@ func (cfg *settings) setupKube(ctx context.Context) error {
 		return fmt.Errorf("some Kubernetes permissions are missing, please check your RBAC configuration: %v", err)
 	}
 	cfg.KubernetesCanPatch = canPatch
+	kc.canPatch = canPatch
 
 	s, err := kc.GetSecret(ctx, cfg.KubeSecret)
 	if err != nil {
@@ -272,6 +300,14 @@ func hasKubeStateStore(cfg *settings) bool {
 	return cfg.InKubernetes && cfg.KubernetesCanPatch && cfg.KubeSecret != ""
 }
 
+func (cfg *settings) localMetricsEnabled() bool {
+	return cfg.LocalAddrPort != "" && cfg.MetricsEnabled
+}
+
+func (cfg *settings) localHealthEnabled() bool {
+	return cfg.LocalAddrPort != "" && cfg.HealthCheckEnabled
+}
+
 // defaultEnv returns the value of the given envvar name, or defVal if
 // unset.
 func defaultEnv(name, defVal string) string {

cmd/containerboot/tailscaled.go

@@ -13,10 +13,13 @@ import (
 	"log"
 	"os"
 	"os/exec"
+	"path/filepath"
+	"reflect"
 	"strings"
 	"syscall"
 	"time"
 
+	"github.com/fsnotify/fsnotify"
 	"tailscale.com/client/tailscale"
 )
 
@@ -90,6 +93,12 @@ func tailscaledArgs(cfg *settings) []string {
 	if cfg.TailscaledConfigFilePath != "" {
 		args = append(args, "--config="+cfg.TailscaledConfigFilePath)
 	}
+	// Once enough proxy versions have been released for all the supported
+	// versions to understand this cfg setting, the operator can stop
+	// setting TS_TAILSCALED_EXTRA_ARGS for the debug flag.
+	if cfg.DebugAddrPort != "" && !strings.Contains(cfg.DaemonExtraArgs, cfg.DebugAddrPort) {
+		args = append(args, "--debug="+cfg.DebugAddrPort)
+	}
 	if cfg.DaemonExtraArgs != "" {
 		args = append(args, strings.Fields(cfg.DaemonExtraArgs)...)
 	}
@@ -160,3 +169,70 @@ func tailscaleSet(ctx context.Context, cfg *settings) error {
 	}
 	return nil
 }
+
+func watchTailscaledConfigChanges(ctx context.Context, path string, lc *tailscale.LocalClient, errCh chan<- error) {
+	var (
+		tickChan          <-chan time.Time
+		tailscaledCfgDir  = filepath.Dir(path)
+		prevTailscaledCfg []byte
+	)
+	w, err := fsnotify.NewWatcher()
+	if err != nil {
+		log.Printf("tailscaled config watch: failed to create fsnotify watcher, timer-only mode: %v", err)
+		ticker := time.NewTicker(5 * time.Second)
+		defer ticker.Stop()
+		tickChan = ticker.C
+	} else {
+		defer w.Close()
+		if err := w.Add(tailscaledCfgDir); err != nil {
+			errCh <- fmt.Errorf("failed to add fsnotify watch: %w", err)
+			return
+		}
+	}
+	b, err := os.ReadFile(path)
+	if err != nil {
+		errCh <- fmt.Errorf("error reading configfile: %w", err)
+		return
+	}
+	prevTailscaledCfg = b
+	// kubelet mounts Secrets to Pods using a series of symlinks, one of
+	// which is <mount-dir>/..data that Kubernetes recommends consumers to
+	// use if they need to monitor changes
+	// https://github.com/kubernetes/kubernetes/blob/v1.28.1/pkg/volume/util/atomic_writer.go#L39-L61
+	const kubeletMountedCfg = "..data"
+	toWatch := filepath.Join(tailscaledCfgDir, kubeletMountedCfg)
+	for {
+		select {
+		case <-ctx.Done():
+			return
+		case err := <-w.Errors:
+			errCh <- fmt.Errorf("watcher error: %w", err)
+			return
+		case <-tickChan:
+		case event := <-w.Events:
+			if event.Name != toWatch {
+				continue
+			}
+		}
+		b, err := os.ReadFile(path)
+		if err != nil {
+			errCh <- fmt.Errorf("error reading configfile: %w", err)
+			return
+		}
+		// For some proxy types the mounted volume also contains tailscaled state and other files. We
+		// don't want to reload config unnecessarily on unrelated changes to these files.
+		if reflect.DeepEqual(b, prevTailscaledCfg) {
+			continue
+		}
+		prevTailscaledCfg = b
+		log.Printf("tailscaled config watch: ensuring that config is up to date")
+		ok, err := lc.ReloadConfig(ctx)
+		if err != nil {
+			errCh <- fmt.Errorf("error reloading tailscaled config: %w", err)
+			return
+		}
+		if ok {
+			log.Printf("tailscaled config watch: config was reloaded")
+		}
+	}
+}

cmd/derper/bootstrap_dns_test.go

@@ -20,10 +20,10 @@ import (
 )
 
 func BenchmarkHandleBootstrapDNS(b *testing.B) {
-	tstest.Replace(b, bootstrapDNS, "log.tailscale.io,login.tailscale.com,controlplane.tailscale.com,login.us.tailscale.com")
+	tstest.Replace(b, bootstrapDNS, "log.tailscale.com,login.tailscale.com,controlplane.tailscale.com,login.us.tailscale.com")
 	refreshBootstrapDNS()
 	w := new(bitbucketResponseWriter)
-	req, _ := http.NewRequest("GET", "https://localhost/bootstrap-dns?q="+url.QueryEscape("log.tailscale.io"), nil)
+	req, _ := http.NewRequest("GET", "https://localhost/bootstrap-dns?q="+url.QueryEscape("log.tailscale.com"), nil)
 	b.ReportAllocs()
 	b.ResetTimer()
 	b.RunParallel(func(b *testing.PB) {
@@ -63,7 +63,7 @@ func TestUnpublishedDNS(t *testing.T) {
 	nettest.SkipIfNoNetwork(t)
 
 	const published = "login.tailscale.com"
-	const unpublished = "log.tailscale.io"
+	const unpublished = "log.tailscale.com"
 
 	prev1, prev2 := *bootstrapDNS, *unpublishedDNS
 	*bootstrapDNS = published
@@ -119,18 +119,18 @@ func TestUnpublishedDNSEmptyList(t *testing.T) {
 
 	unpublishedDNSCache.Store(&dnsEntryMap{
 		IPs: map[string][]net.IP{
-			"log.tailscale.io":           {},
+			"log.tailscale.com":          {},
 			"controlplane.tailscale.com": {net.IPv4(1, 2, 3, 4)},
 		},
 		Percent: map[string]float64{
-			"log.tailscale.io":           1.0,
+			"log.tailscale.com":          1.0,
 			"controlplane.tailscale.com": 1.0,
 		},
 	})
 
 	t.Run("CacheMiss", func(t *testing.T) {
 		// One domain in map but empty, one not in map at all
-		for _, q := range []string{"log.tailscale.io", "login.tailscale.com"} {
+		for _, q := range []string{"log.tailscale.com", "login.tailscale.com"} {
 			resetMetrics()
 			ips := getBootstrapDNS(t, q)
 

cmd/derper/cert.go

@@ -8,6 +8,7 @@ import (
 	"crypto/x509"
 	"errors"
 	"fmt"
+	"net"
 	"net/http"
 	"path/filepath"
 	"regexp"
@@ -53,8 +54,9 @@ func certProviderByCertMode(mode, dir, hostname string) (certProvider, error) {
 }
 
 type manualCertManager struct {
-	cert     *tls.Certificate
-	hostname string
+	cert       *tls.Certificate
+	hostname   string // hostname or IP address of server
+	noHostname bool   // whether hostname is an IP address
 }
 
 // NewManualCertManager returns a cert provider which read certificate by given hostname on create.
@@ -74,7 +76,11 @@ func NewManualCertManager(certdir, hostname string) (certProvider, error) {
 	if err := x509Cert.VerifyHostname(hostname); err != nil {
 		return nil, fmt.Errorf("cert invalid for hostname %q: %w", hostname, err)
 	}
-	return &manualCertManager{cert: &cert, hostname: hostname}, nil
+	return &manualCertManager{
+		cert:       &cert,
+		hostname:   hostname,
+		noHostname: net.ParseIP(hostname) != nil,
+	}, nil
 }
 
 func (m *manualCertManager) TLSConfig() *tls.Config {
@@ -88,7 +94,7 @@ func (m *manualCertManager) TLSConfig() *tls.Config {
 }
 
 func (m *manualCertManager) getCertificate(hi *tls.ClientHelloInfo) (*tls.Certificate, error) {
-	if hi.ServerName != m.hostname {
+	if hi.ServerName != m.hostname && !m.noHostname {
 		return nil, fmt.Errorf("cert mismatch with hostname: %q", hi.ServerName)
 	}
 

cmd/derper/cert_test.go

@@ -0,0 +1,97 @@
+// Copyright (c) Tailscale Inc & AUTHORS
+// SPDX-License-Identifier: BSD-3-Clause
+
+package main
+
+import (
+	"crypto/ecdsa"
+	"crypto/elliptic"
+	"crypto/rand"
+	"crypto/tls"
+	"crypto/x509"
+	"crypto/x509/pkix"
+	"encoding/pem"
+	"math/big"
+	"net"
+	"os"
+	"path/filepath"
+	"testing"
+	"time"
+)
+
+// Verify that in --certmode=manual mode, we can use a bare IP address
+// as the --hostname and that GetCertificate will return it.
+func TestCertIP(t *testing.T) {
+	dir := t.TempDir()
+	const hostname = "1.2.3.4"
+
+	priv, err := ecdsa.GenerateKey(elliptic.P224(), rand.Reader)
+	if err != nil {
+		t.Fatal(err)
+	}
+	serialNumberLimit := new(big.Int).Lsh(big.NewInt(1), 128)
+	serialNumber, err := rand.Int(rand.Reader, serialNumberLimit)
+	if err != nil {
+		t.Fatal(err)
+	}
+	ip := net.ParseIP(hostname)
+	if ip == nil {
+		t.Fatalf("invalid IP address %q", hostname)
+	}
+	template := &x509.Certificate{
+		SerialNumber: serialNumber,
+		Subject: pkix.Name{
+			Organization: []string{"Tailscale Test Corp"},
+		},
+		NotBefore: time.Now(),
+		NotAfter:  time.Now().Add(30 * 24 * time.Hour),
+
+		KeyUsage:              x509.KeyUsageDigitalSignature,
+		ExtKeyUsage:           []x509.ExtKeyUsage{x509.ExtKeyUsageServerAuth},
+		BasicConstraintsValid: true,
+		IPAddresses:           []net.IP{ip},
+	}
+	derBytes, err := x509.CreateCertificate(rand.Reader, template, template, &priv.PublicKey, priv)
+	if err != nil {
+		t.Fatal(err)
+	}
+	certOut, err := os.Create(filepath.Join(dir, hostname+".crt"))
+	if err != nil {
+		t.Fatal(err)
+	}
+	if err := pem.Encode(certOut, &pem.Block{Type: "CERTIFICATE", Bytes: derBytes}); err != nil {
+		t.Fatalf("Failed to write data to cert.pem: %v", err)
+	}
+	if err := certOut.Close(); err != nil {
+		t.Fatalf("Error closing cert.pem: %v", err)
+	}
+
+	keyOut, err := os.OpenFile(filepath.Join(dir, hostname+".key"), os.O_WRONLY|os.O_CREATE|os.O_TRUNC, 0600)
+	if err != nil {
+		t.Fatal(err)
+	}
+	privBytes, err := x509.MarshalPKCS8PrivateKey(priv)
+	if err != nil {
+		t.Fatalf("Unable to marshal private key: %v", err)
+	}
+	if err := pem.Encode(keyOut, &pem.Block{Type: "PRIVATE KEY", Bytes: privBytes}); err != nil {
+		t.Fatalf("Failed to write data to key.pem: %v", err)
+	}
+	if err := keyOut.Close(); err != nil {
+		t.Fatalf("Error closing key.pem: %v", err)
+	}
+
+	cp, err := certProviderByCertMode("manual", dir, hostname)
+	if err != nil {
+		t.Fatal(err)
+	}
+	back, err := cp.TLSConfig().GetCertificate(&tls.ClientHelloInfo{
+		ServerName: "", // no SNI
+	})
+	if err != nil {
+		t.Fatalf("GetCertificate: %v", err)
+	}
+	if back == nil {
+		t.Fatalf("GetCertificate returned nil")
+	}
+}

cmd/derper/depaware.txt

@@ -27,9 +27,7 @@ tailscale.com/cmd/derper dependencies: (generated by github.com/tailscale/depawa
    L    github.com/google/nftables/expr                              from github.com/google/nftables+
    L    github.com/google/nftables/internal/parseexprfunc            from github.com/google/nftables+
    L    github.com/google/nftables/xt                                from github.com/google/nftables/expr+
-        github.com/google/uuid                                       from tailscale.com/util/fastuuid
         github.com/hdevalence/ed25519consensus                       from tailscale.com/tka
-   L    github.com/josharian/native                                  from github.com/mdlayher/netlink+
    L 💣 github.com/jsimonetti/rtnetlink                              from tailscale.com/net/netmon
    L    github.com/jsimonetti/rtnetlink/internal/unix                from github.com/jsimonetti/rtnetlink
    L 💣 github.com/mdlayher/netlink                                  from github.com/google/nftables+
@@ -37,11 +35,11 @@ tailscale.com/cmd/derper dependencies: (generated by github.com/tailscale/depawa
    L    github.com/mdlayher/netlink/nltest                           from github.com/google/nftables
    L 💣 github.com/mdlayher/socket                                   from github.com/mdlayher/netlink
      💣 github.com/mitchellh/go-ps                                   from tailscale.com/safesocket
+        github.com/munnerz/goautoneg                                 from github.com/prometheus/common/expfmt
      💣 github.com/prometheus/client_golang/prometheus               from tailscale.com/tsweb/promvarz
         github.com/prometheus/client_golang/prometheus/internal      from github.com/prometheus/client_golang/prometheus
         github.com/prometheus/client_model/go                        from github.com/prometheus/client_golang/prometheus+
         github.com/prometheus/common/expfmt                          from github.com/prometheus/client_golang/prometheus+
-        github.com/prometheus/common/internal/bitbucket.org/ww/goautoneg from github.com/prometheus/common/expfmt
         github.com/prometheus/common/model                           from github.com/prometheus/client_golang/prometheus+
   LD    github.com/prometheus/procfs                                 from github.com/prometheus/client_golang/prometheus
   LD    github.com/prometheus/procfs/internal/fs                     from github.com/prometheus/procfs
@@ -87,7 +85,7 @@ tailscale.com/cmd/derper dependencies: (generated by github.com/tailscale/depawa
         google.golang.org/protobuf/runtime/protoimpl                 from github.com/prometheus/client_model/go+
         google.golang.org/protobuf/types/known/timestamppb           from github.com/prometheus/client_golang/prometheus+
         tailscale.com                                                from tailscale.com/version
-        tailscale.com/atomicfile                                     from tailscale.com/cmd/derper+
+     💣 tailscale.com/atomicfile                                     from tailscale.com/cmd/derper+
         tailscale.com/client/tailscale                               from tailscale.com/derp
         tailscale.com/client/tailscale/apitype                       from tailscale.com/client/tailscale
         tailscale.com/derp                                           from tailscale.com/cmd/derper+
@@ -101,6 +99,7 @@ tailscale.com/cmd/derper dependencies: (generated by github.com/tailscale/depawa
         tailscale.com/ipn/ipnstate                                   from tailscale.com/client/tailscale+
         tailscale.com/kube/kubetypes                                 from tailscale.com/envknob
         tailscale.com/metrics                                        from tailscale.com/cmd/derper+
+        tailscale.com/net/bakedroots                                 from tailscale.com/net/tlsdial
         tailscale.com/net/dnscache                                   from tailscale.com/derp/derphttp
         tailscale.com/net/ktimeout                                   from tailscale.com/cmd/derper
         tailscale.com/net/netaddr                                    from tailscale.com/ipn+
@@ -116,7 +115,7 @@ tailscale.com/cmd/derper dependencies: (generated by github.com/tailscale/depawa
         tailscale.com/net/tlsdial/blockblame                         from tailscale.com/net/tlsdial
         tailscale.com/net/tsaddr                                     from tailscale.com/ipn+
      💣 tailscale.com/net/tshttpproxy                                from tailscale.com/derp/derphttp+
-        tailscale.com/net/wsconn                                     from tailscale.com/cmd/derper+
+        tailscale.com/net/wsconn                                     from tailscale.com/cmd/derper
         tailscale.com/paths                                          from tailscale.com/client/tailscale
      💣 tailscale.com/safesocket                                     from tailscale.com/client/tailscale
         tailscale.com/syncs                                          from tailscale.com/cmd/derper+
@@ -140,6 +139,7 @@ tailscale.com/cmd/derper dependencies: (generated by github.com/tailscale/depawa
         tailscale.com/types/persist                                  from tailscale.com/ipn
         tailscale.com/types/preftype                                 from tailscale.com/ipn
         tailscale.com/types/ptr                                      from tailscale.com/hostinfo+
+        tailscale.com/types/result                                   from tailscale.com/util/lineiter
         tailscale.com/types/structs                                  from tailscale.com/ipn+
         tailscale.com/types/tkatype                                  from tailscale.com/client/tailscale+
         tailscale.com/types/views                                    from tailscale.com/ipn+
@@ -151,14 +151,14 @@ tailscale.com/cmd/derper dependencies: (generated by github.com/tailscale/depawa
      💣 tailscale.com/util/deephash                                  from tailscale.com/util/syspolicy/setting
    L 💣 tailscale.com/util/dirwalk                                   from tailscale.com/metrics
         tailscale.com/util/dnsname                                   from tailscale.com/hostinfo+
-        tailscale.com/util/fastuuid                                  from tailscale.com/tsweb
      💣 tailscale.com/util/hashx                                     from tailscale.com/util/deephash
         tailscale.com/util/httpm                                     from tailscale.com/client/tailscale
-        tailscale.com/util/lineread                                  from tailscale.com/hostinfo+
+        tailscale.com/util/lineiter                                  from tailscale.com/hostinfo+
    L    tailscale.com/util/linuxfw                                   from tailscale.com/net/netns
         tailscale.com/util/mak                                       from tailscale.com/health+
         tailscale.com/util/multierr                                  from tailscale.com/health+
         tailscale.com/util/nocasemaps                                from tailscale.com/types/ipproto
+        tailscale.com/util/rands                                     from tailscale.com/tsweb
         tailscale.com/util/set                                       from tailscale.com/derp+
         tailscale.com/util/singleflight                              from tailscale.com/net/dnscache
         tailscale.com/util/slicesx                                   from tailscale.com/cmd/derper+
@@ -204,7 +204,7 @@ tailscale.com/cmd/derper dependencies: (generated by github.com/tailscale/depawa
         golang.org/x/net/proxy                                       from tailscale.com/net/netns
    D    golang.org/x/net/route                                       from net+
         golang.org/x/sync/errgroup                                   from github.com/mdlayher/socket+
-        golang.org/x/sys/cpu                                         from github.com/josharian/native+
+        golang.org/x/sys/cpu                                         from golang.org/x/crypto/argon2+
   LD    golang.org/x/sys/unix                                        from github.com/google/nftables+
    W    golang.org/x/sys/windows                                     from github.com/dblohm7/wingoes+
    W    golang.org/x/sys/windows/registry                            from github.com/dblohm7/wingoes+
@@ -243,7 +243,6 @@ tailscale.com/cmd/derper dependencies: (generated by github.com/tailscale/depawa
         crypto/tls                                                   from golang.org/x/crypto/acme+
         crypto/x509                                                  from crypto/tls+
         crypto/x509/pkix                                             from crypto/x509+
-        database/sql/driver                                          from github.com/google/uuid
         embed                                                        from crypto/internal/nistec+
         encoding                                                     from encoding/json+
         encoding/asn1                                                from crypto/x509+
@@ -263,9 +262,10 @@ tailscale.com/cmd/derper dependencies: (generated by github.com/tailscale/depawa
         hash/fnv                                                     from google.golang.org/protobuf/internal/detrand
         hash/maphash                                                 from go4.org/mem
         html                                                         from net/http/pprof+
+        html/template                                                from tailscale.com/cmd/derper
         io                                                           from bufio+
         io/fs                                                        from crypto/x509+
-        io/ioutil                                                    from github.com/mitchellh/go-ps+
+   L    io/ioutil                                                    from github.com/mitchellh/go-ps+
         iter                                                         from maps+
         log                                                          from expvar+
         log/internal                                                 from log
@@ -274,7 +274,7 @@ tailscale.com/cmd/derper dependencies: (generated by github.com/tailscale/depawa
         math/big                                                     from crypto/dsa+
         math/bits                                                    from compress/flate+
         math/rand                                                    from github.com/mdlayher/netlink+
-        math/rand/v2                                                 from tailscale.com/util/fastuuid+
+        math/rand/v2                                                 from internal/concurrent+
         mime                                                         from github.com/prometheus/common/expfmt+
         mime/multipart                                               from net/http
         mime/quotedprintable                                         from mime/multipart
@@ -307,6 +307,8 @@ tailscale.com/cmd/derper dependencies: (generated by github.com/tailscale/depawa
         sync/atomic                                                  from context+
         syscall                                                      from crypto/rand+
         text/tabwriter                                               from runtime/pprof
+        text/template                                                from html/template
+        text/template/parse                                          from html/template+
         time                                                         from compress/gzip+
         unicode                                                      from bytes+
         unicode/utf16                                                from crypto/x509+

cmd/derper/derper.go

@@ -19,6 +19,7 @@ import (
 	"expvar"
 	"flag"
 	"fmt"
+	"html/template"
 	"io"
 	"log"
 	"math"
@@ -57,12 +58,12 @@ var (
 	configPath  = flag.String("c", "", "config file path")
 	certMode    = flag.String("certmode", "letsencrypt", "mode for getting a cert. possible options: manual, letsencrypt")
 	certDir     = flag.String("certdir", tsweb.DefaultCertDir("derper-certs"), "directory to store LetsEncrypt certs, if addr's port is :443")
-	hostname    = flag.String("hostname", "derp.tailscale.com", "LetsEncrypt host name, if addr's port is :443")
+	hostname    = flag.String("hostname", "derp.tailscale.com", "LetsEncrypt host name, if addr's port is :443. When --certmode=manual, this can be an IP address to avoid SNI checks")
 	runSTUN     = flag.Bool("stun", true, "whether to run a STUN server. It will bind to the same IP (if any) as the --addr flag value.")
 	runDERP     = flag.Bool("derp", true, "whether to run a DERP server. The only reason to set this false is if you're decommissioning a server but want to keep its bootstrap DNS functionality still running.")
 
 	meshPSKFile     = flag.String("mesh-psk-file", defaultMeshPSKFile(), "if non-empty, path to file containing the mesh pre-shared key file. It should contain some hex string; whitespace is trimmed.")
-	meshWith        = flag.String("mesh-with", "", "optional comma-separated list of hostnames to mesh with; the server's own hostname can be in the list")
+	meshWith        = flag.String("mesh-with", "", "optional comma-separated list of hostnames to mesh with; the server's own hostname can be in the list. If an entry contains a slash, the second part names a hostname to be used when dialing the target.")
 	bootstrapDNS    = flag.String("bootstrap-dns-names", "", "optional comma-separated list of hostnames to make available at /bootstrap-dns")
 	unpublishedDNS  = flag.String("unpublished-bootstrap-dns-names", "", "optional comma-separated list of hostnames to make available at /bootstrap-dns and not publish in the list. If an entry contains a slash, the second part names a DNS record to poll for its TXT record with a `0` to `100` value for rollout percentage.")
 	verifyClients   = flag.Bool("verify-clients", false, "verify clients to this DERP server through a local tailscaled instance.")
@@ -76,6 +77,8 @@ var (
 	tcpKeepAlive = flag.Duration("tcp-keepalive-time", 10*time.Minute, "TCP keepalive time")
 	// tcpUserTimeout is intentionally short, so that hung connections are cleaned up promptly. DERPs should be nearby users.
 	tcpUserTimeout = flag.Duration("tcp-user-timeout", 15*time.Second, "TCP user timeout")
+	// tcpWriteTimeout is the timeout for writing to client TCP connections. It does not apply to mesh connections.
+	tcpWriteTimeout = flag.Duration("tcp-write-timeout", derp.DefaultTCPWiteTimeout, "TCP write timeout; 0 results in no timeout being set on writes")
 )
 
 var (
@@ -172,6 +175,7 @@ func main() {
 	s.SetVerifyClient(*verifyClients)
 	s.SetVerifyClientURL(*verifyClientURL)
 	s.SetVerifyClientURLFailOpen(*verifyFailOpen)
+	s.SetTCPWriteTimeout(*tcpWriteTimeout)
 
 	if *meshPSKFile != "" {
 		b, err := os.ReadFile(*meshPSKFile)
@@ -212,25 +216,16 @@ func main() {
 		tsweb.AddBrowserHeaders(w)
 		w.Header().Set("Content-Type", "text/html; charset=utf-8")
 		w.WriteHeader(200)
-		io.WriteString(w, `<html><body>
-<h1>DERP</h1>
-<p>
-  This is a <a href="https://tailscale.com/">Tailscale</a> DERP server.
-</p>
-<p>
-  Documentation:
-</p>
-<ul>
-  <li><a href="https://tailscale.com/kb/1232/derp-servers">About DERP</a></li>
-  <li><a href="https://pkg.go.dev/tailscale.com/derp">Protocol & Go docs</a></li>
-  <li><a href="https://github.com/tailscale/tailscale/tree/main/cmd/derper#derp">How to run a DERP server</a></li>
-</ul>
-`)
-		if !*runDERP {
-			io.WriteString(w, `<p>Status: <b>disabled</b></p>`)
-		}
-		if tsweb.AllowDebugAccess(r) {
-			io.WriteString(w, "<p>Debug info at <a href='/debug/'>/debug/</a>.</p>\n")
+		err := homePageTemplate.Execute(w, templateData{
+			ShowAbuseInfo: validProdHostname.MatchString(*hostname),
+			Disabled:      !*runDERP,
+			AllowDebug:    tsweb.AllowDebugAccess(r),
+		})
+		if err != nil {
+			if r.Context().Err() == nil {
+				log.Printf("homePageTemplate.Execute: %v", err)
+			}
+			return
 		}
 	}))
 	mux.Handle("/robots.txt", http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
@@ -468,3 +463,52 @@ func init() {
 		return 0
 	}))
 }
+
+type templateData struct {
+	ShowAbuseInfo bool
+	Disabled      bool
+	AllowDebug    bool
+}
+
+// homePageTemplate renders the home page using [templateData].
+var homePageTemplate = template.Must(template.New("home").Parse(`<html><body>
+<h1>DERP</h1>
+<p>
+  This is a <a href="https://tailscale.com/">Tailscale</a> DERP server.
+</p>
+
+<p>
+  It provides STUN, interactive connectivity establishment, and relaying of end-to-end encrypted traffic
+  for Tailscale clients.
+</p>
+
+{{if .ShowAbuseInfo }}
+<p>
+  If you suspect abuse, please contact <a href="mailto:security@tailscale.com">security@tailscale.com</a>.
+</p>
+{{end}}
+
+<p>
+  Documentation:
+</p>
+
+<ul>
+{{if .ShowAbuseInfo }}
+  <li><a href="https://tailscale.com/security-policies">Tailscale Security Policies</a></li>
+  <li><a href="https://tailscale.com/tailscale-aup">Tailscale Acceptable Use Policies</a></li>
+{{end}}
+  <li><a href="https://tailscale.com/kb/1232/derp-servers">About DERP</a></li>
+  <li><a href="https://pkg.go.dev/tailscale.com/derp">Protocol & Go docs</a></li>
+  <li><a href="https://github.com/tailscale/tailscale/tree/main/cmd/derper#derp">How to run a DERP server</a></li>
+</ul>
+
+{{if .Disabled}}
+<p>Status: <b>disabled</b></p>
+{{end}}
+
+{{if .AllowDebug}}
+<p>Debug info at <a href='/debug/'>/debug/</a>.</p>
+{{end}}
+</body>
+</html>
+`))

cmd/derper/derper_test.go

@@ -4,6 +4,7 @@
 package main
 
 import (
+	"bytes"
 	"context"
 	"net/http"
 	"net/http/httptest"
@@ -107,6 +108,33 @@ func TestDeps(t *testing.T) {
 			"gvisor.dev/gvisor/pkg/tcpip/header": "https://github.com/tailscale/tailscale/issues/9756",
 			"tailscale.com/net/packet":           "not needed in derper",
 			"github.com/gaissmai/bart":           "not needed in derper",
+			"database/sql/driver":                "not needed in derper", // previously came in via github.com/google/uuid
 		},
 	}.Check(t)
 }
+
+func TestTemplate(t *testing.T) {
+	buf := &bytes.Buffer{}
+	err := homePageTemplate.Execute(buf, templateData{
+		ShowAbuseInfo: true,
+		Disabled:      true,
+		AllowDebug:    true,
+	})
+	if err != nil {
+		t.Fatal(err)
+	}
+
+	str := buf.String()
+	if !strings.Contains(str, "If you suspect abuse") {
+		t.Error("Output is missing abuse mailto")
+	}
+	if !strings.Contains(str, "Tailscale Security Policies") {
+		t.Error("Output is missing Tailscale Security Policies link")
+	}
+	if !strings.Contains(str, "Status:") {
+		t.Error("Output is missing disabled status")
+	}
+	if !strings.Contains(str, "Debug info") {
+		t.Error("Output is missing debug info")
+	}
+}

cmd/derper/mesh.go

@@ -10,7 +10,6 @@ import (
 	"log"
 	"net"
 	"strings"
-	"time"
 
 	"tailscale.com/derp"
 	"tailscale.com/derp/derphttp"
@@ -25,15 +24,28 @@ func startMesh(s *derp.Server) error {
 	if !s.HasMeshKey() {
 		return errors.New("--mesh-with requires --mesh-psk-file")
 	}
-	for _, host := range strings.Split(*meshWith, ",") {
-		if err := startMeshWithHost(s, host); err != nil {
+	for _, hostTuple := range strings.Split(*meshWith, ",") {
+		if err := startMeshWithHost(s, hostTuple); err != nil {
 			return err
 		}
 	}
 	return nil
 }
 
-func startMeshWithHost(s *derp.Server, host string) error {
+func startMeshWithHost(s *derp.Server, hostTuple string) error {
+	var host string
+	var dialHost string
+	hostParts := strings.Split(hostTuple, "/")
+	if len(hostParts) > 2 {
+		return fmt.Errorf("too many components in host tuple %q", hostTuple)
+	}
+	host = hostParts[0]
+	if len(hostParts) == 2 {
+		dialHost = hostParts[1]
+	} else {
+		dialHost = hostParts[0]
+	}
+
 	logf := logger.WithPrefix(log.Printf, fmt.Sprintf("mesh(%q): ", host))
 	netMon := netmon.NewStatic() // good enough for cmd/derper; no need for netns fanciness
 	c, err := derphttp.NewClient(s.PrivateKey(), "https://"+host+"/derp", logf, netMon)
@@ -43,31 +55,20 @@ func startMeshWithHost(s *derp.Server, host string) error {
 	c.MeshKey = s.MeshKey()
 	c.WatchConnectionChanges = true
 
-	// For meshed peers within a region, connect via VPC addresses.
-	c.SetURLDialer(func(ctx context.Context, network, addr string) (net.Conn, error) {
-		host, port, err := net.SplitHostPort(addr)
-		if err != nil {
-			return nil, err
-		}
+	logf("will dial %q for %q", dialHost, host)
+	if dialHost != host {
 		var d net.Dialer
-		var r net.Resolver
-		if base, ok := strings.CutSuffix(host, ".tailscale.com"); ok && port == "443" {
-			subCtx, cancel := context.WithTimeout(ctx, 2*time.Second)
-			defer cancel()
-			vpcHost := base + "-vpc.tailscale.com"
-			ips, _ := r.LookupIP(subCtx, "ip", vpcHost)
-			if len(ips) > 0 {
-				vpcAddr := net.JoinHostPort(ips[0].String(), port)
-				c, err := d.DialContext(subCtx, network, vpcAddr)
-				if err == nil {
-					log.Printf("connected to %v (%v) instead of %v", vpcHost, ips[0], base)
-					return c, nil
-				}
-				log.Printf("failed to connect to %v (%v): %v; trying non-VPC route", vpcHost, ips[0], err)
+		c.SetURLDialer(func(ctx context.Context, network, addr string) (net.Conn, error) {
+			_, port, err := net.SplitHostPort(addr)
+			if err != nil {
+				logf("failed to split %q: %v", addr, err)
+				return nil, err
 			}
-		}
-		return d.DialContext(ctx, network, addr)
-	})
+			dialAddr := net.JoinHostPort(dialHost, port)
+			logf("dialing %q instead of %q", dialAddr, addr)
+			return d.DialContext(ctx, network, dialAddr)
+		})
+	}
 
 	add := func(m derp.PeerPresentMessage) { s.AddPacketForwarder(m.Key, c) }
 	remove := func(m derp.PeerGoneMessage) { s.RemovePacketForwarder(m.Peer, c) }

cmd/derpprobe/derpprobe.go

@@ -18,17 +18,21 @@ import (
 )
 
 var (
-	derpMapURL   = flag.String("derp-map", "https://login.tailscale.com/derpmap/default", "URL to DERP map (https:// or file://) or 'local' to use the local tailscaled's DERP map")
-	versionFlag  = flag.Bool("version", false, "print version and exit")
-	listen       = flag.String("listen", ":8030", "HTTP listen address")
-	probeOnce    = flag.Bool("once", false, "probe once and print results, then exit; ignores the listen flag")
-	spread       = flag.Bool("spread", true, "whether to spread probing over time")
-	interval     = flag.Duration("interval", 15*time.Second, "probe interval")
-	meshInterval = flag.Duration("mesh-interval", 15*time.Second, "mesh probe interval")
-	stunInterval = flag.Duration("stun-interval", 15*time.Second, "STUN probe interval")
-	tlsInterval  = flag.Duration("tls-interval", 15*time.Second, "TLS probe interval")
-	bwInterval   = flag.Duration("bw-interval", 0, "bandwidth probe interval (0 = no bandwidth probing)")
-	bwSize       = flag.Int64("bw-probe-size-bytes", 1_000_000, "bandwidth probe size")
+	derpMapURL         = flag.String("derp-map", "https://login.tailscale.com/derpmap/default", "URL to DERP map (https:// or file://) or 'local' to use the local tailscaled's DERP map")
+	versionFlag        = flag.Bool("version", false, "print version and exit")
+	listen             = flag.String("listen", ":8030", "HTTP listen address")
+	probeOnce          = flag.Bool("once", false, "probe once and print results, then exit; ignores the listen flag")
+	spread             = flag.Bool("spread", true, "whether to spread probing over time")
+	interval           = flag.Duration("interval", 15*time.Second, "probe interval")
+	meshInterval       = flag.Duration("mesh-interval", 15*time.Second, "mesh probe interval")
+	stunInterval       = flag.Duration("stun-interval", 15*time.Second, "STUN probe interval")
+	tlsInterval        = flag.Duration("tls-interval", 15*time.Second, "TLS probe interval")
+	bwInterval         = flag.Duration("bw-interval", 0, "bandwidth probe interval (0 = no bandwidth probing)")
+	bwSize             = flag.Int64("bw-probe-size-bytes", 1_000_000, "bandwidth probe size")
+	bwTUNIPv4Address   = flag.String("bw-tun-ipv4-addr", "", "if specified, bandwidth probes will be performed over a TUN device at this address in order to exercise TCP-in-TCP in similar fashion to TCP over Tailscale via DERP; we will use a /30 subnet including this IP address")
+	qdPacketsPerSecond = flag.Int("qd-packets-per-second", 0, "if greater than 0, queuing delay will be measured continuously using 260 byte packets (approximate size of a CallMeMaybe packet) sent at this rate per second")
+	qdPacketTimeout    = flag.Duration("qd-packet-timeout", 5*time.Second, "queuing delay packets arriving after this period of time from being sent are treated like dropped packets and don't count toward queuing delay timings")
+	regionCodeOrID     = flag.String("region-code", "", "probe only this region (e.g. 'lax' or '17'); if left blank, all regions will be probed")
 )
 
 func main() {
@@ -43,9 +47,13 @@ func main() {
 		prober.WithMeshProbing(*meshInterval),
 		prober.WithSTUNProbing(*stunInterval),
 		prober.WithTLSProbing(*tlsInterval),
+		prober.WithQueuingDelayProbing(*qdPacketsPerSecond, *qdPacketTimeout),
 	}
 	if *bwInterval > 0 {
-		opts = append(opts, prober.WithBandwidthProbing(*bwInterval, *bwSize))
+		opts = append(opts, prober.WithBandwidthProbing(*bwInterval, *bwSize, *bwTUNIPv4Address))
+	}
+	if *regionCodeOrID != "" {
+		opts = append(opts, prober.WithRegionCodeOrID(*regionCodeOrID))
 	}
 	dp, err := prober.DERP(p, *derpMapURL, opts...)
 	if err != nil {
@@ -102,7 +110,7 @@ func getOverallStatus(p *prober.Prober) (o overallStatus) {
 			// Do not show probes that have not finished yet.
 			continue
 		}
-		if i.Result {
+		if i.Status == prober.ProbeStatusSucceeded {
 			o.addGoodf("%s: %s", p, i.Latency)
 		} else {
 			o.addBadf("%s: %s", p, i.Error)

cmd/get-authkey/main.go

@@ -46,7 +46,6 @@ func main() {
 		ClientID:     clientID,
 		ClientSecret: clientSecret,
 		TokenURL:     baseURL + "/api/v2/oauth/token",
-		Scopes:       []string{"device"},
 	}
 
 	ctx := context.Background()

cmd/gitops-pusher/gitops-pusher.go

@@ -58,8 +58,8 @@ func apply(cache *Cache, client *http.Client, tailnet, apiKey string) func(conte
 		}
 
 		if cache.PrevETag == "" {
-			log.Println("no previous etag found, assuming local file is correct and recording that")
-			cache.PrevETag = localEtag
+			log.Println("no previous etag found, assuming the latest control etag")
+			cache.PrevETag = controlEtag
 		}
 
 		log.Printf("control: %s", controlEtag)
@@ -105,8 +105,8 @@ func test(cache *Cache, client *http.Client, tailnet, apiKey string) func(contex
 		}
 
 		if cache.PrevETag == "" {
-			log.Println("no previous etag found, assuming local file is correct and recording that")
-			cache.PrevETag = localEtag
+			log.Println("no previous etag found, assuming the latest control etag")
+			cache.PrevETag = controlEtag
 		}
 
 		log.Printf("control: %s", controlEtag)
@@ -148,8 +148,8 @@ func getChecksums(cache *Cache, client *http.Client, tailnet, apiKey string) fun
 		}
 
 		if cache.PrevETag == "" {
-			log.Println("no previous etag found, assuming local file is correct and recording that")
-			cache.PrevETag = Shuck(localEtag)
+			log.Println("no previous etag found, assuming control etag")
+			cache.PrevETag = Shuck(controlEtag)
 		}
 
 		log.Printf("control: %s", controlEtag)

cmd/k8s-operator/connector.go

@@ -10,10 +10,12 @@ import (
 	"fmt"
 	"net/netip"
 	"slices"
+	"strings"
 	"sync"
 	"time"
 
-	"github.com/pkg/errors"
+	"errors"
+
 	"go.uber.org/zap"
 	xslices "golang.org/x/exp/slices"
 	corev1 "k8s.io/api/core/v1"
@@ -34,6 +36,7 @@ import (
 
 const (
 	reasonConnectorCreationFailed = "ConnectorCreationFailed"
+	reasonConnectorCreating       = "ConnectorCreating"
 	reasonConnectorCreated        = "ConnectorCreated"
 	reasonConnectorInvalid        = "ConnectorInvalid"
 
@@ -58,6 +61,7 @@ type ConnectorReconciler struct {
 
 	subnetRouters set.Slice[types.UID] // for subnet routers gauge
 	exitNodes     set.Slice[types.UID] // for exit nodes gauge
+	appConnectors set.Slice[types.UID] // for app connectors gauge
 }
 
 var (
@@ -67,6 +71,8 @@ var (
 	gaugeConnectorSubnetRouterResources = clientmetric.NewGauge(kubetypes.MetricConnectorWithSubnetRouterCount)
 	// gaugeConnectorExitNodeResources tracks the number of Connectors currently managed by this operator instance that are exit nodes.
 	gaugeConnectorExitNodeResources = clientmetric.NewGauge(kubetypes.MetricConnectorWithExitNodeCount)
+	// gaugeConnectorAppConnectorResources tracks the number of Connectors currently managed by this operator instance that are app connectors.
+	gaugeConnectorAppConnectorResources = clientmetric.NewGauge(kubetypes.MetricConnectorWithAppConnectorCount)
 )
 
 func (a *ConnectorReconciler) Reconcile(ctx context.Context, req reconcile.Request) (res reconcile.Result, err error) {
@@ -108,13 +114,12 @@ func (a *ConnectorReconciler) Reconcile(ctx context.Context, req reconcile.Reque
 	oldCnStatus := cn.Status.DeepCopy()
 	setStatus := func(cn *tsapi.Connector, _ tsapi.ConditionType, status metav1.ConditionStatus, reason, message string) (reconcile.Result, error) {
 		tsoperator.SetConnectorCondition(cn, tsapi.ConnectorReady, status, reason, message, cn.Generation, a.clock, logger)
-		if !apiequality.Semantic.DeepEqual(oldCnStatus, cn.Status) {
+		var updateErr error
+		if !apiequality.Semantic.DeepEqual(oldCnStatus, &cn.Status) {
 			// An error encountered here should get returned by the Reconcile function.
-			if updateErr := a.Client.Status().Update(ctx, cn); updateErr != nil {
-				err = errors.Wrap(err, updateErr.Error())
-			}
+			updateErr = a.Client.Status().Update(ctx, cn)
 		}
-		return res, err
+		return res, errors.Join(err, updateErr)
 	}
 
 	if !slices.Contains(cn.Finalizers, FinalizerName) {
@@ -131,17 +136,24 @@ func (a *ConnectorReconciler) Reconcile(ctx context.Context, req reconcile.Reque
 	}
 
 	if err := a.validate(cn); err != nil {
-		logger.Errorf("error validating Connector spec: %w", err)
 		message := fmt.Sprintf(messageConnectorInvalid, err)
 		a.recorder.Eventf(cn, corev1.EventTypeWarning, reasonConnectorInvalid, message)
 		return setStatus(cn, tsapi.ConnectorReady, metav1.ConditionFalse, reasonConnectorInvalid, message)
 	}
 
 	if err = a.maybeProvisionConnector(ctx, logger, cn); err != nil {
-		logger.Errorf("error creating Connector resources: %w", err)
+		reason := reasonConnectorCreationFailed
 		message := fmt.Sprintf(messageConnectorCreationFailed, err)
-		a.recorder.Eventf(cn, corev1.EventTypeWarning, reasonConnectorCreationFailed, message)
-		return setStatus(cn, tsapi.ConnectorReady, metav1.ConditionFalse, reasonConnectorCreationFailed, message)
+		if strings.Contains(err.Error(), optimisticLockErrorMsg) {
+			reason = reasonConnectorCreating
+			message = fmt.Sprintf("optimistic lock error, retrying: %s", err)
+			err = nil
+			logger.Info(message)
+		} else {
+			a.recorder.Eventf(cn, corev1.EventTypeWarning, reason, message)
+		}
+
+		return setStatus(cn, tsapi.ConnectorReady, metav1.ConditionFalse, reason, message)
 	}
 
 	logger.Info("Connector resources synced")
@@ -150,6 +162,9 @@ func (a *ConnectorReconciler) Reconcile(ctx context.Context, req reconcile.Reque
 		cn.Status.SubnetRoutes = cn.Spec.SubnetRouter.AdvertiseRoutes.Stringify()
 		return setStatus(cn, tsapi.ConnectorReady, metav1.ConditionTrue, reasonConnectorCreated, reasonConnectorCreated)
 	}
+	if cn.Spec.AppConnector != nil {
+		cn.Status.IsAppConnector = true
+	}
 	cn.Status.SubnetRoutes = ""
 	return setStatus(cn, tsapi.ConnectorReady, metav1.ConditionTrue, reasonConnectorCreated, reasonConnectorCreated)
 }
@@ -183,29 +198,44 @@ func (a *ConnectorReconciler) maybeProvisionConnector(ctx context.Context, logge
 			isExitNode: cn.Spec.ExitNode,
 		},
 		ProxyClassName: proxyClass,
+		proxyType:      proxyTypeConnector,
 	}
 
 	if cn.Spec.SubnetRouter != nil && len(cn.Spec.SubnetRouter.AdvertiseRoutes) > 0 {
 		sts.Connector.routes = cn.Spec.SubnetRouter.AdvertiseRoutes.Stringify()
 	}
 
+	if cn.Spec.AppConnector != nil {
+		sts.Connector.isAppConnector = true
+		if len(cn.Spec.AppConnector.Routes) != 0 {
+			sts.Connector.routes = cn.Spec.AppConnector.Routes.Stringify()
+		}
+	}
+
 	a.mu.Lock()
-	if sts.Connector.isExitNode {
+	if cn.Spec.ExitNode {
 		a.exitNodes.Add(cn.UID)
 	} else {
 		a.exitNodes.Remove(cn.UID)
 	}
-	if sts.Connector.routes != "" {
+	if cn.Spec.SubnetRouter != nil {
 		a.subnetRouters.Add(cn.GetUID())
 	} else {
 		a.subnetRouters.Remove(cn.GetUID())
 	}
+	if cn.Spec.AppConnector != nil {
+		a.appConnectors.Add(cn.GetUID())
+	} else {
+		a.appConnectors.Remove(cn.GetUID())
+	}
 	a.mu.Unlock()
 	gaugeConnectorSubnetRouterResources.Set(int64(a.subnetRouters.Len()))
 	gaugeConnectorExitNodeResources.Set(int64(a.exitNodes.Len()))
+	gaugeConnectorAppConnectorResources.Set(int64(a.appConnectors.Len()))
 	var connectors set.Slice[types.UID]
 	connectors.AddSlice(a.exitNodes.Slice())
 	connectors.AddSlice(a.subnetRouters.Slice())
+	connectors.AddSlice(a.appConnectors.Slice())
 	gaugeConnectorResources.Set(int64(connectors.Len()))
 
 	_, err := a.ssr.Provision(ctx, logger, sts)
@@ -213,27 +243,27 @@ func (a *ConnectorReconciler) maybeProvisionConnector(ctx context.Context, logge
 		return err
 	}
 
-	_, tsHost, ips, err := a.ssr.DeviceInfo(ctx, crl)
+	dev, err := a.ssr.DeviceInfo(ctx, crl, logger)
 	if err != nil {
 		return err
 	}
 
-	if tsHost == "" {
-		logger.Debugf("no Tailscale hostname known yet, waiting for connector pod to finish auth")
+	if dev == nil || dev.hostname == "" {
+		logger.Debugf("no Tailscale hostname known yet, waiting for Connector Pod to finish auth")
 		// No hostname yet. Wait for the connector pod to auth.
 		cn.Status.TailnetIPs = nil
 		cn.Status.Hostname = ""
 		return nil
 	}
 
-	cn.Status.TailnetIPs = ips
-	cn.Status.Hostname = tsHost
+	cn.Status.TailnetIPs = dev.ips
+	cn.Status.Hostname = dev.hostname
 
 	return nil
 }
 
 func (a *ConnectorReconciler) maybeCleanupConnector(ctx context.Context, logger *zap.SugaredLogger, cn *tsapi.Connector) (bool, error) {
-	if done, err := a.ssr.Cleanup(ctx, logger, childResourceLabels(cn.Name, a.tsnamespace, "connector")); err != nil {
+	if done, err := a.ssr.Cleanup(ctx, logger, childResourceLabels(cn.Name, a.tsnamespace, "connector"), proxyTypeConnector); err != nil {
 		return false, fmt.Errorf("failed to cleanup Connector resources: %w", err)
 	} else if !done {
 		logger.Debugf("Connector cleanup not done yet, waiting for next reconcile")
@@ -248,12 +278,15 @@ func (a *ConnectorReconciler) maybeCleanupConnector(ctx context.Context, logger
 	a.mu.Lock()
 	a.subnetRouters.Remove(cn.UID)
 	a.exitNodes.Remove(cn.UID)
+	a.appConnectors.Remove(cn.UID)
 	a.mu.Unlock()
 	gaugeConnectorExitNodeResources.Set(int64(a.exitNodes.Len()))
 	gaugeConnectorSubnetRouterResources.Set(int64(a.subnetRouters.Len()))
+	gaugeConnectorAppConnectorResources.Set(int64(a.appConnectors.Len()))
 	var connectors set.Slice[types.UID]
 	connectors.AddSlice(a.exitNodes.Slice())
 	connectors.AddSlice(a.subnetRouters.Slice())
+	connectors.AddSlice(a.appConnectors.Slice())
 	gaugeConnectorResources.Set(int64(connectors.Len()))
 	return true, nil
 }
@@ -262,8 +295,14 @@ func (a *ConnectorReconciler) validate(cn *tsapi.Connector) error {
 	// Connector fields are already validated at apply time with CEL validation
 	// on custom resource fields. The checks here are a backup in case the
 	// CEL validation breaks without us noticing.
-	if !(cn.Spec.SubnetRouter != nil || cn.Spec.ExitNode) {
-		return errors.New("invalid spec: a Connector must expose subnet routes or act as an exit node (or both)")
+	if cn.Spec.SubnetRouter == nil && !cn.Spec.ExitNode && cn.Spec.AppConnector == nil {
+		return errors.New("invalid spec: a Connector must be configured as at least one of subnet router, exit node or app connector")
+	}
+	if (cn.Spec.SubnetRouter != nil || cn.Spec.ExitNode) && cn.Spec.AppConnector != nil {
+		return errors.New("invalid spec: a Connector that is configured as an app connector must not be also configured as a subnet router or exit node")
+	}
+	if cn.Spec.AppConnector != nil {
+		return validateAppConnector(cn.Spec.AppConnector)
 	}
 	if cn.Spec.SubnetRouter == nil {
 		return nil
@@ -272,19 +311,27 @@ func (a *ConnectorReconciler) validate(cn *tsapi.Connector) error {
 }
 
 func validateSubnetRouter(sb *tsapi.SubnetRouter) error {
-	if len(sb.AdvertiseRoutes) < 1 {
+	if len(sb.AdvertiseRoutes) == 0 {
 		return errors.New("invalid subnet router spec: no routes defined")
 	}
-	var err error
-	for _, route := range sb.AdvertiseRoutes {
+	return validateRoutes(sb.AdvertiseRoutes)
+}
+
+func validateAppConnector(ac *tsapi.AppConnector) error {
+	return validateRoutes(ac.Routes)
+}
+
+func validateRoutes(routes tsapi.Routes) error {
+	var errs []error
+	for _, route := range routes {
 		pfx, e := netip.ParsePrefix(string(route))
 		if e != nil {
-			err = errors.Wrap(err, fmt.Sprintf("route %s is invalid: %v", route, err))
+			errs = append(errs, fmt.Errorf("route %v is invalid: %v", route, e))
 			continue
 		}
 		if pfx.Masked() != pfx {
-			err = errors.Wrap(err, fmt.Sprintf("route %s has non-address bits set; expected %s", pfx, pfx.Masked()))
+			errs = append(errs, fmt.Errorf("route %s has non-address bits set; expected %s", pfx, pfx.Masked()))
 		}
 	}
-	return err
+	return errors.Join(errs...)
 }

cmd/k8s-operator/connector_test.go

@@ -8,12 +8,14 @@ package main
 import (
 	"context"
 	"testing"
+	"time"
 
 	"go.uber.org/zap"
 	appsv1 "k8s.io/api/apps/v1"
 	corev1 "k8s.io/api/core/v1"
 	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
 	"k8s.io/apimachinery/pkg/types"
+	"k8s.io/client-go/tools/record"
 	"sigs.k8s.io/controller-runtime/pkg/client/fake"
 	tsapi "tailscale.com/k8s-operator/apis/v1alpha1"
 	"tailscale.com/kube/kubetypes"
@@ -77,8 +79,8 @@ func TestConnector(t *testing.T) {
 		subnetRoutes: "10.40.0.0/14",
 		app:          kubetypes.AppConnector,
 	}
-	expectEqual(t, fc, expectedSecret(t, fc, opts), nil)
-	expectEqual(t, fc, expectedSTS(t, fc, opts), removeHashAnnotation)
+	expectEqual(t, fc, expectedSecret(t, fc, opts))
+	expectEqual(t, fc, expectedSTS(t, fc, opts), removeHashAnnotation, removeResourceReqs)
 
 	// Connector status should get updated with the IP/hostname info when available.
 	const hostname = "foo.tailnetxyz.ts.net"
@@ -104,7 +106,7 @@ func TestConnector(t *testing.T) {
 	opts.subnetRoutes = "10.40.0.0/14,10.44.0.0/20"
 	expectReconciled(t, cr, "", "test")
 
-	expectEqual(t, fc, expectedSTS(t, fc, opts), removeHashAnnotation)
+	expectEqual(t, fc, expectedSTS(t, fc, opts), removeHashAnnotation, removeResourceReqs)
 
 	// Remove a route.
 	mustUpdate[tsapi.Connector](t, fc, "", "test", func(conn *tsapi.Connector) {
@@ -112,7 +114,7 @@ func TestConnector(t *testing.T) {
 	})
 	opts.subnetRoutes = "10.44.0.0/20"
 	expectReconciled(t, cr, "", "test")
-	expectEqual(t, fc, expectedSTS(t, fc, opts), removeHashAnnotation)
+	expectEqual(t, fc, expectedSTS(t, fc, opts), removeHashAnnotation, removeResourceReqs)
 
 	// Remove the subnet router.
 	mustUpdate[tsapi.Connector](t, fc, "", "test", func(conn *tsapi.Connector) {
@@ -120,7 +122,7 @@ func TestConnector(t *testing.T) {
 	})
 	opts.subnetRoutes = ""
 	expectReconciled(t, cr, "", "test")
-	expectEqual(t, fc, expectedSTS(t, fc, opts), removeHashAnnotation)
+	expectEqual(t, fc, expectedSTS(t, fc, opts), removeHashAnnotation, removeResourceReqs)
 
 	// Re-add the subnet router.
 	mustUpdate[tsapi.Connector](t, fc, "", "test", func(conn *tsapi.Connector) {
@@ -130,7 +132,7 @@ func TestConnector(t *testing.T) {
 	})
 	opts.subnetRoutes = "10.44.0.0/20"
 	expectReconciled(t, cr, "", "test")
-	expectEqual(t, fc, expectedSTS(t, fc, opts), removeHashAnnotation)
+	expectEqual(t, fc, expectedSTS(t, fc, opts), removeHashAnnotation, removeResourceReqs)
 
 	// Delete the Connector.
 	if err = fc.Delete(context.Background(), cn); err != nil {
@@ -173,8 +175,8 @@ func TestConnector(t *testing.T) {
 		hostname:     "test-connector",
 		app:          kubetypes.AppConnector,
 	}
-	expectEqual(t, fc, expectedSecret(t, fc, opts), nil)
-	expectEqual(t, fc, expectedSTS(t, fc, opts), removeHashAnnotation)
+	expectEqual(t, fc, expectedSecret(t, fc, opts))
+	expectEqual(t, fc, expectedSTS(t, fc, opts), removeHashAnnotation, removeResourceReqs)
 
 	// Add an exit node.
 	mustUpdate[tsapi.Connector](t, fc, "", "test", func(conn *tsapi.Connector) {
@@ -182,7 +184,7 @@ func TestConnector(t *testing.T) {
 	})
 	opts.isExitNode = true
 	expectReconciled(t, cr, "", "test")
-	expectEqual(t, fc, expectedSTS(t, fc, opts), removeHashAnnotation)
+	expectEqual(t, fc, expectedSTS(t, fc, opts), removeHashAnnotation, removeResourceReqs)
 
 	// Delete the Connector.
 	if err = fc.Delete(context.Background(), cn); err != nil {
@@ -201,7 +203,7 @@ func TestConnectorWithProxyClass(t *testing.T) {
 	pc := &tsapi.ProxyClass{
 		ObjectMeta: metav1.ObjectMeta{Name: "custom-metadata"},
 		Spec: tsapi.ProxyClassSpec{StatefulSet: &tsapi.StatefulSet{
-			Labels:      map[string]string{"foo": "bar"},
+			Labels:      tsapi.Labels{"foo": "bar"},
 			Annotations: map[string]string{"bar.io/foo": "some-val"},
 			Pod:         &tsapi.Pod{Annotations: map[string]string{"foo.io/bar": "some-val"}}}},
 	}
@@ -259,8 +261,8 @@ func TestConnectorWithProxyClass(t *testing.T) {
 		subnetRoutes: "10.40.0.0/14",
 		app:          kubetypes.AppConnector,
 	}
-	expectEqual(t, fc, expectedSecret(t, fc, opts), nil)
-	expectEqual(t, fc, expectedSTS(t, fc, opts), removeHashAnnotation)
+	expectEqual(t, fc, expectedSecret(t, fc, opts))
+	expectEqual(t, fc, expectedSTS(t, fc, opts), removeHashAnnotation, removeResourceReqs)
 
 	// 2. Update Connector to specify a ProxyClass. ProxyClass is not yet
 	// ready, so its configuration is NOT applied to the Connector
@@ -269,7 +271,7 @@ func TestConnectorWithProxyClass(t *testing.T) {
 		conn.Spec.ProxyClass = "custom-metadata"
 	})
 	expectReconciled(t, cr, "", "test")
-	expectEqual(t, fc, expectedSTS(t, fc, opts), removeHashAnnotation)
+	expectEqual(t, fc, expectedSTS(t, fc, opts), removeHashAnnotation, removeResourceReqs)
 
 	// 3. ProxyClass is set to Ready by proxy-class reconciler. Connector
 	// get reconciled and configuration from the ProxyClass is applied to
@@ -284,7 +286,7 @@ func TestConnectorWithProxyClass(t *testing.T) {
 	})
 	opts.proxyClass = pc.Name
 	expectReconciled(t, cr, "", "test")
-	expectEqual(t, fc, expectedSTS(t, fc, opts), removeHashAnnotation)
+	expectEqual(t, fc, expectedSTS(t, fc, opts), removeHashAnnotation, removeResourceReqs)
 
 	// 4. Connector.spec.proxyClass field is unset, Connector gets
 	// reconciled and configuration from the ProxyClass is removed from the
@@ -294,5 +296,102 @@ func TestConnectorWithProxyClass(t *testing.T) {
 	})
 	opts.proxyClass = ""
 	expectReconciled(t, cr, "", "test")
-	expectEqual(t, fc, expectedSTS(t, fc, opts), removeHashAnnotation)
+	expectEqual(t, fc, expectedSTS(t, fc, opts), removeHashAnnotation, removeResourceReqs)
+}
+
+func TestConnectorWithAppConnector(t *testing.T) {
+	// Setup
+	cn := &tsapi.Connector{
+		ObjectMeta: metav1.ObjectMeta{
+			Name: "test",
+			UID:  types.UID("1234-UID"),
+		},
+		TypeMeta: metav1.TypeMeta{
+			Kind:       tsapi.ConnectorKind,
+			APIVersion: "tailscale.io/v1alpha1",
+		},
+		Spec: tsapi.ConnectorSpec{
+			AppConnector: &tsapi.AppConnector{},
+		},
+	}
+	fc := fake.NewClientBuilder().
+		WithScheme(tsapi.GlobalScheme).
+		WithObjects(cn).
+		WithStatusSubresource(cn).
+		Build()
+	ft := &fakeTSClient{}
+	zl, err := zap.NewDevelopment()
+	if err != nil {
+		t.Fatal(err)
+	}
+	cl := tstest.NewClock(tstest.ClockOpts{})
+	fr := record.NewFakeRecorder(1)
+	cr := &ConnectorReconciler{
+		Client: fc,
+		clock:  cl,
+		ssr: &tailscaleSTSReconciler{
+			Client:            fc,
+			tsClient:          ft,
+			defaultTags:       []string{"tag:k8s"},
+			operatorNamespace: "operator-ns",
+			proxyImage:        "tailscale/tailscale",
+		},
+		logger:   zl.Sugar(),
+		recorder: fr,
+	}
+
+	// 1. Connector with app connnector is created and becomes ready
+	expectReconciled(t, cr, "", "test")
+	fullName, shortName := findGenName(t, fc, "", "test", "connector")
+	opts := configOpts{
+		stsName:        shortName,
+		secretName:     fullName,
+		parentType:     "connector",
+		hostname:       "test-connector",
+		app:            kubetypes.AppConnector,
+		isAppConnector: true,
+	}
+	expectEqual(t, fc, expectedSecret(t, fc, opts))
+	expectEqual(t, fc, expectedSTS(t, fc, opts), removeHashAnnotation, removeResourceReqs)
+	// Connector's ready condition should be set to true
+
+	cn.ObjectMeta.Finalizers = append(cn.ObjectMeta.Finalizers, "tailscale.com/finalizer")
+	cn.Status.IsAppConnector = true
+	cn.Status.Conditions = []metav1.Condition{{
+		Type:               string(tsapi.ConnectorReady),
+		Status:             metav1.ConditionTrue,
+		LastTransitionTime: metav1.Time{Time: cl.Now().Truncate(time.Second)},
+		Reason:             reasonConnectorCreated,
+		Message:            reasonConnectorCreated,
+	}}
+	expectEqual(t, fc, cn)
+
+	// 2. Connector with invalid app connector routes has status set to invalid
+	mustUpdate[tsapi.Connector](t, fc, "", "test", func(conn *tsapi.Connector) {
+		conn.Spec.AppConnector.Routes = tsapi.Routes{tsapi.Route("1.2.3.4/5")}
+	})
+	cn.Spec.AppConnector.Routes = tsapi.Routes{tsapi.Route("1.2.3.4/5")}
+	expectReconciled(t, cr, "", "test")
+	cn.Status.Conditions = []metav1.Condition{{
+		Type:               string(tsapi.ConnectorReady),
+		Status:             metav1.ConditionFalse,
+		LastTransitionTime: metav1.Time{Time: cl.Now().Truncate(time.Second)},
+		Reason:             reasonConnectorInvalid,
+		Message:            "Connector is invalid: route 1.2.3.4/5 has non-address bits set; expected 0.0.0.0/5",
+	}}
+	expectEqual(t, fc, cn)
+
+	// 3. Connector with valid app connnector routes becomes ready
+	mustUpdate[tsapi.Connector](t, fc, "", "test", func(conn *tsapi.Connector) {
+		conn.Spec.AppConnector.Routes = tsapi.Routes{tsapi.Route("10.88.2.21/32")}
+	})
+	cn.Spec.AppConnector.Routes = tsapi.Routes{tsapi.Route("10.88.2.21/32")}
+	cn.Status.Conditions = []metav1.Condition{{
+		Type:               string(tsapi.ConnectorReady),
+		Status:             metav1.ConditionTrue,
+		LastTransitionTime: metav1.Time{Time: cl.Now().Truncate(time.Second)},
+		Reason:             reasonConnectorCreated,
+		Message:            reasonConnectorCreated,
+	}}
+	expectReconciled(t, cr, "", "test")
 }

cmd/k8s-operator/depaware.txt

@@ -80,10 +80,6 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
         github.com/beorn7/perks/quantile                             from github.com/prometheus/client_golang/prometheus
         github.com/bits-and-blooms/bitset                            from github.com/gaissmai/bart
      💣 github.com/cespare/xxhash/v2                                 from github.com/prometheus/client_golang/prometheus
-        github.com/coder/websocket                                   from tailscale.com/control/controlhttp+
-        github.com/coder/websocket/internal/errd                     from github.com/coder/websocket
-        github.com/coder/websocket/internal/util                     from github.com/coder/websocket
-        github.com/coder/websocket/internal/xsync                    from github.com/coder/websocket
    L    github.com/coreos/go-iptables/iptables                       from tailscale.com/util/linuxfw
      💣 github.com/davecgh/go-spew/spew                              from k8s.io/apimachinery/pkg/util/dump
    W 💣 github.com/dblohm7/wingoes                                   from github.com/dblohm7/wingoes/com+
@@ -98,7 +94,7 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
         github.com/evanphx/json-patch/v5                             from sigs.k8s.io/controller-runtime/pkg/client
         github.com/evanphx/json-patch/v5/internal/json               from github.com/evanphx/json-patch/v5
      💣 github.com/fsnotify/fsnotify                                 from sigs.k8s.io/controller-runtime/pkg/certwatcher
-        github.com/fxamacker/cbor/v2                                 from tailscale.com/tka
+        github.com/fxamacker/cbor/v2                                 from tailscale.com/tka+
         github.com/gaissmai/bart                                     from tailscale.com/net/ipset+
         github.com/go-json-experiment/json                           from tailscale.com/types/opt+
         github.com/go-json-experiment/json/internal                  from github.com/go-json-experiment/json/internal/jsonflags+
@@ -114,11 +110,11 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
         github.com/go-openapi/jsonpointer                            from github.com/go-openapi/jsonreference
         github.com/go-openapi/jsonreference                          from k8s.io/kube-openapi/pkg/internal+
         github.com/go-openapi/jsonreference/internal                 from github.com/go-openapi/jsonreference
-        github.com/go-openapi/swag                                   from github.com/go-openapi/jsonpointer+
+     💣 github.com/go-openapi/swag                                   from github.com/go-openapi/jsonpointer+
    L 💣 github.com/godbus/dbus/v5                                    from tailscale.com/net/dns
      💣 github.com/gogo/protobuf/proto                               from k8s.io/api/admission/v1+
         github.com/gogo/protobuf/sortkeys                            from k8s.io/api/admission/v1+
-        github.com/golang/groupcache/lru                             from k8s.io/client-go/tools/record+
+        github.com/golang/groupcache/lru                             from tailscale.com/net/dnscache
         github.com/golang/protobuf/proto                             from k8s.io/client-go/discovery+
         github.com/google/btree                                      from gvisor.dev/gvisor/pkg/tcpip/header+
         github.com/google/gnostic-models/compiler                    from github.com/google/gnostic-models/openapiv2+
@@ -144,14 +140,12 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
         github.com/gorilla/securecookie                              from github.com/gorilla/csrf
         github.com/hdevalence/ed25519consensus                       from tailscale.com/clientupdate/distsign+
    L 💣 github.com/illarion/gonotify/v2                              from tailscale.com/net/dns
-        github.com/imdario/mergo                                     from k8s.io/client-go/tools/clientcmd
-   L    github.com/insomniacslk/dhcp/dhcpv4                          from tailscale.com/net/tstun
+   L    github.com/insomniacslk/dhcp/dhcpv4                          from tailscale.com/feature/tap
    L    github.com/insomniacslk/dhcp/iana                            from github.com/insomniacslk/dhcp/dhcpv4
    L    github.com/insomniacslk/dhcp/interfaces                      from github.com/insomniacslk/dhcp/dhcpv4
    L    github.com/insomniacslk/dhcp/rfc1035label                    from github.com/insomniacslk/dhcp/dhcpv4
    L    github.com/jmespath/go-jmespath                              from github.com/aws/aws-sdk-go-v2/service/ssm
         github.com/josharian/intern                                  from github.com/mailru/easyjson/jlexer
-   L    github.com/josharian/native                                  from github.com/mdlayher/netlink+
    L 💣 github.com/jsimonetti/rtnetlink                              from tailscale.com/net/netmon
    L    github.com/jsimonetti/rtnetlink/internal/unix                from github.com/jsimonetti/rtnetlink
      💣 github.com/json-iterator/go                                  from sigs.k8s.io/structured-merge-diff/v4/fieldpath+
@@ -162,7 +156,7 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
         github.com/klauspost/compress/internal/snapref               from github.com/klauspost/compress/zstd
         github.com/klauspost/compress/zstd                           from tailscale.com/util/zstdframe
         github.com/klauspost/compress/zstd/internal/xxhash           from github.com/klauspost/compress/zstd
-        github.com/kortschak/wol                                     from tailscale.com/ipn/ipnlocal
+        github.com/kortschak/wol                                     from tailscale.com/feature/wakeonlan
         github.com/mailru/easyjson/buffer                            from github.com/mailru/easyjson/jwriter
      💣 github.com/mailru/easyjson/jlexer                            from github.com/go-openapi/swag
         github.com/mailru/easyjson/jwriter                           from github.com/go-openapi/swag
@@ -176,7 +170,7 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
      💣 github.com/mitchellh/go-ps                                   from tailscale.com/safesocket
         github.com/modern-go/concurrent                              from github.com/json-iterator/go
      💣 github.com/modern-go/reflect2                                from github.com/json-iterator/go
-        github.com/munnerz/goautoneg                                 from k8s.io/kube-openapi/pkg/handler3
+        github.com/munnerz/goautoneg                                 from k8s.io/kube-openapi/pkg/handler3+
         github.com/opencontainers/go-digest                          from github.com/distribution/reference
    L    github.com/pierrec/lz4/v4                                    from github.com/u-root/uio/uio
    L    github.com/pierrec/lz4/v4/internal/lz4block                  from github.com/pierrec/lz4/v4+
@@ -191,7 +185,6 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
         github.com/prometheus/client_golang/prometheus/promhttp      from sigs.k8s.io/controller-runtime/pkg/metrics/server+
         github.com/prometheus/client_model/go                        from github.com/prometheus/client_golang/prometheus+
         github.com/prometheus/common/expfmt                          from github.com/prometheus/client_golang/prometheus+
-        github.com/prometheus/common/internal/bitbucket.org/ww/goautoneg from github.com/prometheus/common/expfmt
         github.com/prometheus/common/model                           from github.com/prometheus/client_golang/prometheus+
   LD    github.com/prometheus/procfs                                 from github.com/prometheus/client_golang/prometheus
   LD    github.com/prometheus/procfs/internal/fs                     from github.com/prometheus/procfs
@@ -229,7 +222,6 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
         github.com/tailscale/wireguard-go/rwcancel                   from github.com/tailscale/wireguard-go/device+
         github.com/tailscale/wireguard-go/tai64n                     from github.com/tailscale/wireguard-go/device
      💣 github.com/tailscale/wireguard-go/tun                        from github.com/tailscale/wireguard-go/device+
-        github.com/tcnksm/go-httpstat                                from tailscale.com/net/netcheck
    L    github.com/u-root/uio/rand                                   from github.com/insomniacslk/dhcp/dhcpv4
    L    github.com/u-root/uio/uio                                    from github.com/insomniacslk/dhcp/dhcpv4+
    L    github.com/vishvananda/netns                                 from github.com/tailscale/netlink+
@@ -256,6 +248,7 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
         google.golang.org/protobuf/internal/descopts                 from google.golang.org/protobuf/internal/filedesc+
         google.golang.org/protobuf/internal/detrand                  from google.golang.org/protobuf/internal/descfmt+
         google.golang.org/protobuf/internal/editiondefaults          from google.golang.org/protobuf/internal/filedesc+
+        google.golang.org/protobuf/internal/editionssupport          from google.golang.org/protobuf/reflect/protodesc
         google.golang.org/protobuf/internal/encoding/defval          from google.golang.org/protobuf/internal/encoding/tag+
         google.golang.org/protobuf/internal/encoding/messageset      from google.golang.org/protobuf/encoding/prototext+
         google.golang.org/protobuf/internal/encoding/tag             from google.golang.org/protobuf/internal/impl
@@ -281,8 +274,8 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
         google.golang.org/protobuf/types/gofeaturespb                from google.golang.org/protobuf/reflect/protodesc
         google.golang.org/protobuf/types/known/anypb                 from github.com/google/gnostic-models/compiler+
         google.golang.org/protobuf/types/known/timestamppb           from github.com/prometheus/client_golang/prometheus+
+        gopkg.in/evanphx/json-patch.v4                               from k8s.io/client-go/testing
         gopkg.in/inf.v0                                              from k8s.io/apimachinery/pkg/api/resource
-        gopkg.in/yaml.v2                                             from k8s.io/kube-openapi/pkg/util/proto+
         gopkg.in/yaml.v3                                             from github.com/go-openapi/swag+
         gvisor.dev/gvisor/pkg/atomicbitops                           from gvisor.dev/gvisor/pkg/buffer+
         gvisor.dev/gvisor/pkg/bits                                   from gvisor.dev/gvisor/pkg/buffer
@@ -309,7 +302,7 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
         gvisor.dev/gvisor/pkg/tcpip/network/internal/fragmentation   from gvisor.dev/gvisor/pkg/tcpip/network/ipv4+
         gvisor.dev/gvisor/pkg/tcpip/network/internal/ip              from gvisor.dev/gvisor/pkg/tcpip/network/ipv4+
         gvisor.dev/gvisor/pkg/tcpip/network/internal/multicast       from gvisor.dev/gvisor/pkg/tcpip/network/ipv4+
-        gvisor.dev/gvisor/pkg/tcpip/network/ipv4                     from tailscale.com/net/tstun+
+        gvisor.dev/gvisor/pkg/tcpip/network/ipv4                     from tailscale.com/feature/tap+
         gvisor.dev/gvisor/pkg/tcpip/network/ipv6                     from tailscale.com/wgengine/netstack+
         gvisor.dev/gvisor/pkg/tcpip/ports                            from gvisor.dev/gvisor/pkg/tcpip/stack+
         gvisor.dev/gvisor/pkg/tcpip/seqnum                           from gvisor.dev/gvisor/pkg/tcpip/header+
@@ -351,6 +344,7 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
         k8s.io/api/certificates/v1alpha1                             from k8s.io/client-go/applyconfigurations/certificates/v1alpha1+
         k8s.io/api/certificates/v1beta1                              from k8s.io/client-go/applyconfigurations/certificates/v1beta1+
         k8s.io/api/coordination/v1                                   from k8s.io/client-go/applyconfigurations/coordination/v1+
+        k8s.io/api/coordination/v1alpha2                             from k8s.io/client-go/applyconfigurations/coordination/v1alpha2+
         k8s.io/api/coordination/v1beta1                              from k8s.io/client-go/applyconfigurations/coordination/v1beta1+
         k8s.io/api/core/v1                                           from k8s.io/api/apps/v1+
         k8s.io/api/discovery/v1                                      from k8s.io/client-go/applyconfigurations/discovery/v1+
@@ -373,7 +367,8 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
         k8s.io/api/rbac/v1                                           from k8s.io/client-go/applyconfigurations/rbac/v1+
         k8s.io/api/rbac/v1alpha1                                     from k8s.io/client-go/applyconfigurations/rbac/v1alpha1+
         k8s.io/api/rbac/v1beta1                                      from k8s.io/client-go/applyconfigurations/rbac/v1beta1+
-        k8s.io/api/resource/v1alpha2                                 from k8s.io/client-go/applyconfigurations/resource/v1alpha2+
+        k8s.io/api/resource/v1alpha3                                 from k8s.io/client-go/applyconfigurations/resource/v1alpha3+
+        k8s.io/api/resource/v1beta1                                  from k8s.io/client-go/applyconfigurations/resource/v1beta1+
         k8s.io/api/scheduling/v1                                     from k8s.io/client-go/applyconfigurations/scheduling/v1+
         k8s.io/api/scheduling/v1alpha1                               from k8s.io/client-go/applyconfigurations/scheduling/v1alpha1+
         k8s.io/api/scheduling/v1beta1                                from k8s.io/client-go/applyconfigurations/scheduling/v1beta1+
@@ -382,14 +377,16 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
         k8s.io/api/storage/v1beta1                                   from k8s.io/client-go/applyconfigurations/storage/v1beta1+
         k8s.io/api/storagemigration/v1alpha1                         from k8s.io/client-go/applyconfigurations/storagemigration/v1alpha1+
         k8s.io/apiextensions-apiserver/pkg/apis/apiextensions        from k8s.io/apiextensions-apiserver/pkg/apis/apiextensions/v1
-     💣 k8s.io/apiextensions-apiserver/pkg/apis/apiextensions/v1     from sigs.k8s.io/controller-runtime/pkg/webhook/conversion
+     💣 k8s.io/apiextensions-apiserver/pkg/apis/apiextensions/v1     from sigs.k8s.io/controller-runtime/pkg/webhook/conversion+
         k8s.io/apimachinery/pkg/api/equality                         from k8s.io/apiextensions-apiserver/pkg/apis/apiextensions/v1+
         k8s.io/apimachinery/pkg/api/errors                           from k8s.io/apimachinery/pkg/util/managedfields/internal+
         k8s.io/apimachinery/pkg/api/meta                             from k8s.io/apimachinery/pkg/api/validation+
+        k8s.io/apimachinery/pkg/api/meta/testrestmapper              from k8s.io/client-go/testing
         k8s.io/apimachinery/pkg/api/resource                         from k8s.io/api/autoscaling/v1+
         k8s.io/apimachinery/pkg/api/validation                       from k8s.io/apimachinery/pkg/util/managedfields/internal+
      💣 k8s.io/apimachinery/pkg/apis/meta/internalversion            from k8s.io/apimachinery/pkg/apis/meta/internalversion/scheme+
         k8s.io/apimachinery/pkg/apis/meta/internalversion/scheme     from k8s.io/client-go/metadata
+        k8s.io/apimachinery/pkg/apis/meta/internalversion/validation from k8s.io/client-go/util/watchlist
      💣 k8s.io/apimachinery/pkg/apis/meta/v1                         from k8s.io/api/admission/v1+
         k8s.io/apimachinery/pkg/apis/meta/v1/unstructured            from k8s.io/apimachinery/pkg/runtime/serializer/versioning+
         k8s.io/apimachinery/pkg/apis/meta/v1/validation              from k8s.io/apimachinery/pkg/api/validation+
@@ -401,6 +398,9 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
         k8s.io/apimachinery/pkg/runtime                              from k8s.io/api/admission/v1+
         k8s.io/apimachinery/pkg/runtime/schema                       from k8s.io/api/admission/v1+
         k8s.io/apimachinery/pkg/runtime/serializer                   from k8s.io/apimachinery/pkg/apis/meta/internalversion/scheme+
+        k8s.io/apimachinery/pkg/runtime/serializer/cbor              from k8s.io/client-go/dynamic+
+        k8s.io/apimachinery/pkg/runtime/serializer/cbor/direct       from k8s.io/apiextensions-apiserver/pkg/apis/apiextensions/v1+
+        k8s.io/apimachinery/pkg/runtime/serializer/cbor/internal/modes from k8s.io/apimachinery/pkg/runtime/serializer/cbor+
         k8s.io/apimachinery/pkg/runtime/serializer/json              from k8s.io/apimachinery/pkg/runtime/serializer+
         k8s.io/apimachinery/pkg/runtime/serializer/protobuf          from k8s.io/apimachinery/pkg/runtime/serializer
         k8s.io/apimachinery/pkg/runtime/serializer/recognizer        from k8s.io/apimachinery/pkg/runtime/serializer+
@@ -452,6 +452,7 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
         k8s.io/client-go/applyconfigurations/certificates/v1alpha1   from k8s.io/client-go/kubernetes/typed/certificates/v1alpha1
         k8s.io/client-go/applyconfigurations/certificates/v1beta1    from k8s.io/client-go/kubernetes/typed/certificates/v1beta1
         k8s.io/client-go/applyconfigurations/coordination/v1         from k8s.io/client-go/kubernetes/typed/coordination/v1
+        k8s.io/client-go/applyconfigurations/coordination/v1alpha2   from k8s.io/client-go/kubernetes/typed/coordination/v1alpha2
         k8s.io/client-go/applyconfigurations/coordination/v1beta1    from k8s.io/client-go/kubernetes/typed/coordination/v1beta1
         k8s.io/client-go/applyconfigurations/core/v1                 from k8s.io/client-go/applyconfigurations/apps/v1+
         k8s.io/client-go/applyconfigurations/discovery/v1            from k8s.io/client-go/kubernetes/typed/discovery/v1
@@ -476,7 +477,8 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
         k8s.io/client-go/applyconfigurations/rbac/v1                 from k8s.io/client-go/kubernetes/typed/rbac/v1
         k8s.io/client-go/applyconfigurations/rbac/v1alpha1           from k8s.io/client-go/kubernetes/typed/rbac/v1alpha1
         k8s.io/client-go/applyconfigurations/rbac/v1beta1            from k8s.io/client-go/kubernetes/typed/rbac/v1beta1
-        k8s.io/client-go/applyconfigurations/resource/v1alpha2       from k8s.io/client-go/kubernetes/typed/resource/v1alpha2
+        k8s.io/client-go/applyconfigurations/resource/v1alpha3       from k8s.io/client-go/kubernetes/typed/resource/v1alpha3
+        k8s.io/client-go/applyconfigurations/resource/v1beta1        from k8s.io/client-go/kubernetes/typed/resource/v1beta1
         k8s.io/client-go/applyconfigurations/scheduling/v1           from k8s.io/client-go/kubernetes/typed/scheduling/v1
         k8s.io/client-go/applyconfigurations/scheduling/v1alpha1     from k8s.io/client-go/kubernetes/typed/scheduling/v1alpha1
         k8s.io/client-go/applyconfigurations/scheduling/v1beta1      from k8s.io/client-go/kubernetes/typed/scheduling/v1beta1
@@ -486,8 +488,80 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
         k8s.io/client-go/applyconfigurations/storagemigration/v1alpha1 from k8s.io/client-go/kubernetes/typed/storagemigration/v1alpha1
         k8s.io/client-go/discovery                                   from k8s.io/client-go/applyconfigurations/meta/v1+
         k8s.io/client-go/dynamic                                     from sigs.k8s.io/controller-runtime/pkg/cache/internal+
-        k8s.io/client-go/features                                    from k8s.io/client-go/tools/cache
-        k8s.io/client-go/kubernetes                                  from k8s.io/client-go/tools/leaderelection/resourcelock
+        k8s.io/client-go/features                                    from k8s.io/client-go/tools/cache+
+        k8s.io/client-go/gentype                                     from k8s.io/client-go/kubernetes/typed/admissionregistration/v1+
+        k8s.io/client-go/informers                                   from k8s.io/client-go/tools/leaderelection
+        k8s.io/client-go/informers/admissionregistration             from k8s.io/client-go/informers
+        k8s.io/client-go/informers/admissionregistration/v1          from k8s.io/client-go/informers/admissionregistration
+        k8s.io/client-go/informers/admissionregistration/v1alpha1    from k8s.io/client-go/informers/admissionregistration
+        k8s.io/client-go/informers/admissionregistration/v1beta1     from k8s.io/client-go/informers/admissionregistration
+        k8s.io/client-go/informers/apiserverinternal                 from k8s.io/client-go/informers
+        k8s.io/client-go/informers/apiserverinternal/v1alpha1        from k8s.io/client-go/informers/apiserverinternal
+        k8s.io/client-go/informers/apps                              from k8s.io/client-go/informers
+        k8s.io/client-go/informers/apps/v1                           from k8s.io/client-go/informers/apps
+        k8s.io/client-go/informers/apps/v1beta1                      from k8s.io/client-go/informers/apps
+        k8s.io/client-go/informers/apps/v1beta2                      from k8s.io/client-go/informers/apps
+        k8s.io/client-go/informers/autoscaling                       from k8s.io/client-go/informers
+        k8s.io/client-go/informers/autoscaling/v1                    from k8s.io/client-go/informers/autoscaling
+        k8s.io/client-go/informers/autoscaling/v2                    from k8s.io/client-go/informers/autoscaling
+        k8s.io/client-go/informers/autoscaling/v2beta1               from k8s.io/client-go/informers/autoscaling
+        k8s.io/client-go/informers/autoscaling/v2beta2               from k8s.io/client-go/informers/autoscaling
+        k8s.io/client-go/informers/batch                             from k8s.io/client-go/informers
+        k8s.io/client-go/informers/batch/v1                          from k8s.io/client-go/informers/batch
+        k8s.io/client-go/informers/batch/v1beta1                     from k8s.io/client-go/informers/batch
+        k8s.io/client-go/informers/certificates                      from k8s.io/client-go/informers
+        k8s.io/client-go/informers/certificates/v1                   from k8s.io/client-go/informers/certificates
+        k8s.io/client-go/informers/certificates/v1alpha1             from k8s.io/client-go/informers/certificates
+        k8s.io/client-go/informers/certificates/v1beta1              from k8s.io/client-go/informers/certificates
+        k8s.io/client-go/informers/coordination                      from k8s.io/client-go/informers
+        k8s.io/client-go/informers/coordination/v1                   from k8s.io/client-go/informers/coordination
+        k8s.io/client-go/informers/coordination/v1alpha2             from k8s.io/client-go/informers/coordination
+        k8s.io/client-go/informers/coordination/v1beta1              from k8s.io/client-go/informers/coordination
+        k8s.io/client-go/informers/core                              from k8s.io/client-go/informers
+        k8s.io/client-go/informers/core/v1                           from k8s.io/client-go/informers/core
+        k8s.io/client-go/informers/discovery                         from k8s.io/client-go/informers
+        k8s.io/client-go/informers/discovery/v1                      from k8s.io/client-go/informers/discovery
+        k8s.io/client-go/informers/discovery/v1beta1                 from k8s.io/client-go/informers/discovery
+        k8s.io/client-go/informers/events                            from k8s.io/client-go/informers
+        k8s.io/client-go/informers/events/v1                         from k8s.io/client-go/informers/events
+        k8s.io/client-go/informers/events/v1beta1                    from k8s.io/client-go/informers/events
+        k8s.io/client-go/informers/extensions                        from k8s.io/client-go/informers
+        k8s.io/client-go/informers/extensions/v1beta1                from k8s.io/client-go/informers/extensions
+        k8s.io/client-go/informers/flowcontrol                       from k8s.io/client-go/informers
+        k8s.io/client-go/informers/flowcontrol/v1                    from k8s.io/client-go/informers/flowcontrol
+        k8s.io/client-go/informers/flowcontrol/v1beta1               from k8s.io/client-go/informers/flowcontrol
+        k8s.io/client-go/informers/flowcontrol/v1beta2               from k8s.io/client-go/informers/flowcontrol
+        k8s.io/client-go/informers/flowcontrol/v1beta3               from k8s.io/client-go/informers/flowcontrol
+        k8s.io/client-go/informers/internalinterfaces                from k8s.io/client-go/informers+
+        k8s.io/client-go/informers/networking                        from k8s.io/client-go/informers
+        k8s.io/client-go/informers/networking/v1                     from k8s.io/client-go/informers/networking
+        k8s.io/client-go/informers/networking/v1alpha1               from k8s.io/client-go/informers/networking
+        k8s.io/client-go/informers/networking/v1beta1                from k8s.io/client-go/informers/networking
+        k8s.io/client-go/informers/node                              from k8s.io/client-go/informers
+        k8s.io/client-go/informers/node/v1                           from k8s.io/client-go/informers/node
+        k8s.io/client-go/informers/node/v1alpha1                     from k8s.io/client-go/informers/node
+        k8s.io/client-go/informers/node/v1beta1                      from k8s.io/client-go/informers/node
+        k8s.io/client-go/informers/policy                            from k8s.io/client-go/informers
+        k8s.io/client-go/informers/policy/v1                         from k8s.io/client-go/informers/policy
+        k8s.io/client-go/informers/policy/v1beta1                    from k8s.io/client-go/informers/policy
+        k8s.io/client-go/informers/rbac                              from k8s.io/client-go/informers
+        k8s.io/client-go/informers/rbac/v1                           from k8s.io/client-go/informers/rbac
+        k8s.io/client-go/informers/rbac/v1alpha1                     from k8s.io/client-go/informers/rbac
+        k8s.io/client-go/informers/rbac/v1beta1                      from k8s.io/client-go/informers/rbac
+        k8s.io/client-go/informers/resource                          from k8s.io/client-go/informers
+        k8s.io/client-go/informers/resource/v1alpha3                 from k8s.io/client-go/informers/resource
+        k8s.io/client-go/informers/resource/v1beta1                  from k8s.io/client-go/informers/resource
+        k8s.io/client-go/informers/scheduling                        from k8s.io/client-go/informers
+        k8s.io/client-go/informers/scheduling/v1                     from k8s.io/client-go/informers/scheduling
+        k8s.io/client-go/informers/scheduling/v1alpha1               from k8s.io/client-go/informers/scheduling
+        k8s.io/client-go/informers/scheduling/v1beta1                from k8s.io/client-go/informers/scheduling
+        k8s.io/client-go/informers/storage                           from k8s.io/client-go/informers
+        k8s.io/client-go/informers/storage/v1                        from k8s.io/client-go/informers/storage
+        k8s.io/client-go/informers/storage/v1alpha1                  from k8s.io/client-go/informers/storage
+        k8s.io/client-go/informers/storage/v1beta1                   from k8s.io/client-go/informers/storage
+        k8s.io/client-go/informers/storagemigration                  from k8s.io/client-go/informers
+        k8s.io/client-go/informers/storagemigration/v1alpha1         from k8s.io/client-go/informers/storagemigration
+        k8s.io/client-go/kubernetes                                  from k8s.io/client-go/tools/leaderelection/resourcelock+
         k8s.io/client-go/kubernetes/scheme                           from k8s.io/client-go/discovery+
         k8s.io/client-go/kubernetes/typed/admissionregistration/v1   from k8s.io/client-go/kubernetes
         k8s.io/client-go/kubernetes/typed/admissionregistration/v1alpha1 from k8s.io/client-go/kubernetes
@@ -511,6 +585,7 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
         k8s.io/client-go/kubernetes/typed/certificates/v1alpha1      from k8s.io/client-go/kubernetes
         k8s.io/client-go/kubernetes/typed/certificates/v1beta1       from k8s.io/client-go/kubernetes
         k8s.io/client-go/kubernetes/typed/coordination/v1            from k8s.io/client-go/kubernetes+
+        k8s.io/client-go/kubernetes/typed/coordination/v1alpha2      from k8s.io/client-go/kubernetes+
         k8s.io/client-go/kubernetes/typed/coordination/v1beta1       from k8s.io/client-go/kubernetes
         k8s.io/client-go/kubernetes/typed/core/v1                    from k8s.io/client-go/kubernetes+
         k8s.io/client-go/kubernetes/typed/discovery/v1               from k8s.io/client-go/kubernetes
@@ -533,7 +608,8 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
         k8s.io/client-go/kubernetes/typed/rbac/v1                    from k8s.io/client-go/kubernetes
         k8s.io/client-go/kubernetes/typed/rbac/v1alpha1              from k8s.io/client-go/kubernetes
         k8s.io/client-go/kubernetes/typed/rbac/v1beta1               from k8s.io/client-go/kubernetes
-        k8s.io/client-go/kubernetes/typed/resource/v1alpha2          from k8s.io/client-go/kubernetes
+        k8s.io/client-go/kubernetes/typed/resource/v1alpha3          from k8s.io/client-go/kubernetes
+        k8s.io/client-go/kubernetes/typed/resource/v1beta1           from k8s.io/client-go/kubernetes
         k8s.io/client-go/kubernetes/typed/scheduling/v1              from k8s.io/client-go/kubernetes
         k8s.io/client-go/kubernetes/typed/scheduling/v1alpha1        from k8s.io/client-go/kubernetes
         k8s.io/client-go/kubernetes/typed/scheduling/v1beta1         from k8s.io/client-go/kubernetes
@@ -541,6 +617,56 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
         k8s.io/client-go/kubernetes/typed/storage/v1alpha1           from k8s.io/client-go/kubernetes
         k8s.io/client-go/kubernetes/typed/storage/v1beta1            from k8s.io/client-go/kubernetes
         k8s.io/client-go/kubernetes/typed/storagemigration/v1alpha1  from k8s.io/client-go/kubernetes
+        k8s.io/client-go/listers                                     from k8s.io/client-go/listers/admissionregistration/v1+
+        k8s.io/client-go/listers/admissionregistration/v1            from k8s.io/client-go/informers/admissionregistration/v1
+        k8s.io/client-go/listers/admissionregistration/v1alpha1      from k8s.io/client-go/informers/admissionregistration/v1alpha1
+        k8s.io/client-go/listers/admissionregistration/v1beta1       from k8s.io/client-go/informers/admissionregistration/v1beta1
+        k8s.io/client-go/listers/apiserverinternal/v1alpha1          from k8s.io/client-go/informers/apiserverinternal/v1alpha1
+        k8s.io/client-go/listers/apps/v1                             from k8s.io/client-go/informers/apps/v1
+        k8s.io/client-go/listers/apps/v1beta1                        from k8s.io/client-go/informers/apps/v1beta1
+        k8s.io/client-go/listers/apps/v1beta2                        from k8s.io/client-go/informers/apps/v1beta2
+        k8s.io/client-go/listers/autoscaling/v1                      from k8s.io/client-go/informers/autoscaling/v1
+        k8s.io/client-go/listers/autoscaling/v2                      from k8s.io/client-go/informers/autoscaling/v2
+        k8s.io/client-go/listers/autoscaling/v2beta1                 from k8s.io/client-go/informers/autoscaling/v2beta1
+        k8s.io/client-go/listers/autoscaling/v2beta2                 from k8s.io/client-go/informers/autoscaling/v2beta2
+        k8s.io/client-go/listers/batch/v1                            from k8s.io/client-go/informers/batch/v1
+        k8s.io/client-go/listers/batch/v1beta1                       from k8s.io/client-go/informers/batch/v1beta1
+        k8s.io/client-go/listers/certificates/v1                     from k8s.io/client-go/informers/certificates/v1
+        k8s.io/client-go/listers/certificates/v1alpha1               from k8s.io/client-go/informers/certificates/v1alpha1
+        k8s.io/client-go/listers/certificates/v1beta1                from k8s.io/client-go/informers/certificates/v1beta1
+        k8s.io/client-go/listers/coordination/v1                     from k8s.io/client-go/informers/coordination/v1
+        k8s.io/client-go/listers/coordination/v1alpha2               from k8s.io/client-go/informers/coordination/v1alpha2
+        k8s.io/client-go/listers/coordination/v1beta1                from k8s.io/client-go/informers/coordination/v1beta1
+        k8s.io/client-go/listers/core/v1                             from k8s.io/client-go/informers/core/v1
+        k8s.io/client-go/listers/discovery/v1                        from k8s.io/client-go/informers/discovery/v1
+        k8s.io/client-go/listers/discovery/v1beta1                   from k8s.io/client-go/informers/discovery/v1beta1
+        k8s.io/client-go/listers/events/v1                           from k8s.io/client-go/informers/events/v1
+        k8s.io/client-go/listers/events/v1beta1                      from k8s.io/client-go/informers/events/v1beta1
+        k8s.io/client-go/listers/extensions/v1beta1                  from k8s.io/client-go/informers/extensions/v1beta1
+        k8s.io/client-go/listers/flowcontrol/v1                      from k8s.io/client-go/informers/flowcontrol/v1
+        k8s.io/client-go/listers/flowcontrol/v1beta1                 from k8s.io/client-go/informers/flowcontrol/v1beta1
+        k8s.io/client-go/listers/flowcontrol/v1beta2                 from k8s.io/client-go/informers/flowcontrol/v1beta2
+        k8s.io/client-go/listers/flowcontrol/v1beta3                 from k8s.io/client-go/informers/flowcontrol/v1beta3
+        k8s.io/client-go/listers/networking/v1                       from k8s.io/client-go/informers/networking/v1
+        k8s.io/client-go/listers/networking/v1alpha1                 from k8s.io/client-go/informers/networking/v1alpha1
+        k8s.io/client-go/listers/networking/v1beta1                  from k8s.io/client-go/informers/networking/v1beta1
+        k8s.io/client-go/listers/node/v1                             from k8s.io/client-go/informers/node/v1
+        k8s.io/client-go/listers/node/v1alpha1                       from k8s.io/client-go/informers/node/v1alpha1
+        k8s.io/client-go/listers/node/v1beta1                        from k8s.io/client-go/informers/node/v1beta1
+        k8s.io/client-go/listers/policy/v1                           from k8s.io/client-go/informers/policy/v1
+        k8s.io/client-go/listers/policy/v1beta1                      from k8s.io/client-go/informers/policy/v1beta1
+        k8s.io/client-go/listers/rbac/v1                             from k8s.io/client-go/informers/rbac/v1
+        k8s.io/client-go/listers/rbac/v1alpha1                       from k8s.io/client-go/informers/rbac/v1alpha1
+        k8s.io/client-go/listers/rbac/v1beta1                        from k8s.io/client-go/informers/rbac/v1beta1
+        k8s.io/client-go/listers/resource/v1alpha3                   from k8s.io/client-go/informers/resource/v1alpha3
+        k8s.io/client-go/listers/resource/v1beta1                    from k8s.io/client-go/informers/resource/v1beta1
+        k8s.io/client-go/listers/scheduling/v1                       from k8s.io/client-go/informers/scheduling/v1
+        k8s.io/client-go/listers/scheduling/v1alpha1                 from k8s.io/client-go/informers/scheduling/v1alpha1
+        k8s.io/client-go/listers/scheduling/v1beta1                  from k8s.io/client-go/informers/scheduling/v1beta1
+        k8s.io/client-go/listers/storage/v1                          from k8s.io/client-go/informers/storage/v1
+        k8s.io/client-go/listers/storage/v1alpha1                    from k8s.io/client-go/informers/storage/v1alpha1
+        k8s.io/client-go/listers/storage/v1beta1                     from k8s.io/client-go/informers/storage/v1beta1
+        k8s.io/client-go/listers/storagemigration/v1alpha1           from k8s.io/client-go/informers/storagemigration/v1alpha1
         k8s.io/client-go/metadata                                    from sigs.k8s.io/controller-runtime/pkg/cache/internal+
         k8s.io/client-go/openapi                                     from k8s.io/client-go/discovery
         k8s.io/client-go/pkg/apis/clientauthentication               from k8s.io/client-go/pkg/apis/clientauthentication/install+
@@ -552,6 +678,7 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
         k8s.io/client-go/rest                                        from k8s.io/client-go/discovery+
         k8s.io/client-go/rest/watch                                  from k8s.io/client-go/rest
         k8s.io/client-go/restmapper                                  from sigs.k8s.io/controller-runtime/pkg/client/apiutil
+        k8s.io/client-go/testing                                     from k8s.io/client-go/gentype
         k8s.io/client-go/tools/auth                                  from k8s.io/client-go/tools/clientcmd
         k8s.io/client-go/tools/cache                                 from sigs.k8s.io/controller-runtime/pkg/cache+
         k8s.io/client-go/tools/cache/synctrack                       from k8s.io/client-go/tools/cache
@@ -568,11 +695,14 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
         k8s.io/client-go/tools/record/util                           from k8s.io/client-go/tools/record
         k8s.io/client-go/tools/reference                             from k8s.io/client-go/kubernetes/typed/core/v1+
         k8s.io/client-go/transport                                   from k8s.io/client-go/plugin/pkg/client/auth/exec+
+        k8s.io/client-go/util/apply                                  from k8s.io/client-go/dynamic+
         k8s.io/client-go/util/cert                                   from k8s.io/client-go/rest+
         k8s.io/client-go/util/connrotation                           from k8s.io/client-go/plugin/pkg/client/auth/exec+
+        k8s.io/client-go/util/consistencydetector                    from k8s.io/client-go/dynamic+
         k8s.io/client-go/util/flowcontrol                            from k8s.io/client-go/kubernetes+
         k8s.io/client-go/util/homedir                                from k8s.io/client-go/tools/clientcmd
         k8s.io/client-go/util/keyutil                                from k8s.io/client-go/util/cert
+        k8s.io/client-go/util/watchlist                              from k8s.io/client-go/dynamic+
         k8s.io/client-go/util/workqueue                              from k8s.io/client-go/transport+
         k8s.io/klog/v2                                               from k8s.io/apimachinery/pkg/api/meta+
         k8s.io/klog/v2/internal/buffer                               from k8s.io/klog/v2
@@ -593,11 +723,12 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
         k8s.io/utils/buffer                                          from k8s.io/client-go/tools/cache
         k8s.io/utils/clock                                           from k8s.io/apimachinery/pkg/util/cache+
         k8s.io/utils/clock/testing                                   from k8s.io/client-go/util/flowcontrol
+        k8s.io/utils/internal/third_party/forked/golang/golang-lru   from k8s.io/utils/lru
         k8s.io/utils/internal/third_party/forked/golang/net          from k8s.io/utils/net
+        k8s.io/utils/lru                                             from k8s.io/client-go/tools/record
         k8s.io/utils/net                                             from k8s.io/apimachinery/pkg/util/net+
         k8s.io/utils/pointer                                         from k8s.io/apiextensions-apiserver/pkg/apis/apiextensions/v1+
         k8s.io/utils/ptr                                             from k8s.io/client-go/tools/cache+
-        k8s.io/utils/strings/slices                                  from k8s.io/apimachinery/pkg/labels
         k8s.io/utils/trace                                           from k8s.io/client-go/tools/cache
         sigs.k8s.io/controller-runtime/pkg/builder                   from tailscale.com/cmd/k8s-operator
         sigs.k8s.io/controller-runtime/pkg/cache                     from sigs.k8s.io/controller-runtime/pkg/cluster+
@@ -630,12 +761,12 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
         sigs.k8s.io/controller-runtime/pkg/metrics                   from sigs.k8s.io/controller-runtime/pkg/certwatcher/metrics+
         sigs.k8s.io/controller-runtime/pkg/metrics/server            from sigs.k8s.io/controller-runtime/pkg/manager
         sigs.k8s.io/controller-runtime/pkg/predicate                 from sigs.k8s.io/controller-runtime/pkg/builder+
-        sigs.k8s.io/controller-runtime/pkg/ratelimiter               from sigs.k8s.io/controller-runtime/pkg/controller+
         sigs.k8s.io/controller-runtime/pkg/reconcile                 from sigs.k8s.io/controller-runtime/pkg/builder+
         sigs.k8s.io/controller-runtime/pkg/recorder                  from sigs.k8s.io/controller-runtime/pkg/leaderelection+
         sigs.k8s.io/controller-runtime/pkg/source                    from sigs.k8s.io/controller-runtime/pkg/builder+
         sigs.k8s.io/controller-runtime/pkg/webhook                   from sigs.k8s.io/controller-runtime/pkg/manager
         sigs.k8s.io/controller-runtime/pkg/webhook/admission         from sigs.k8s.io/controller-runtime/pkg/builder+
+        sigs.k8s.io/controller-runtime/pkg/webhook/admission/metrics from sigs.k8s.io/controller-runtime/pkg/webhook/admission
         sigs.k8s.io/controller-runtime/pkg/webhook/conversion        from sigs.k8s.io/controller-runtime/pkg/builder
         sigs.k8s.io/controller-runtime/pkg/webhook/internal/metrics  from sigs.k8s.io/controller-runtime/pkg/webhook+
         sigs.k8s.io/json                                             from k8s.io/apimachinery/pkg/runtime/serializer/json+
@@ -646,10 +777,10 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
         sigs.k8s.io/structured-merge-diff/v4/typed                   from k8s.io/apimachinery/pkg/util/managedfields+
         sigs.k8s.io/structured-merge-diff/v4/value                   from k8s.io/apimachinery/pkg/runtime+
         sigs.k8s.io/yaml                                             from k8s.io/apimachinery/pkg/runtime/serializer/json+
-        sigs.k8s.io/yaml/goyaml.v2                                   from sigs.k8s.io/yaml
+        sigs.k8s.io/yaml/goyaml.v2                                   from sigs.k8s.io/yaml+
         tailscale.com                                                from tailscale.com/version
         tailscale.com/appc                                           from tailscale.com/ipn/ipnlocal
-        tailscale.com/atomicfile                                     from tailscale.com/ipn+
+     💣 tailscale.com/atomicfile                                     from tailscale.com/ipn+
         tailscale.com/client/tailscale                               from tailscale.com/client/web+
         tailscale.com/client/tailscale/apitype                       from tailscale.com/client/tailscale+
         tailscale.com/client/web                                     from tailscale.com/ipn/ipnlocal
@@ -658,6 +789,7 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
         tailscale.com/control/controlbase                            from tailscale.com/control/controlhttp+
         tailscale.com/control/controlclient                          from tailscale.com/ipn/ipnlocal+
         tailscale.com/control/controlhttp                            from tailscale.com/control/controlclient
+        tailscale.com/control/controlhttp/controlhttpcommon          from tailscale.com/control/controlhttp
         tailscale.com/control/controlknobs                           from tailscale.com/control/controlclient+
         tailscale.com/derp                                           from tailscale.com/derp/derphttp+
         tailscale.com/derp/derphttp                                  from tailscale.com/ipn/localapi+
@@ -669,6 +801,10 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
         tailscale.com/drive                                          from tailscale.com/client/tailscale+
         tailscale.com/envknob                                        from tailscale.com/client/tailscale+
         tailscale.com/envknob/featureknob                            from tailscale.com/client/web+
+        tailscale.com/feature                                        from tailscale.com/feature/wakeonlan+
+        tailscale.com/feature/condregister                           from tailscale.com/tsnet
+   L    tailscale.com/feature/tap                                    from tailscale.com/feature/condregister
+        tailscale.com/feature/wakeonlan                              from tailscale.com/feature/condregister
         tailscale.com/health                                         from tailscale.com/control/controlclient+
         tailscale.com/health/healthmsg                               from tailscale.com/ipn/ipnlocal
         tailscale.com/hostinfo                                       from tailscale.com/client/web+
@@ -703,6 +839,7 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
         tailscale.com/logtail/backoff                                from tailscale.com/control/controlclient+
         tailscale.com/logtail/filch                                  from tailscale.com/log/sockstatlog+
         tailscale.com/metrics                                        from tailscale.com/derp+
+        tailscale.com/net/bakedroots                                 from tailscale.com/net/tlsdial+
         tailscale.com/net/captivedetection                           from tailscale.com/ipn/ipnlocal+
         tailscale.com/net/connstats                                  from tailscale.com/net/tstun+
         tailscale.com/net/dns                                        from tailscale.com/ipn/ipnlocal+
@@ -740,7 +877,6 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
         tailscale.com/net/tsdial                                     from tailscale.com/control/controlclient+
      💣 tailscale.com/net/tshttpproxy                                from tailscale.com/clientupdate/distsign+
         tailscale.com/net/tstun                                      from tailscale.com/tsd+
-        tailscale.com/net/wsconn                                     from tailscale.com/control/controlhttp+
         tailscale.com/omit                                           from tailscale.com/ipn/conffile
         tailscale.com/paths                                          from tailscale.com/client/tailscale+
      💣 tailscale.com/portlist                                       from tailscale.com/ipn/ipnlocal
@@ -775,6 +911,7 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
         tailscale.com/types/persist                                  from tailscale.com/control/controlclient+
         tailscale.com/types/preftype                                 from tailscale.com/ipn+
         tailscale.com/types/ptr                                      from tailscale.com/cmd/k8s-operator+
+        tailscale.com/types/result                                   from tailscale.com/util/lineiter
         tailscale.com/types/structs                                  from tailscale.com/control/controlclient+
         tailscale.com/types/tkatype                                  from tailscale.com/client/tailscale+
         tailscale.com/types/views                                    from tailscale.com/appc+
@@ -792,7 +929,7 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
      💣 tailscale.com/util/hashx                                     from tailscale.com/util/deephash
         tailscale.com/util/httphdr                                   from tailscale.com/ipn/ipnlocal+
         tailscale.com/util/httpm                                     from tailscale.com/client/tailscale+
-        tailscale.com/util/lineread                                  from tailscale.com/hostinfo+
+        tailscale.com/util/lineiter                                  from tailscale.com/hostinfo+
    L    tailscale.com/util/linuxfw                                   from tailscale.com/net/netns+
         tailscale.com/util/mak                                       from tailscale.com/appc+
         tailscale.com/util/multierr                                  from tailscale.com/control/controlclient+
@@ -821,7 +958,6 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
         tailscale.com/util/systemd                                   from tailscale.com/control/controlclient+
         tailscale.com/util/testenv                                   from tailscale.com/control/controlclient+
         tailscale.com/util/truncate                                  from tailscale.com/logtail
-        tailscale.com/util/uniq                                      from tailscale.com/ipn/ipnlocal+
         tailscale.com/util/usermetric                                from tailscale.com/health+
         tailscale.com/util/vizerror                                  from tailscale.com/tailcfg+
      💣 tailscale.com/util/winutil                                   from tailscale.com/clientupdate+
@@ -882,7 +1018,7 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
         golang.org/x/oauth2/clientcredentials                        from tailscale.com/cmd/k8s-operator
         golang.org/x/oauth2/internal                                 from golang.org/x/oauth2+
         golang.org/x/sync/errgroup                                   from github.com/mdlayher/socket+
-        golang.org/x/sys/cpu                                         from github.com/josharian/native+
+        golang.org/x/sys/cpu                                         from github.com/tailscale/certstore+
   LD    golang.org/x/sys/unix                                        from github.com/fsnotify/fsnotify+
    W    golang.org/x/sys/windows                                     from github.com/dblohm7/wingoes+
    W    golang.org/x/sys/windows/registry                            from github.com/dblohm7/wingoes+

cmd/k8s-operator/deploy/chart/templates/deployment.yaml

@@ -35,9 +35,13 @@ spec:
         {{- toYaml . | nindent 8 }}
       {{- end }}
       volumes:
-      - name: oauth
-        secret:
-          secretName: operator-oauth
+        - name: oauth
+          {{- with .Values.oauthSecretVolume }}
+          {{- toYaml . | nindent 10 }}
+          {{- else }}
+          secret:
+            secretName: operator-oauth
+          {{- end }}
       containers:
         - name: operator
           {{- with .Values.operatorConfig.securityContext }}
@@ -81,6 +85,14 @@ spec:
             - name: PROXY_DEFAULT_CLASS
               value: {{ .Values.proxyConfig.defaultProxyClass }}
             {{- end }}
+            - name: POD_NAME
+              valueFrom:
+                fieldRef:
+                  fieldPath: metadata.name
+            - name: POD_UID
+              valueFrom:
+                fieldRef:
+                  fieldPath: metadata.uid
             {{- with .Values.operatorConfig.extraEnv }}
             {{- toYaml . | nindent 12 }}
             {{- end }}

cmd/k8s-operator/deploy/chart/templates/ingressclass.yaml

@@ -1,3 +1,4 @@
+{{- if .Values.ingressClass.enabled }}
 apiVersion: networking.k8s.io/v1
 kind: IngressClass
 metadata:
@@ -6,3 +7,4 @@ metadata:
 spec:
   controller: tailscale.com/ts-ingress # controller name currently can not be changed
   # parameters: {} # currently no parameters are supported
+{{- end }}

cmd/k8s-operator/deploy/chart/templates/operator-rbac.yaml

@@ -6,6 +6,10 @@ kind: ServiceAccount
 metadata:
   name: operator
   namespace: {{ .Release.Namespace }}
+  {{- with .Values.operatorConfig.serviceAccountAnnotations }}
+  annotations:
+    {{- toYaml . | nindent 4 }}
+  {{- end }}
 ---
 apiVersion: rbac.authorization.k8s.io/v1
 kind: ClusterRole
@@ -30,6 +34,10 @@ rules:
 - apiGroups: ["tailscale.com"]
   resources: ["recorders", "recorders/status"]
   verbs: ["get", "list", "watch", "update"]
+- apiGroups: ["apiextensions.k8s.io"]
+  resources: ["customresourcedefinitions"]
+  verbs: ["get", "list", "watch"]
+  resourceNames: ["servicemonitors.monitoring.coreos.com"]
 ---
 apiVersion: rbac.authorization.k8s.io/v1
 kind: ClusterRoleBinding
@@ -65,6 +73,9 @@ rules:
 - apiGroups: ["rbac.authorization.k8s.io"]
   resources: ["roles", "rolebindings"]
   verbs: ["get", "create", "patch", "update", "list", "watch"]
+- apiGroups: ["monitoring.coreos.com"]
+  resources: ["servicemonitors"]
+  verbs: ["get", "list", "update", "create", "delete"]
 ---
 apiVersion: rbac.authorization.k8s.io/v1
 kind: RoleBinding

cmd/k8s-operator/deploy/chart/templates/proxy-rbac.yaml

@@ -16,6 +16,9 @@ rules:
 - apiGroups: [""]
   resources: ["secrets"]
   verbs: ["create","delete","deletecollection","get","list","patch","update","watch"]
+- apiGroups: [""]
+  resources: ["events"]
+  verbs: ["create", "patch", "get"]
 ---
 apiVersion: rbac.authorization.k8s.io/v1
 kind: RoleBinding

cmd/k8s-operator/deploy/chart/values.yaml

@@ -3,11 +3,26 @@
 
 # Operator oauth credentials. If set a Kubernetes Secret with the provided
 # values will be created in the operator namespace. If unset a Secret named
-# operator-oauth must be precreated.
+# operator-oauth must be precreated or oauthSecretVolume needs to be adjusted.
+# This block will be overridden by oauthSecretVolume, if set.
 oauth: {}
   # clientId: ""
   # clientSecret: ""
 
+# Secret volume.
+# If set it defines the volume the oauth secrets will be mounted from.
+# The volume needs to contain two files named `client_id` and `client_secret`.
+# If unset the volume will reference the Secret named operator-oauth.
+# This block will override the oauth block.
+oauthSecretVolume: {}
+  # csi:
+  #   driver: secrets-store.csi.k8s.io
+  #   readOnly: true
+  #   volumeAttributes:
+  #     secretProviderClass: tailscale-oauth
+  #
+  ## NAME is pre-defined!
+
 # installCRDs determines whether tailscale.com CRDs should be installed as part
 # of chart installation. We do not use Helm's CRD installation mechanism as that
 # does not allow for upgrading CRDs.
@@ -40,6 +55,9 @@ operatorConfig:
   podAnnotations: {}
   podLabels: {}
 
+  serviceAccountAnnotations: {}
+  # eks.amazonaws.com/role-arn: arn:aws:iam::123456789012:role/tailscale-operator-role
+
   tolerations: []
 
   affinity: {}
@@ -54,6 +72,9 @@ operatorConfig:
   # - name: EXTRA_VAR2
   #   value: "value2"
 
+# In the case that you already have a tailscale ingressclass in your cluster (or vcluster), you can disable the creation here
+ingressClass:
+  enabled: true
 
 # proxyConfig contains configuraton that will be applied to any ingress/egress
 # proxies created by the operator.

cmd/k8s-operator/deploy/crds/tailscale.com_connectors.yaml

@@ -2,7 +2,7 @@ apiVersion: apiextensions.k8s.io/v1
 kind: CustomResourceDefinition
 metadata:
   annotations:
-    controller-gen.kubebuilder.io/version: v0.15.1-0.20240618033008-7824932b0cab
+    controller-gen.kubebuilder.io/version: v0.17.0
   name: connectors.tailscale.com
 spec:
   group: tailscale.com
@@ -24,6 +24,10 @@ spec:
           jsonPath: .status.isExitNode
           name: IsExitNode
           type: string
+        - description: Whether this Connector instance is an app connector.
+          jsonPath: .status.isAppConnector
+          name: IsAppConnector
+          type: string
         - description: Status of the deployed Connector resources.
           jsonPath: .status.conditions[?(@.type == "ConnectorReady")].reason
           name: Status
@@ -66,10 +70,40 @@ spec:
                 https://git.k8s.io/community/contributors/devel/sig-architecture/api-conventions.md#spec-and-status
               type: object
               properties:
+                appConnector:
+                  description: |-
+                    AppConnector defines whether the Connector device should act as a Tailscale app connector. A Connector that is
+                    configured as an app connector cannot be a subnet router or an exit node. If this field is unset, the
+                    Connector does not act as an app connector.
+                    Note that you will need to manually configure the permissions and the domains for the app connector via the
+                    Admin panel.
+                    Note also that the main tested and supported use case of this config option is to deploy an app connector on
+                    Kubernetes to access SaaS applications available on the public internet. Using the app connector to expose
+                    cluster workloads or other internal workloads to tailnet might work, but this is not a use case that we have
+                    tested or optimised for.
+                    If you are using the app connector to access SaaS applications because you need a predictable egress IP that
+                    can be whitelisted, it is also your responsibility to ensure that cluster traffic from the connector flows
+                    via that predictable IP, for example by enforcing that cluster egress traffic is routed via an egress NAT
+                    device with a static IP address.
+                    https://tailscale.com/kb/1281/app-connectors
+                  type: object
+                  properties:
+                    routes:
+                      description: |-
+                        Routes are optional preconfigured routes for the domains routed via the app connector.
+                        If not set, routes for the domains will be discovered dynamically.
+                        If set, the app connector will immediately be able to route traffic using the preconfigured routes, but may
+                        also dynamically discover other routes.
+                        https://tailscale.com/kb/1332/apps-best-practices#preconfiguration
+                      type: array
+                      minItems: 1
+                      items:
+                        type: string
+                        format: cidr
                 exitNode:
                   description: |-
-                    ExitNode defines whether the Connector node should act as a
-                    Tailscale exit node. Defaults to false.
+                    ExitNode defines whether the Connector device should act as a Tailscale exit node. Defaults to false.
+                    This field is mutually exclusive with the appConnector field.
                     https://tailscale.com/kb/1103/exit-nodes
                   type: boolean
                 hostname:
@@ -90,9 +124,11 @@ spec:
                   type: string
                 subnetRouter:
                   description: |-
-                    SubnetRouter defines subnet routes that the Connector node should
-                    expose to tailnet. If unset, none are exposed.
+                    SubnetRouter defines subnet routes that the Connector device should
+                    expose to tailnet as a Tailscale subnet router.
                     https://tailscale.com/kb/1019/subnets/
+                    If this field is unset, the device does not get configured as a Tailscale subnet router.
+                    This field is mutually exclusive with the appConnector field.
                   type: object
                   required:
                     - advertiseRoutes
@@ -125,8 +161,10 @@ spec:
                     type: string
                     pattern: ^tag:[a-zA-Z][a-zA-Z0-9-]*$
               x-kubernetes-validations:
-                - rule: has(self.subnetRouter) || self.exitNode == true
-                  message: A Connector needs to be either an exit node or a subnet router, or both.
+                - rule: has(self.subnetRouter) || (has(self.exitNode) && self.exitNode == true) || has(self.appConnector)
+                  message: A Connector needs to have at least one of exit node, subnet router or app connector configured.
+                - rule: '!((has(self.subnetRouter) || (has(self.exitNode)  && self.exitNode == true)) && has(self.appConnector))'
+                  message: The appConnector field is mutually exclusive with exitNode and subnetRouter fields.
             status:
               description: |-
                 ConnectorStatus describes the status of the Connector. This is set
@@ -200,6 +238,9 @@ spec:
                     If MagicDNS is enabled in your tailnet, it is the MagicDNS name of the
                     node.
                   type: string
+                isAppConnector:
+                  description: IsAppConnector is set to true if the Connector acts as an app connector.
+                  type: boolean
                 isExitNode:
                   description: IsExitNode is set to true if the Connector acts as an exit node.
                   type: boolean

cmd/k8s-operator/deploy/crds/tailscale.com_dnsconfigs.yaml

@@ -2,7 +2,7 @@ apiVersion: apiextensions.k8s.io/v1
 kind: CustomResourceDefinition
 metadata:
   annotations:
-    controller-gen.kubebuilder.io/version: v0.15.1-0.20240618033008-7824932b0cab
+    controller-gen.kubebuilder.io/version: v0.17.0
   name: dnsconfigs.tailscale.com
 spec:
   group: tailscale.com

cmd/k8s-operator/deploy/crds/tailscale.com_proxyclasses.yaml

@@ -2,7 +2,7 @@ apiVersion: apiextensions.k8s.io/v1
 kind: CustomResourceDefinition
 metadata:
   annotations:
-    controller-gen.kubebuilder.io/version: v0.15.1-0.20240618033008-7824932b0cab
+    controller-gen.kubebuilder.io/version: v0.17.0
   name: proxyclasses.tailscale.com
 spec:
   group: tailscale.com
@@ -73,9 +73,45 @@ spec:
                     enable:
                       description: |-
                         Setting enable to true will make the proxy serve Tailscale metrics
-                        at <pod-ip>:9001/debug/metrics.
+                        at <pod-ip>:9002/metrics.
+                        A metrics Service named <proxy-statefulset>-metrics will also be created in the operator's namespace and will
+                        serve the metrics at <service-ip>:9002/metrics.
+
+                        In 1.78.x and 1.80.x, this field also serves as the default value for
+                        .spec.statefulSet.pod.tailscaleContainer.debug.enable. From 1.82.0, both
+                        fields will independently default to false.
+
                         Defaults to false.
                       type: boolean
+                    serviceMonitor:
+                      description: |-
+                        Enable to create a Prometheus ServiceMonitor for scraping the proxy's Tailscale metrics.
+                        The ServiceMonitor will select the metrics Service that gets created when metrics are enabled.
+                        The ingested metrics for each Service monitor will have labels to identify the proxy:
+                        ts_proxy_type: ingress_service|ingress_resource|connector|proxygroup
+                        ts_proxy_parent_name: name of the parent resource (i.e name of the Connector, Tailscale Ingress, Tailscale Service or ProxyGroup)
+                        ts_proxy_parent_namespace: namespace of the parent resource (if the parent resource is not cluster scoped)
+                        job: ts_<proxy type>_[<parent namespace>]_<parent_name>
+                      type: object
+                      required:
+                        - enable
+                      properties:
+                        enable:
+                          description: If Enable is set to true, a Prometheus ServiceMonitor will be created. Enable can only be set to true if metrics are enabled.
+                          type: boolean
+                        labels:
+                          description: |-
+                            Labels to add to the ServiceMonitor.
+                            Labels must be valid Kubernetes labels.
+                            https://kubernetes.io/docs/concepts/overview/working-with-objects/labels/#syntax-and-character-set
+                          type: object
+                          additionalProperties:
+                            type: string
+                            maxLength: 63
+                            pattern: ^(([a-zA-Z0-9][-._a-zA-Z0-9]*)?[a-zA-Z0-9])?$
+                  x-kubernetes-validations:
+                    - rule: '!(has(self.serviceMonitor) && self.serviceMonitor.enable  && !self.enable)'
+                      message: ServiceMonitor can only be enabled if metrics are enabled
                 statefulSet:
                   description: |-
                     Configuration parameters for the proxy's StatefulSet. Tailscale
@@ -107,6 +143,8 @@ spec:
                       type: object
                       additionalProperties:
                         type: string
+                        maxLength: 63
+                        pattern: ^(([a-zA-Z0-9][-._a-zA-Z0-9]*)?[a-zA-Z0-9])?$
                     pod:
                       description: Configuration for the proxy Pod.
                       type: object
@@ -390,7 +428,7 @@ spec:
                                               pod labels will be ignored. The default value is empty.
                                               The same key is forbidden to exist in both matchLabelKeys and labelSelector.
                                               Also, matchLabelKeys cannot be set when labelSelector isn't set.
-                                              This is an alpha field and requires enabling MatchLabelKeysInPodAffinity feature gate.
+                                              This is a beta field and requires enabling MatchLabelKeysInPodAffinity feature gate (enabled by default).
                                             type: array
                                             items:
                                               type: string
@@ -405,7 +443,7 @@ spec:
                                               pod labels will be ignored. The default value is empty.
                                               The same key is forbidden to exist in both mismatchLabelKeys and labelSelector.
                                               Also, mismatchLabelKeys cannot be set when labelSelector isn't set.
-                                              This is an alpha field and requires enabling MatchLabelKeysInPodAffinity feature gate.
+                                              This is a beta field and requires enabling MatchLabelKeysInPodAffinity feature gate (enabled by default).
                                             type: array
                                             items:
                                               type: string
@@ -562,7 +600,7 @@ spec:
                                           pod labels will be ignored. The default value is empty.
                                           The same key is forbidden to exist in both matchLabelKeys and labelSelector.
                                           Also, matchLabelKeys cannot be set when labelSelector isn't set.
-                                          This is an alpha field and requires enabling MatchLabelKeysInPodAffinity feature gate.
+                                          This is a beta field and requires enabling MatchLabelKeysInPodAffinity feature gate (enabled by default).
                                         type: array
                                         items:
                                           type: string
@@ -577,7 +615,7 @@ spec:
                                           pod labels will be ignored. The default value is empty.
                                           The same key is forbidden to exist in both mismatchLabelKeys and labelSelector.
                                           Also, mismatchLabelKeys cannot be set when labelSelector isn't set.
-                                          This is an alpha field and requires enabling MatchLabelKeysInPodAffinity feature gate.
+                                          This is a beta field and requires enabling MatchLabelKeysInPodAffinity feature gate (enabled by default).
                                         type: array
                                         items:
                                           type: string
@@ -735,7 +773,7 @@ spec:
                                               pod labels will be ignored. The default value is empty.
                                               The same key is forbidden to exist in both matchLabelKeys and labelSelector.
                                               Also, matchLabelKeys cannot be set when labelSelector isn't set.
-                                              This is an alpha field and requires enabling MatchLabelKeysInPodAffinity feature gate.
+                                              This is a beta field and requires enabling MatchLabelKeysInPodAffinity feature gate (enabled by default).
                                             type: array
                                             items:
                                               type: string
@@ -750,7 +788,7 @@ spec:
                                               pod labels will be ignored. The default value is empty.
                                               The same key is forbidden to exist in both mismatchLabelKeys and labelSelector.
                                               Also, mismatchLabelKeys cannot be set when labelSelector isn't set.
-                                              This is an alpha field and requires enabling MatchLabelKeysInPodAffinity feature gate.
+                                              This is a beta field and requires enabling MatchLabelKeysInPodAffinity feature gate (enabled by default).
                                             type: array
                                             items:
                                               type: string
@@ -907,7 +945,7 @@ spec:
                                           pod labels will be ignored. The default value is empty.
                                           The same key is forbidden to exist in both matchLabelKeys and labelSelector.
                                           Also, matchLabelKeys cannot be set when labelSelector isn't set.
-                                          This is an alpha field and requires enabling MatchLabelKeysInPodAffinity feature gate.
+                                          This is a beta field and requires enabling MatchLabelKeysInPodAffinity feature gate (enabled by default).
                                         type: array
                                         items:
                                           type: string
@@ -922,7 +960,7 @@ spec:
                                           pod labels will be ignored. The default value is empty.
                                           The same key is forbidden to exist in both mismatchLabelKeys and labelSelector.
                                           Also, mismatchLabelKeys cannot be set when labelSelector isn't set.
-                                          This is an alpha field and requires enabling MatchLabelKeysInPodAffinity feature gate.
+                                          This is a beta field and requires enabling MatchLabelKeysInPodAffinity feature gate (enabled by default).
                                         type: array
                                         items:
                                           type: string
@@ -1036,6 +1074,8 @@ spec:
                           type: object
                           additionalProperties:
                             type: string
+                            maxLength: 63
+                            pattern: ^(([a-zA-Z0-9][-._a-zA-Z0-9]*)?[a-zA-Z0-9])?$
                         nodeName:
                           description: |-
                             Proxy Pod's node name.
@@ -1134,6 +1174,32 @@ spec:
                                 Note that this field cannot be set when spec.os.name is windows.
                               type: integer
                               format: int64
+                            seLinuxChangePolicy:
+                              description: |-
+                                seLinuxChangePolicy defines how the container's SELinux label is applied to all volumes used by the Pod.
+                                It has no effect on nodes that do not support SELinux or to volumes does not support SELinux.
+                                Valid values are "MountOption" and "Recursive".
+
+                                "Recursive" means relabeling of all files on all Pod volumes by the container runtime.
+                                This may be slow for large volumes, but allows mixing privileged and unprivileged Pods sharing the same volume on the same node.
+
+                                "MountOption" mounts all eligible Pod volumes with `-o context` mount option.
+                                This requires all Pods that share the same volume to use the same SELinux label.
+                                It is not possible to share the same volume among privileged and unprivileged Pods.
+                                Eligible volumes are in-tree FibreChannel and iSCSI volumes, and all CSI volumes
+                                whose CSI driver announces SELinux support by setting spec.seLinuxMount: true in their
+                                CSIDriver instance. Other volumes are always re-labelled recursively.
+                                "MountOption" value is allowed only when SELinuxMount feature gate is enabled.
+
+                                If not specified and SELinuxMount feature gate is enabled, "MountOption" is used.
+                                If not specified and SELinuxMount feature gate is disabled, "MountOption" is used for ReadWriteOncePod volumes
+                                and "Recursive" for all other volumes.
+
+                                This field affects only Pods that have SELinux label set, either in PodSecurityContext or in SecurityContext of all containers.
+
+                                All Pods that use the same volume should use the same seLinuxChangePolicy, otherwise some pods can get stuck in ContainerCreating state.
+                                Note that this field cannot be set when spec.os.name is windows.
+                              type: string
                             seLinuxOptions:
                               description: |-
                                 The SELinux context to be applied to all containers.
@@ -1182,18 +1248,28 @@ spec:
                                   type: string
                             supplementalGroups:
                               description: |-
-                                A list of groups applied to the first process run in each container, in addition
-                                to the container's primary GID, the fsGroup (if specified), and group memberships
-                                defined in the container image for the uid of the container process. If unspecified,
-                                no additional groups are added to any container. Note that group memberships
-                                defined in the container image for the uid of the container process are still effective,
-                                even if they are not included in this list.
+                                A list of groups applied to the first process run in each container, in
+                                addition to the container's primary GID and fsGroup (if specified).  If
+                                the SupplementalGroupsPolicy feature is enabled, the
+                                supplementalGroupsPolicy field determines whether these are in addition
+                                to or instead of any group memberships defined in the container image.
+                                If unspecified, no additional groups are added, though group memberships
+                                defined in the container image may still be used, depending on the
+                                supplementalGroupsPolicy field.
                                 Note that this field cannot be set when spec.os.name is windows.
                               type: array
                               items:
                                 type: integer
                                 format: int64
                               x-kubernetes-list-type: atomic
+                            supplementalGroupsPolicy:
+                              description: |-
+                                Defines how supplemental groups of the first container processes are calculated.
+                                Valid values are "Merge" and "Strict". If not specified, "Merge" is used.
+                                (Alpha) Using the field requires the SupplementalGroupsPolicy feature gate to be enabled
+                                and the container runtime must implement support for this feature.
+                                Note that this field cannot be set when spec.os.name is windows.
+                              type: string
                             sysctls:
                               description: |-
                                 Sysctls hold a list of namespaced sysctls used for the pod. Pods with unsupported
@@ -1249,6 +1325,25 @@ spec:
                           description: Configuration for the proxy container running tailscale.
                           type: object
                           properties:
+                            debug:
+                              description: |-
+                                Configuration for enabling extra debug information in the container.
+                                Not recommended for production use.
+                              type: object
+                              properties:
+                                enable:
+                                  description: |-
+                                    Enable tailscaled's HTTP pprof endpoints at <pod-ip>:9001/debug/pprof/
+                                    and internal debug metrics endpoint at <pod-ip>:9001/debug/metrics, where
+                                    9001 is a container port named "debug". The endpoints and their responses
+                                    may change in backwards incompatible ways in the future, and should not
+                                    be considered stable.
+
+                                    In 1.78.x and 1.80.x, this setting will default to the value of
+                                    .spec.metrics.enable, and requests to the "metrics" port matching the
+                                    mux pattern /debug/ will be forwarded to the "debug" port. In 1.82.x,
+                                    this setting will default to false, and no requests will be proxied.
+                                  type: boolean
                             env:
                               description: |-
                                 List of environment variables to set in the container.
@@ -1330,6 +1425,12 @@ spec:
                                           the Pod where this field is used. It makes that resource available
                                           inside a container.
                                         type: string
+                                      request:
+                                        description: |-
+                                          Request is the name chosen for a request in the referenced claim.
+                                          If empty, everything from the claim is made available, otherwise
+                                          only the result of this request.
+                                        type: string
                                   x-kubernetes-list-map-keys:
                                     - name
                                   x-kubernetes-list-type: map
@@ -1360,11 +1461,12 @@ spec:
                             securityContext:
                               description: |-
                                 Container security context.
-                                Security context specified here will override the security context by the operator.
-                                By default the operator:
-                                - sets 'privileged: true' for the init container
-                                - set NET_ADMIN capability for tailscale container for proxies that
-                                are created for Services or Connector.
+                                Security context specified here will override the security context set by the operator.
+                                By default the operator sets the Tailscale container and the Tailscale init container to privileged
+                                for proxies created for Tailscale ingress and egress Service, Connector and ProxyGroup.
+                                You can reduce the permissions of the Tailscale container to cap NET_ADMIN by
+                                installing device plugin in your cluster and configuring the proxies tun device to be created
+                                by the device plugin, see  https://github.com/tailscale/tailscale/issues/10814#issuecomment-2479977752
                                 https://kubernetes.io/docs/reference/kubernetes-api/workload-resources/pod-v1/#security-context
                               type: object
                               properties:
@@ -1433,7 +1535,7 @@ spec:
                                 procMount:
                                   description: |-
                                     procMount denotes the type of proc mount to use for the containers.
-                                    The default is DefaultProcMount which uses the container runtime defaults for
+                                    The default value is Default which uses the container runtime defaults for
                                     readonly paths and masked paths.
                                     This requires the ProcMountType feature flag to be enabled.
                                     Note that this field cannot be set when spec.os.name is windows.
@@ -1553,6 +1655,25 @@ spec:
                           description: Configuration for the proxy init container that enables forwarding.
                           type: object
                           properties:
+                            debug:
+                              description: |-
+                                Configuration for enabling extra debug information in the container.
+                                Not recommended for production use.
+                              type: object
+                              properties:
+                                enable:
+                                  description: |-
+                                    Enable tailscaled's HTTP pprof endpoints at <pod-ip>:9001/debug/pprof/
+                                    and internal debug metrics endpoint at <pod-ip>:9001/debug/metrics, where
+                                    9001 is a container port named "debug". The endpoints and their responses
+                                    may change in backwards incompatible ways in the future, and should not
+                                    be considered stable.
+
+                                    In 1.78.x and 1.80.x, this setting will default to the value of
+                                    .spec.metrics.enable, and requests to the "metrics" port matching the
+                                    mux pattern /debug/ will be forwarded to the "debug" port. In 1.82.x,
+                                    this setting will default to false, and no requests will be proxied.
+                                  type: boolean
                             env:
                               description: |-
                                 List of environment variables to set in the container.
@@ -1634,6 +1755,12 @@ spec:
                                           the Pod where this field is used. It makes that resource available
                                           inside a container.
                                         type: string
+                                      request:
+                                        description: |-
+                                          Request is the name chosen for a request in the referenced claim.
+                                          If empty, everything from the claim is made available, otherwise
+                                          only the result of this request.
+                                        type: string
                                   x-kubernetes-list-map-keys:
                                     - name
                                   x-kubernetes-list-type: map
@@ -1664,11 +1791,12 @@ spec:
                             securityContext:
                               description: |-
                                 Container security context.
-                                Security context specified here will override the security context by the operator.
-                                By default the operator:
-                                - sets 'privileged: true' for the init container
-                                - set NET_ADMIN capability for tailscale container for proxies that
-                                are created for Services or Connector.
+                                Security context specified here will override the security context set by the operator.
+                                By default the operator sets the Tailscale container and the Tailscale init container to privileged
+                                for proxies created for Tailscale ingress and egress Service, Connector and ProxyGroup.
+                                You can reduce the permissions of the Tailscale container to cap NET_ADMIN by
+                                installing device plugin in your cluster and configuring the proxies tun device to be created
+                                by the device plugin, see  https://github.com/tailscale/tailscale/issues/10814#issuecomment-2479977752
                                 https://kubernetes.io/docs/reference/kubernetes-api/workload-resources/pod-v1/#security-context
                               type: object
                               properties:
@@ -1737,7 +1865,7 @@ spec:
                                 procMount:
                                   description: |-
                                     procMount denotes the type of proc mount to use for the containers.
-                                    The default is DefaultProcMount which uses the container runtime defaults for
+                                    The default value is Default which uses the container runtime defaults for
                                     readonly paths and masked paths.
                                     This requires the ProcMountType feature flag to be enabled.
                                     Note that this field cannot be set when spec.os.name is windows.

cmd/k8s-operator/deploy/crds/tailscale.com_proxygroups.yaml

@@ -2,7 +2,7 @@ apiVersion: apiextensions.k8s.io/v1
 kind: CustomResourceDefinition
 metadata:
   annotations:
-    controller-gen.kubebuilder.io/version: v0.15.1-0.20240618033008-7824932b0cab
+    controller-gen.kubebuilder.io/version: v0.17.0
   name: proxygroups.tailscale.com
 spec:
   group: tailscale.com
@@ -20,9 +20,24 @@ spec:
           jsonPath: .status.conditions[?(@.type == "ProxyGroupReady")].reason
           name: Status
           type: string
+        - description: ProxyGroup type.
+          jsonPath: .spec.type
+          name: Type
+          type: string
       name: v1alpha1
       schema:
         openAPIV3Schema:
+          description: |-
+            ProxyGroup defines a set of Tailscale devices that will act as proxies.
+            Currently only egress ProxyGroups are supported.
+
+            Use the tailscale.com/proxy-group annotation on a Service to specify that
+            the egress proxy should be implemented by a ProxyGroup instead of a single
+            dedicated proxy. In addition to running a highly available set of proxies,
+            ProxyGroup also allows for serving many annotated Services from a single
+            set of proxies to minimise resource consumption.
+
+            More info: https://tailscale.com/kb/1438/kubernetes-operator-cluster-egress
           type: object
           required:
             - spec
@@ -73,6 +88,7 @@ spec:
                     Defaults to 2.
                   type: integer
                   format: int32
+                  minimum: 0
                 tags:
                   description: |-
                     Tags that the Tailscale devices will be tagged with. Defaults to [tag:k8s].
@@ -86,10 +102,16 @@ spec:
                     type: string
                     pattern: ^tag:[a-zA-Z][a-zA-Z0-9-]*$
                 type:
-                  description: Type of the ProxyGroup proxies. Currently the only supported type is egress.
+                  description: |-
+                    Type of the ProxyGroup proxies. Supported types are egress and ingress.
+                    Type is immutable once a ProxyGroup is created.
                   type: string
                   enum:
                     - egress
+                    - ingress
+                  x-kubernetes-validations:
+                    - rule: self == oldSelf
+                      message: ProxyGroup type is immutable
             status:
               description: |-
                 ProxyGroupStatus describes the status of the ProxyGroup resources. This is

cmd/k8s-operator/deploy/crds/tailscale.com_recorders.yaml

@@ -2,7 +2,7 @@ apiVersion: apiextensions.k8s.io/v1
 kind: CustomResourceDefinition
 metadata:
   annotations:
-    controller-gen.kubebuilder.io/version: v0.15.1-0.20240618033008-7824932b0cab
+    controller-gen.kubebuilder.io/version: v0.17.0
   name: recorders.tailscale.com
 spec:
   group: tailscale.com
@@ -27,6 +27,12 @@ spec:
       name: v1alpha1
       schema:
         openAPIV3Schema:
+          description: |-
+            Recorder defines a tsrecorder device for recording SSH sessions. By default,
+            it will store recordings in a local ephemeral volume. If you want to persist
+            recordings, you can configure an S3-compatible API for storage.
+
+            More info: https://tailscale.com/kb/1484/kubernetes-operator-deploying-tsrecorder
           type: object
           required:
             - spec
@@ -366,7 +372,7 @@ spec:
                                               pod labels will be ignored. The default value is empty.
                                               The same key is forbidden to exist in both matchLabelKeys and labelSelector.
                                               Also, matchLabelKeys cannot be set when labelSelector isn't set.
-                                              This is an alpha field and requires enabling MatchLabelKeysInPodAffinity feature gate.
+                                              This is a beta field and requires enabling MatchLabelKeysInPodAffinity feature gate (enabled by default).
                                             type: array
                                             items:
                                               type: string
@@ -381,7 +387,7 @@ spec:
                                               pod labels will be ignored. The default value is empty.
                                               The same key is forbidden to exist in both mismatchLabelKeys and labelSelector.
                                               Also, mismatchLabelKeys cannot be set when labelSelector isn't set.
-                                              This is an alpha field and requires enabling MatchLabelKeysInPodAffinity feature gate.
+                                              This is a beta field and requires enabling MatchLabelKeysInPodAffinity feature gate (enabled by default).
                                             type: array
                                             items:
                                               type: string
@@ -538,7 +544,7 @@ spec:
                                           pod labels will be ignored. The default value is empty.
                                           The same key is forbidden to exist in both matchLabelKeys and labelSelector.
                                           Also, matchLabelKeys cannot be set when labelSelector isn't set.
-                                          This is an alpha field and requires enabling MatchLabelKeysInPodAffinity feature gate.
+                                          This is a beta field and requires enabling MatchLabelKeysInPodAffinity feature gate (enabled by default).
                                         type: array
                                         items:
                                           type: string
@@ -553,7 +559,7 @@ spec:
                                           pod labels will be ignored. The default value is empty.
                                           The same key is forbidden to exist in both mismatchLabelKeys and labelSelector.
                                           Also, mismatchLabelKeys cannot be set when labelSelector isn't set.
-                                          This is an alpha field and requires enabling MatchLabelKeysInPodAffinity feature gate.
+                                          This is a beta field and requires enabling MatchLabelKeysInPodAffinity feature gate (enabled by default).
                                         type: array
                                         items:
                                           type: string
@@ -711,7 +717,7 @@ spec:
                                               pod labels will be ignored. The default value is empty.
                                               The same key is forbidden to exist in both matchLabelKeys and labelSelector.
                                               Also, matchLabelKeys cannot be set when labelSelector isn't set.
-                                              This is an alpha field and requires enabling MatchLabelKeysInPodAffinity feature gate.
+                                              This is a beta field and requires enabling MatchLabelKeysInPodAffinity feature gate (enabled by default).
                                             type: array
                                             items:
                                               type: string
@@ -726,7 +732,7 @@ spec:
                                               pod labels will be ignored. The default value is empty.
                                               The same key is forbidden to exist in both mismatchLabelKeys and labelSelector.
                                               Also, mismatchLabelKeys cannot be set when labelSelector isn't set.
-                                              This is an alpha field and requires enabling MatchLabelKeysInPodAffinity feature gate.
+                                              This is a beta field and requires enabling MatchLabelKeysInPodAffinity feature gate (enabled by default).
                                             type: array
                                             items:
                                               type: string
@@ -883,7 +889,7 @@ spec:
                                           pod labels will be ignored. The default value is empty.
                                           The same key is forbidden to exist in both matchLabelKeys and labelSelector.
                                           Also, matchLabelKeys cannot be set when labelSelector isn't set.
-                                          This is an alpha field and requires enabling MatchLabelKeysInPodAffinity feature gate.
+                                          This is a beta field and requires enabling MatchLabelKeysInPodAffinity feature gate (enabled by default).
                                         type: array
                                         items:
                                           type: string
@@ -898,7 +904,7 @@ spec:
                                           pod labels will be ignored. The default value is empty.
                                           The same key is forbidden to exist in both mismatchLabelKeys and labelSelector.
                                           Also, mismatchLabelKeys cannot be set when labelSelector isn't set.
-                                          This is an alpha field and requires enabling MatchLabelKeysInPodAffinity feature gate.
+                                          This is a beta field and requires enabling MatchLabelKeysInPodAffinity feature gate (enabled by default).
                                         type: array
                                         items:
                                           type: string
@@ -1060,6 +1066,12 @@ spec:
                                           the Pod where this field is used. It makes that resource available
                                           inside a container.
                                         type: string
+                                      request:
+                                        description: |-
+                                          Request is the name chosen for a request in the referenced claim.
+                                          If empty, everything from the claim is made available, otherwise
+                                          only the result of this request.
+                                        type: string
                                   x-kubernetes-list-map-keys:
                                     - name
                                   x-kubernetes-list-type: map
@@ -1159,7 +1171,7 @@ spec:
                                 procMount:
                                   description: |-
                                     procMount denotes the type of proc mount to use for the containers.
-                                    The default is DefaultProcMount which uses the container runtime defaults for
+                                    The default value is Default which uses the container runtime defaults for
                                     readonly paths and masked paths.
                                     This requires the ProcMountType feature flag to be enabled.
                                     Note that this field cannot be set when spec.os.name is windows.
@@ -1395,6 +1407,32 @@ spec:
                                 Note that this field cannot be set when spec.os.name is windows.
                               type: integer
                               format: int64
+                            seLinuxChangePolicy:
+                              description: |-
+                                seLinuxChangePolicy defines how the container's SELinux label is applied to all volumes used by the Pod.
+                                It has no effect on nodes that do not support SELinux or to volumes does not support SELinux.
+                                Valid values are "MountOption" and "Recursive".
+
+                                "Recursive" means relabeling of all files on all Pod volumes by the container runtime.
+                                This may be slow for large volumes, but allows mixing privileged and unprivileged Pods sharing the same volume on the same node.
+
+                                "MountOption" mounts all eligible Pod volumes with `-o context` mount option.
+                                This requires all Pods that share the same volume to use the same SELinux label.
+                                It is not possible to share the same volume among privileged and unprivileged Pods.
+                                Eligible volumes are in-tree FibreChannel and iSCSI volumes, and all CSI volumes
+                                whose CSI driver announces SELinux support by setting spec.seLinuxMount: true in their
+                                CSIDriver instance. Other volumes are always re-labelled recursively.
+                                "MountOption" value is allowed only when SELinuxMount feature gate is enabled.
+
+                                If not specified and SELinuxMount feature gate is enabled, "MountOption" is used.
+                                If not specified and SELinuxMount feature gate is disabled, "MountOption" is used for ReadWriteOncePod volumes
+                                and "Recursive" for all other volumes.
+
+                                This field affects only Pods that have SELinux label set, either in PodSecurityContext or in SecurityContext of all containers.
+
+                                All Pods that use the same volume should use the same seLinuxChangePolicy, otherwise some pods can get stuck in ContainerCreating state.
+                                Note that this field cannot be set when spec.os.name is windows.
+                              type: string
                             seLinuxOptions:
                               description: |-
                                 The SELinux context to be applied to all containers.
@@ -1443,18 +1481,28 @@ spec:
                                   type: string
                             supplementalGroups:
                               description: |-
-                                A list of groups applied to the first process run in each container, in addition
-                                to the container's primary GID, the fsGroup (if specified), and group memberships
-                                defined in the container image for the uid of the container process. If unspecified,
-                                no additional groups are added to any container. Note that group memberships
-                                defined in the container image for the uid of the container process are still effective,
-                                even if they are not included in this list.
+                                A list of groups applied to the first process run in each container, in
+                                addition to the container's primary GID and fsGroup (if specified).  If
+                                the SupplementalGroupsPolicy feature is enabled, the
+                                supplementalGroupsPolicy field determines whether these are in addition
+                                to or instead of any group memberships defined in the container image.
+                                If unspecified, no additional groups are added, though group memberships
+                                defined in the container image may still be used, depending on the
+                                supplementalGroupsPolicy field.
                                 Note that this field cannot be set when spec.os.name is windows.
                               type: array
                               items:
                                 type: integer
                                 format: int64
                               x-kubernetes-list-type: atomic
+                            supplementalGroupsPolicy:
+                              description: |-
+                                Defines how supplemental groups of the first container processes are calculated.
+                                Valid values are "Merge" and "Strict". If not specified, "Merge" is used.
+                                (Alpha) Using the field requires the SupplementalGroupsPolicy feature gate to be enabled
+                                and the container runtime must implement support for this feature.
+                                Note that this field cannot be set when spec.os.name is windows.
+                              type: string
                             sysctls:
                               description: |-
                                 Sysctls hold a list of namespaced sysctls used for the pod. Pods with unsupported

cmd/k8s-operator/deploy/manifests/operator.yaml

@@ -31,7 +31,7 @@ apiVersion: apiextensions.k8s.io/v1
 kind: CustomResourceDefinition
 metadata:
     annotations:
-        controller-gen.kubebuilder.io/version: v0.15.1-0.20240618033008-7824932b0cab
+        controller-gen.kubebuilder.io/version: v0.17.0
     name: connectors.tailscale.com
 spec:
     group: tailscale.com
@@ -53,6 +53,10 @@ spec:
               jsonPath: .status.isExitNode
               name: IsExitNode
               type: string
+            - description: Whether this Connector instance is an app connector.
+              jsonPath: .status.isAppConnector
+              name: IsAppConnector
+              type: string
             - description: Status of the deployed Connector resources.
               jsonPath: .status.conditions[?(@.type == "ConnectorReady")].reason
               name: Status
@@ -91,10 +95,40 @@ spec:
                             More info:
                             https://git.k8s.io/community/contributors/devel/sig-architecture/api-conventions.md#spec-and-status
                         properties:
+                            appConnector:
+                                description: |-
+                                    AppConnector defines whether the Connector device should act as a Tailscale app connector. A Connector that is
+                                    configured as an app connector cannot be a subnet router or an exit node. If this field is unset, the
+                                    Connector does not act as an app connector.
+                                    Note that you will need to manually configure the permissions and the domains for the app connector via the
+                                    Admin panel.
+                                    Note also that the main tested and supported use case of this config option is to deploy an app connector on
+                                    Kubernetes to access SaaS applications available on the public internet. Using the app connector to expose
+                                    cluster workloads or other internal workloads to tailnet might work, but this is not a use case that we have
+                                    tested or optimised for.
+                                    If you are using the app connector to access SaaS applications because you need a predictable egress IP that
+                                    can be whitelisted, it is also your responsibility to ensure that cluster traffic from the connector flows
+                                    via that predictable IP, for example by enforcing that cluster egress traffic is routed via an egress NAT
+                                    device with a static IP address.
+                                    https://tailscale.com/kb/1281/app-connectors
+                                properties:
+                                    routes:
+                                        description: |-
+                                            Routes are optional preconfigured routes for the domains routed via the app connector.
+                                            If not set, routes for the domains will be discovered dynamically.
+                                            If set, the app connector will immediately be able to route traffic using the preconfigured routes, but may
+                                            also dynamically discover other routes.
+                                            https://tailscale.com/kb/1332/apps-best-practices#preconfiguration
+                                        items:
+                                            format: cidr
+                                            type: string
+                                        minItems: 1
+                                        type: array
+                                type: object
                             exitNode:
                                 description: |-
-                                    ExitNode defines whether the Connector node should act as a
-                                    Tailscale exit node. Defaults to false.
+                                    ExitNode defines whether the Connector device should act as a Tailscale exit node. Defaults to false.
+                                    This field is mutually exclusive with the appConnector field.
                                     https://tailscale.com/kb/1103/exit-nodes
                                 type: boolean
                             hostname:
@@ -115,9 +149,11 @@ spec:
                                 type: string
                             subnetRouter:
                                 description: |-
-                                    SubnetRouter defines subnet routes that the Connector node should
-                                    expose to tailnet. If unset, none are exposed.
+                                    SubnetRouter defines subnet routes that the Connector device should
+                                    expose to tailnet as a Tailscale subnet router.
                                     https://tailscale.com/kb/1019/subnets/
+                                    If this field is unset, the device does not get configured as a Tailscale subnet router.
+                                    This field is mutually exclusive with the appConnector field.
                                 properties:
                                     advertiseRoutes:
                                         description: |-
@@ -151,8 +187,10 @@ spec:
                                 type: array
                         type: object
                         x-kubernetes-validations:
-                            - message: A Connector needs to be either an exit node or a subnet router, or both.
-                              rule: has(self.subnetRouter) || self.exitNode == true
+                            - message: A Connector needs to have at least one of exit node, subnet router or app connector configured.
+                              rule: has(self.subnetRouter) || (has(self.exitNode) && self.exitNode == true) || has(self.appConnector)
+                            - message: The appConnector field is mutually exclusive with exitNode and subnetRouter fields.
+                              rule: '!((has(self.subnetRouter) || (has(self.exitNode)  && self.exitNode == true)) && has(self.appConnector))'
                     status:
                         description: |-
                             ConnectorStatus describes the status of the Connector. This is set
@@ -225,6 +263,9 @@ spec:
                                     If MagicDNS is enabled in your tailnet, it is the MagicDNS name of the
                                     node.
                                 type: string
+                            isAppConnector:
+                                description: IsAppConnector is set to true if the Connector acts as an app connector.
+                                type: boolean
                             isExitNode:
                                 description: IsExitNode is set to true if the Connector acts as an exit node.
                                 type: boolean
@@ -253,7 +294,7 @@ apiVersion: apiextensions.k8s.io/v1
 kind: CustomResourceDefinition
 metadata:
     annotations:
-        controller-gen.kubebuilder.io/version: v0.15.1-0.20240618033008-7824932b0cab
+        controller-gen.kubebuilder.io/version: v0.17.0
     name: dnsconfigs.tailscale.com
 spec:
     group: tailscale.com
@@ -435,7 +476,7 @@ apiVersion: apiextensions.k8s.io/v1
 kind: CustomResourceDefinition
 metadata:
     annotations:
-        controller-gen.kubebuilder.io/version: v0.15.1-0.20240618033008-7824932b0cab
+        controller-gen.kubebuilder.io/version: v0.17.0
     name: proxyclasses.tailscale.com
 spec:
     group: tailscale.com
@@ -499,12 +540,48 @@ spec:
                                     enable:
                                         description: |-
                                             Setting enable to true will make the proxy serve Tailscale metrics
-                                            at <pod-ip>:9001/debug/metrics.
+                                            at <pod-ip>:9002/metrics.
+                                            A metrics Service named <proxy-statefulset>-metrics will also be created in the operator's namespace and will
+                                            serve the metrics at <service-ip>:9002/metrics.
+
+                                            In 1.78.x and 1.80.x, this field also serves as the default value for
+                                            .spec.statefulSet.pod.tailscaleContainer.debug.enable. From 1.82.0, both
+                                            fields will independently default to false.
+
                                             Defaults to false.
                                         type: boolean
+                                    serviceMonitor:
+                                        description: |-
+                                            Enable to create a Prometheus ServiceMonitor for scraping the proxy's Tailscale metrics.
+                                            The ServiceMonitor will select the metrics Service that gets created when metrics are enabled.
+                                            The ingested metrics for each Service monitor will have labels to identify the proxy:
+                                            ts_proxy_type: ingress_service|ingress_resource|connector|proxygroup
+                                            ts_proxy_parent_name: name of the parent resource (i.e name of the Connector, Tailscale Ingress, Tailscale Service or ProxyGroup)
+                                            ts_proxy_parent_namespace: namespace of the parent resource (if the parent resource is not cluster scoped)
+                                            job: ts_<proxy type>_[<parent namespace>]_<parent_name>
+                                        properties:
+                                            enable:
+                                                description: If Enable is set to true, a Prometheus ServiceMonitor will be created. Enable can only be set to true if metrics are enabled.
+                                                type: boolean
+                                            labels:
+                                                additionalProperties:
+                                                    maxLength: 63
+                                                    pattern: ^(([a-zA-Z0-9][-._a-zA-Z0-9]*)?[a-zA-Z0-9])?$
+                                                    type: string
+                                                description: |-
+                                                    Labels to add to the ServiceMonitor.
+                                                    Labels must be valid Kubernetes labels.
+                                                    https://kubernetes.io/docs/concepts/overview/working-with-objects/labels/#syntax-and-character-set
+                                                type: object
+                                        required:
+                                            - enable
+                                        type: object
                                 required:
                                     - enable
                                 type: object
+                                x-kubernetes-validations:
+                                    - message: ServiceMonitor can only be enabled if metrics are enabled
+                                      rule: '!(has(self.serviceMonitor) && self.serviceMonitor.enable  && !self.enable)'
                             statefulSet:
                                 description: |-
                                     Configuration parameters for the proxy's StatefulSet. Tailscale
@@ -525,6 +602,8 @@ spec:
                                         type: object
                                     labels:
                                         additionalProperties:
+                                            maxLength: 63
+                                            pattern: ^(([a-zA-Z0-9][-._a-zA-Z0-9]*)?[a-zA-Z0-9])?$
                                             type: string
                                         description: |-
                                             Labels that will be added to the StatefulSet created for the proxy.
@@ -807,7 +886,7 @@ spec:
                                                                                         pod labels will be ignored. The default value is empty.
                                                                                         The same key is forbidden to exist in both matchLabelKeys and labelSelector.
                                                                                         Also, matchLabelKeys cannot be set when labelSelector isn't set.
-                                                                                        This is an alpha field and requires enabling MatchLabelKeysInPodAffinity feature gate.
+                                                                                        This is a beta field and requires enabling MatchLabelKeysInPodAffinity feature gate (enabled by default).
                                                                                     items:
                                                                                         type: string
                                                                                     type: array
@@ -822,7 +901,7 @@ spec:
                                                                                         pod labels will be ignored. The default value is empty.
                                                                                         The same key is forbidden to exist in both mismatchLabelKeys and labelSelector.
                                                                                         Also, mismatchLabelKeys cannot be set when labelSelector isn't set.
-                                                                                        This is an alpha field and requires enabling MatchLabelKeysInPodAffinity feature gate.
+                                                                                        This is a beta field and requires enabling MatchLabelKeysInPodAffinity feature gate (enabled by default).
                                                                                     items:
                                                                                         type: string
                                                                                     type: array
@@ -983,7 +1062,7 @@ spec:
                                                                                 pod labels will be ignored. The default value is empty.
                                                                                 The same key is forbidden to exist in both matchLabelKeys and labelSelector.
                                                                                 Also, matchLabelKeys cannot be set when labelSelector isn't set.
-                                                                                This is an alpha field and requires enabling MatchLabelKeysInPodAffinity feature gate.
+                                                                                This is a beta field and requires enabling MatchLabelKeysInPodAffinity feature gate (enabled by default).
                                                                             items:
                                                                                 type: string
                                                                             type: array
@@ -998,7 +1077,7 @@ spec:
                                                                                 pod labels will be ignored. The default value is empty.
                                                                                 The same key is forbidden to exist in both mismatchLabelKeys and labelSelector.
                                                                                 Also, mismatchLabelKeys cannot be set when labelSelector isn't set.
-                                                                                This is an alpha field and requires enabling MatchLabelKeysInPodAffinity feature gate.
+                                                                                This is a beta field and requires enabling MatchLabelKeysInPodAffinity feature gate (enabled by default).
                                                                             items:
                                                                                 type: string
                                                                             type: array
@@ -1152,7 +1231,7 @@ spec:
                                                                                         pod labels will be ignored. The default value is empty.
                                                                                         The same key is forbidden to exist in both matchLabelKeys and labelSelector.
                                                                                         Also, matchLabelKeys cannot be set when labelSelector isn't set.
-                                                                                        This is an alpha field and requires enabling MatchLabelKeysInPodAffinity feature gate.
+                                                                                        This is a beta field and requires enabling MatchLabelKeysInPodAffinity feature gate (enabled by default).
                                                                                     items:
                                                                                         type: string
                                                                                     type: array
@@ -1167,7 +1246,7 @@ spec:
                                                                                         pod labels will be ignored. The default value is empty.
                                                                                         The same key is forbidden to exist in both mismatchLabelKeys and labelSelector.
                                                                                         Also, mismatchLabelKeys cannot be set when labelSelector isn't set.
-                                                                                        This is an alpha field and requires enabling MatchLabelKeysInPodAffinity feature gate.
+                                                                                        This is a beta field and requires enabling MatchLabelKeysInPodAffinity feature gate (enabled by default).
                                                                                     items:
                                                                                         type: string
                                                                                     type: array
@@ -1328,7 +1407,7 @@ spec:
                                                                                 pod labels will be ignored. The default value is empty.
                                                                                 The same key is forbidden to exist in both matchLabelKeys and labelSelector.
                                                                                 Also, matchLabelKeys cannot be set when labelSelector isn't set.
-                                                                                This is an alpha field and requires enabling MatchLabelKeysInPodAffinity feature gate.
+                                                                                This is a beta field and requires enabling MatchLabelKeysInPodAffinity feature gate (enabled by default).
                                                                             items:
                                                                                 type: string
                                                                             type: array
@@ -1343,7 +1422,7 @@ spec:
                                                                                 pod labels will be ignored. The default value is empty.
                                                                                 The same key is forbidden to exist in both mismatchLabelKeys and labelSelector.
                                                                                 Also, mismatchLabelKeys cannot be set when labelSelector isn't set.
-                                                                                This is an alpha field and requires enabling MatchLabelKeysInPodAffinity feature gate.
+                                                                                This is a beta field and requires enabling MatchLabelKeysInPodAffinity feature gate (enabled by default).
                                                                             items:
                                                                                 type: string
                                                                             type: array
@@ -1455,6 +1534,8 @@ spec:
                                                 type: array
                                             labels:
                                                 additionalProperties:
+                                                    maxLength: 63
+                                                    pattern: ^(([a-zA-Z0-9][-._a-zA-Z0-9]*)?[a-zA-Z0-9])?$
                                                     type: string
                                                 description: |-
                                                     Labels that will be added to the proxy Pod.
@@ -1560,6 +1641,32 @@ spec:
                                                             Note that this field cannot be set when spec.os.name is windows.
                                                         format: int64
                                                         type: integer
+                                                    seLinuxChangePolicy:
+                                                        description: |-
+                                                            seLinuxChangePolicy defines how the container's SELinux label is applied to all volumes used by the Pod.
+                                                            It has no effect on nodes that do not support SELinux or to volumes does not support SELinux.
+                                                            Valid values are "MountOption" and "Recursive".
+
+                                                            "Recursive" means relabeling of all files on all Pod volumes by the container runtime.
+                                                            This may be slow for large volumes, but allows mixing privileged and unprivileged Pods sharing the same volume on the same node.
+
+                                                            "MountOption" mounts all eligible Pod volumes with `-o context` mount option.
+                                                            This requires all Pods that share the same volume to use the same SELinux label.
+                                                            It is not possible to share the same volume among privileged and unprivileged Pods.
+                                                            Eligible volumes are in-tree FibreChannel and iSCSI volumes, and all CSI volumes
+                                                            whose CSI driver announces SELinux support by setting spec.seLinuxMount: true in their
+                                                            CSIDriver instance. Other volumes are always re-labelled recursively.
+                                                            "MountOption" value is allowed only when SELinuxMount feature gate is enabled.
+
+                                                            If not specified and SELinuxMount feature gate is enabled, "MountOption" is used.
+                                                            If not specified and SELinuxMount feature gate is disabled, "MountOption" is used for ReadWriteOncePod volumes
+                                                            and "Recursive" for all other volumes.
+
+                                                            This field affects only Pods that have SELinux label set, either in PodSecurityContext or in SecurityContext of all containers.
+
+                                                            All Pods that use the same volume should use the same seLinuxChangePolicy, otherwise some pods can get stuck in ContainerCreating state.
+                                                            Note that this field cannot be set when spec.os.name is windows.
+                                                        type: string
                                                     seLinuxOptions:
                                                         description: |-
                                                             The SELinux context to be applied to all containers.
@@ -1608,18 +1715,28 @@ spec:
                                                         type: object
                                                     supplementalGroups:
                                                         description: |-
-                                                            A list of groups applied to the first process run in each container, in addition
-                                                            to the container's primary GID, the fsGroup (if specified), and group memberships
-                                                            defined in the container image for the uid of the container process. If unspecified,
-                                                            no additional groups are added to any container. Note that group memberships
-                                                            defined in the container image for the uid of the container process are still effective,
-                                                            even if they are not included in this list.
+                                                            A list of groups applied to the first process run in each container, in
+                                                            addition to the container's primary GID and fsGroup (if specified).  If
+                                                            the SupplementalGroupsPolicy feature is enabled, the
+                                                            supplementalGroupsPolicy field determines whether these are in addition
+                                                            to or instead of any group memberships defined in the container image.
+                                                            If unspecified, no additional groups are added, though group memberships
+                                                            defined in the container image may still be used, depending on the
+                                                            supplementalGroupsPolicy field.
                                                             Note that this field cannot be set when spec.os.name is windows.
                                                         items:
                                                             format: int64
                                                             type: integer
                                                         type: array
                                                         x-kubernetes-list-type: atomic
+                                                    supplementalGroupsPolicy:
+                                                        description: |-
+                                                            Defines how supplemental groups of the first container processes are calculated.
+                                                            Valid values are "Merge" and "Strict". If not specified, "Merge" is used.
+                                                            (Alpha) Using the field requires the SupplementalGroupsPolicy feature gate to be enabled
+                                                            and the container runtime must implement support for this feature.
+                                                            Note that this field cannot be set when spec.os.name is windows.
+                                                        type: string
                                                     sysctls:
                                                         description: |-
                                                             Sysctls hold a list of namespaced sysctls used for the pod. Pods with unsupported
@@ -1675,6 +1792,25 @@ spec:
                                             tailscaleContainer:
                                                 description: Configuration for the proxy container running tailscale.
                                                 properties:
+                                                    debug:
+                                                        description: |-
+                                                            Configuration for enabling extra debug information in the container.
+                                                            Not recommended for production use.
+                                                        properties:
+                                                            enable:
+                                                                description: |-
+                                                                    Enable tailscaled's HTTP pprof endpoints at <pod-ip>:9001/debug/pprof/
+                                                                    and internal debug metrics endpoint at <pod-ip>:9001/debug/metrics, where
+                                                                    9001 is a container port named "debug". The endpoints and their responses
+                                                                    may change in backwards incompatible ways in the future, and should not
+                                                                    be considered stable.
+
+                                                                    In 1.78.x and 1.80.x, this setting will default to the value of
+                                                                    .spec.metrics.enable, and requests to the "metrics" port matching the
+                                                                    mux pattern /debug/ will be forwarded to the "debug" port. In 1.82.x,
+                                                                    this setting will default to false, and no requests will be proxied.
+                                                                type: boolean
+                                                        type: object
                                                     env:
                                                         description: |-
                                                             List of environment variables to set in the container.
@@ -1751,6 +1887,12 @@ spec:
                                                                                 the Pod where this field is used. It makes that resource available
                                                                                 inside a container.
                                                                             type: string
+                                                                        request:
+                                                                            description: |-
+                                                                                Request is the name chosen for a request in the referenced claim.
+                                                                                If empty, everything from the claim is made available, otherwise
+                                                                                only the result of this request.
+                                                                            type: string
                                                                     required:
                                                                         - name
                                                                     type: object
@@ -1786,11 +1928,12 @@ spec:
                                                     securityContext:
                                                         description: |-
                                                             Container security context.
-                                                            Security context specified here will override the security context by the operator.
-                                                            By default the operator:
-                                                            - sets 'privileged: true' for the init container
-                                                            - set NET_ADMIN capability for tailscale container for proxies that
-                                                            are created for Services or Connector.
+                                                            Security context specified here will override the security context set by the operator.
+                                                            By default the operator sets the Tailscale container and the Tailscale init container to privileged
+                                                            for proxies created for Tailscale ingress and egress Service, Connector and ProxyGroup.
+                                                            You can reduce the permissions of the Tailscale container to cap NET_ADMIN by
+                                                            installing device plugin in your cluster and configuring the proxies tun device to be created
+                                                            by the device plugin, see  https://github.com/tailscale/tailscale/issues/10814#issuecomment-2479977752
                                                             https://kubernetes.io/docs/reference/kubernetes-api/workload-resources/pod-v1/#security-context
                                                         properties:
                                                             allowPrivilegeEscalation:
@@ -1858,7 +2001,7 @@ spec:
                                                             procMount:
                                                                 description: |-
                                                                     procMount denotes the type of proc mount to use for the containers.
-                                                                    The default is DefaultProcMount which uses the container runtime defaults for
+                                                                    The default value is Default which uses the container runtime defaults for
                                                                     readonly paths and masked paths.
                                                                     This requires the ProcMountType feature flag to be enabled.
                                                                     Note that this field cannot be set when spec.os.name is windows.
@@ -1979,6 +2122,25 @@ spec:
                                             tailscaleInitContainer:
                                                 description: Configuration for the proxy init container that enables forwarding.
                                                 properties:
+                                                    debug:
+                                                        description: |-
+                                                            Configuration for enabling extra debug information in the container.
+                                                            Not recommended for production use.
+                                                        properties:
+                                                            enable:
+                                                                description: |-
+                                                                    Enable tailscaled's HTTP pprof endpoints at <pod-ip>:9001/debug/pprof/
+                                                                    and internal debug metrics endpoint at <pod-ip>:9001/debug/metrics, where
+                                                                    9001 is a container port named "debug". The endpoints and their responses
+                                                                    may change in backwards incompatible ways in the future, and should not
+                                                                    be considered stable.
+
+                                                                    In 1.78.x and 1.80.x, this setting will default to the value of
+                                                                    .spec.metrics.enable, and requests to the "metrics" port matching the
+                                                                    mux pattern /debug/ will be forwarded to the "debug" port. In 1.82.x,
+                                                                    this setting will default to false, and no requests will be proxied.
+                                                                type: boolean
+                                                        type: object
                                                     env:
                                                         description: |-
                                                             List of environment variables to set in the container.
@@ -2055,6 +2217,12 @@ spec:
                                                                                 the Pod where this field is used. It makes that resource available
                                                                                 inside a container.
                                                                             type: string
+                                                                        request:
+                                                                            description: |-
+                                                                                Request is the name chosen for a request in the referenced claim.
+                                                                                If empty, everything from the claim is made available, otherwise
+                                                                                only the result of this request.
+                                                                            type: string
                                                                     required:
                                                                         - name
                                                                     type: object
@@ -2090,11 +2258,12 @@ spec:
                                                     securityContext:
                                                         description: |-
                                                             Container security context.
-                                                            Security context specified here will override the security context by the operator.
-                                                            By default the operator:
-                                                            - sets 'privileged: true' for the init container
-                                                            - set NET_ADMIN capability for tailscale container for proxies that
-                                                            are created for Services or Connector.
+                                                            Security context specified here will override the security context set by the operator.
+                                                            By default the operator sets the Tailscale container and the Tailscale init container to privileged
+                                                            for proxies created for Tailscale ingress and egress Service, Connector and ProxyGroup.
+                                                            You can reduce the permissions of the Tailscale container to cap NET_ADMIN by
+                                                            installing device plugin in your cluster and configuring the proxies tun device to be created
+                                                            by the device plugin, see  https://github.com/tailscale/tailscale/issues/10814#issuecomment-2479977752
                                                             https://kubernetes.io/docs/reference/kubernetes-api/workload-resources/pod-v1/#security-context
                                                         properties:
                                                             allowPrivilegeEscalation:
@@ -2162,7 +2331,7 @@ spec:
                                                             procMount:
                                                                 description: |-
                                                                     procMount denotes the type of proc mount to use for the containers.
-                                                                    The default is DefaultProcMount which uses the container runtime defaults for
+                                                                    The default value is Default which uses the container runtime defaults for
                                                                     readonly paths and masked paths.
                                                                     This requires the ProcMountType feature flag to be enabled.
                                                                     Note that this field cannot be set when spec.os.name is windows.
@@ -2596,7 +2765,7 @@ apiVersion: apiextensions.k8s.io/v1
 kind: CustomResourceDefinition
 metadata:
     annotations:
-        controller-gen.kubebuilder.io/version: v0.15.1-0.20240618033008-7824932b0cab
+        controller-gen.kubebuilder.io/version: v0.17.0
     name: proxygroups.tailscale.com
 spec:
     group: tailscale.com
@@ -2614,9 +2783,24 @@ spec:
               jsonPath: .status.conditions[?(@.type == "ProxyGroupReady")].reason
               name: Status
               type: string
+            - description: ProxyGroup type.
+              jsonPath: .spec.type
+              name: Type
+              type: string
           name: v1alpha1
           schema:
             openAPIV3Schema:
+                description: |-
+                    ProxyGroup defines a set of Tailscale devices that will act as proxies.
+                    Currently only egress ProxyGroups are supported.
+
+                    Use the tailscale.com/proxy-group annotation on a Service to specify that
+                    the egress proxy should be implemented by a ProxyGroup instead of a single
+                    dedicated proxy. In addition to running a highly available set of proxies,
+                    ProxyGroup also allows for serving many annotated Services from a single
+                    set of proxies to minimise resource consumption.
+
+                    More info: https://tailscale.com/kb/1438/kubernetes-operator-cluster-egress
                 properties:
                     apiVersion:
                         description: |-
@@ -2660,6 +2844,7 @@ spec:
                                     Replicas specifies how many replicas to create the StatefulSet with.
                                     Defaults to 2.
                                 format: int32
+                                minimum: 0
                                 type: integer
                             tags:
                                 description: |-
@@ -2674,10 +2859,16 @@ spec:
                                     type: string
                                 type: array
                             type:
-                                description: Type of the ProxyGroup proxies. Currently the only supported type is egress.
+                                description: |-
+                                    Type of the ProxyGroup proxies. Supported types are egress and ingress.
+                                    Type is immutable once a ProxyGroup is created.
                                 enum:
                                     - egress
+                                    - ingress
                                 type: string
+                                x-kubernetes-validations:
+                                    - message: ProxyGroup type is immutable
+                                      rule: self == oldSelf
                         required:
                             - type
                         type: object
@@ -2784,7 +2975,7 @@ apiVersion: apiextensions.k8s.io/v1
 kind: CustomResourceDefinition
 metadata:
     annotations:
-        controller-gen.kubebuilder.io/version: v0.15.1-0.20240618033008-7824932b0cab
+        controller-gen.kubebuilder.io/version: v0.17.0
     name: recorders.tailscale.com
 spec:
     group: tailscale.com
@@ -2809,6 +3000,12 @@ spec:
           name: v1alpha1
           schema:
             openAPIV3Schema:
+                description: |-
+                    Recorder defines a tsrecorder device for recording SSH sessions. By default,
+                    it will store recordings in a local ephemeral volume. If you want to persist
+                    recordings, you can configure an S3-compatible API for storage.
+
+                    More info: https://tailscale.com/kb/1484/kubernetes-operator-deploying-tsrecorder
                 properties:
                     apiVersion:
                         description: |-
@@ -3132,7 +3329,7 @@ spec:
                                                                                         pod labels will be ignored. The default value is empty.
                                                                                         The same key is forbidden to exist in both matchLabelKeys and labelSelector.
                                                                                         Also, matchLabelKeys cannot be set when labelSelector isn't set.
-                                                                                        This is an alpha field and requires enabling MatchLabelKeysInPodAffinity feature gate.
+                                                                                        This is a beta field and requires enabling MatchLabelKeysInPodAffinity feature gate (enabled by default).
                                                                                     items:
                                                                                         type: string
                                                                                     type: array
@@ -3147,7 +3344,7 @@ spec:
                                                                                         pod labels will be ignored. The default value is empty.
                                                                                         The same key is forbidden to exist in both mismatchLabelKeys and labelSelector.
                                                                                         Also, mismatchLabelKeys cannot be set when labelSelector isn't set.
-                                                                                        This is an alpha field and requires enabling MatchLabelKeysInPodAffinity feature gate.
+                                                                                        This is a beta field and requires enabling MatchLabelKeysInPodAffinity feature gate (enabled by default).
                                                                                     items:
                                                                                         type: string
                                                                                     type: array
@@ -3308,7 +3505,7 @@ spec:
                                                                                 pod labels will be ignored. The default value is empty.
                                                                                 The same key is forbidden to exist in both matchLabelKeys and labelSelector.
                                                                                 Also, matchLabelKeys cannot be set when labelSelector isn't set.
-                                                                                This is an alpha field and requires enabling MatchLabelKeysInPodAffinity feature gate.
+                                                                                This is a beta field and requires enabling MatchLabelKeysInPodAffinity feature gate (enabled by default).
                                                                             items:
                                                                                 type: string
                                                                             type: array
@@ -3323,7 +3520,7 @@ spec:
                                                                                 pod labels will be ignored. The default value is empty.
                                                                                 The same key is forbidden to exist in both mismatchLabelKeys and labelSelector.
                                                                                 Also, mismatchLabelKeys cannot be set when labelSelector isn't set.
-                                                                                This is an alpha field and requires enabling MatchLabelKeysInPodAffinity feature gate.
+                                                                                This is a beta field and requires enabling MatchLabelKeysInPodAffinity feature gate (enabled by default).
                                                                             items:
                                                                                 type: string
                                                                             type: array
@@ -3477,7 +3674,7 @@ spec:
                                                                                         pod labels will be ignored. The default value is empty.
                                                                                         The same key is forbidden to exist in both matchLabelKeys and labelSelector.
                                                                                         Also, matchLabelKeys cannot be set when labelSelector isn't set.
-                                                                                        This is an alpha field and requires enabling MatchLabelKeysInPodAffinity feature gate.
+                                                                                        This is a beta field and requires enabling MatchLabelKeysInPodAffinity feature gate (enabled by default).
                                                                                     items:
                                                                                         type: string
                                                                                     type: array
@@ -3492,7 +3689,7 @@ spec:
                                                                                         pod labels will be ignored. The default value is empty.
                                                                                         The same key is forbidden to exist in both mismatchLabelKeys and labelSelector.
                                                                                         Also, mismatchLabelKeys cannot be set when labelSelector isn't set.
-                                                                                        This is an alpha field and requires enabling MatchLabelKeysInPodAffinity feature gate.
+                                                                                        This is a beta field and requires enabling MatchLabelKeysInPodAffinity feature gate (enabled by default).
                                                                                     items:
                                                                                         type: string
                                                                                     type: array
@@ -3653,7 +3850,7 @@ spec:
                                                                                 pod labels will be ignored. The default value is empty.
                                                                                 The same key is forbidden to exist in both matchLabelKeys and labelSelector.
                                                                                 Also, matchLabelKeys cannot be set when labelSelector isn't set.
-                                                                                This is an alpha field and requires enabling MatchLabelKeysInPodAffinity feature gate.
+                                                                                This is a beta field and requires enabling MatchLabelKeysInPodAffinity feature gate (enabled by default).
                                                                             items:
                                                                                 type: string
                                                                             type: array
@@ -3668,7 +3865,7 @@ spec:
                                                                                 pod labels will be ignored. The default value is empty.
                                                                                 The same key is forbidden to exist in both mismatchLabelKeys and labelSelector.
                                                                                 Also, mismatchLabelKeys cannot be set when labelSelector isn't set.
-                                                                                This is an alpha field and requires enabling MatchLabelKeysInPodAffinity feature gate.
+                                                                                This is a beta field and requires enabling MatchLabelKeysInPodAffinity feature gate (enabled by default).
                                                                             items:
                                                                                 type: string
                                                                             type: array
@@ -3830,6 +4027,12 @@ spec:
                                                                                 the Pod where this field is used. It makes that resource available
                                                                                 inside a container.
                                                                             type: string
+                                                                        request:
+                                                                            description: |-
+                                                                                Request is the name chosen for a request in the referenced claim.
+                                                                                If empty, everything from the claim is made available, otherwise
+                                                                                only the result of this request.
+                                                                            type: string
                                                                     required:
                                                                         - name
                                                                     type: object
@@ -3933,7 +4136,7 @@ spec:
                                                             procMount:
                                                                 description: |-
                                                                     procMount denotes the type of proc mount to use for the containers.
-                                                                    The default is DefaultProcMount which uses the container runtime defaults for
+                                                                    The default value is Default which uses the container runtime defaults for
                                                                     readonly paths and masked paths.
                                                                     This requires the ProcMountType feature flag to be enabled.
                                                                     Note that this field cannot be set when spec.os.name is windows.
@@ -4170,6 +4373,32 @@ spec:
                                                             Note that this field cannot be set when spec.os.name is windows.
                                                         format: int64
                                                         type: integer
+                                                    seLinuxChangePolicy:
+                                                        description: |-
+                                                            seLinuxChangePolicy defines how the container's SELinux label is applied to all volumes used by the Pod.
+                                                            It has no effect on nodes that do not support SELinux or to volumes does not support SELinux.
+                                                            Valid values are "MountOption" and "Recursive".
+
+                                                            "Recursive" means relabeling of all files on all Pod volumes by the container runtime.
+                                                            This may be slow for large volumes, but allows mixing privileged and unprivileged Pods sharing the same volume on the same node.
+
+                                                            "MountOption" mounts all eligible Pod volumes with `-o context` mount option.
+                                                            This requires all Pods that share the same volume to use the same SELinux label.
+                                                            It is not possible to share the same volume among privileged and unprivileged Pods.
+                                                            Eligible volumes are in-tree FibreChannel and iSCSI volumes, and all CSI volumes
+                                                            whose CSI driver announces SELinux support by setting spec.seLinuxMount: true in their
+                                                            CSIDriver instance. Other volumes are always re-labelled recursively.
+                                                            "MountOption" value is allowed only when SELinuxMount feature gate is enabled.
+
+                                                            If not specified and SELinuxMount feature gate is enabled, "MountOption" is used.
+                                                            If not specified and SELinuxMount feature gate is disabled, "MountOption" is used for ReadWriteOncePod volumes
+                                                            and "Recursive" for all other volumes.
+
+                                                            This field affects only Pods that have SELinux label set, either in PodSecurityContext or in SecurityContext of all containers.
+
+                                                            All Pods that use the same volume should use the same seLinuxChangePolicy, otherwise some pods can get stuck in ContainerCreating state.
+                                                            Note that this field cannot be set when spec.os.name is windows.
+                                                        type: string
                                                     seLinuxOptions:
                                                         description: |-
                                                             The SELinux context to be applied to all containers.
@@ -4218,18 +4447,28 @@ spec:
                                                         type: object
                                                     supplementalGroups:
                                                         description: |-
-                                                            A list of groups applied to the first process run in each container, in addition
-                                                            to the container's primary GID, the fsGroup (if specified), and group memberships
-                                                            defined in the container image for the uid of the container process. If unspecified,
-                                                            no additional groups are added to any container. Note that group memberships
-                                                            defined in the container image for the uid of the container process are still effective,
-                                                            even if they are not included in this list.
+                                                            A list of groups applied to the first process run in each container, in
+                                                            addition to the container's primary GID and fsGroup (if specified).  If
+                                                            the SupplementalGroupsPolicy feature is enabled, the
+                                                            supplementalGroupsPolicy field determines whether these are in addition
+                                                            to or instead of any group memberships defined in the container image.
+                                                            If unspecified, no additional groups are added, though group memberships
+                                                            defined in the container image may still be used, depending on the
+                                                            supplementalGroupsPolicy field.
                                                             Note that this field cannot be set when spec.os.name is windows.
                                                         items:
                                                             format: int64
                                                             type: integer
                                                         type: array
                                                         x-kubernetes-list-type: atomic
+                                                    supplementalGroupsPolicy:
+                                                        description: |-
+                                                            Defines how supplemental groups of the first container processes are calculated.
+                                                            Valid values are "Merge" and "Strict". If not specified, "Merge" is used.
+                                                            (Alpha) Using the field requires the SupplementalGroupsPolicy feature gate to be enabled
+                                                            and the container runtime must implement support for this feature.
+                                                            Note that this field cannot be set when spec.os.name is windows.
+                                                        type: string
                                                     sysctls:
                                                         description: |-
                                                             Sysctls hold a list of namespaced sysctls used for the pod. Pods with unsupported
@@ -4562,6 +4801,16 @@ rules:
         - list
         - watch
         - update
+    - apiGroups:
+        - apiextensions.k8s.io
+      resourceNames:
+        - servicemonitors.monitoring.coreos.com
+      resources:
+        - customresourcedefinitions
+      verbs:
+        - get
+        - list
+        - watch
 ---
 apiVersion: rbac.authorization.k8s.io/v1
 kind: ClusterRoleBinding
@@ -4642,6 +4891,16 @@ rules:
         - update
         - list
         - watch
+    - apiGroups:
+        - monitoring.coreos.com
+      resources:
+        - servicemonitors
+      verbs:
+        - get
+        - list
+        - update
+        - create
+        - delete
 ---
 apiVersion: rbac.authorization.k8s.io/v1
 kind: Role
@@ -4662,6 +4921,14 @@ rules:
         - patch
         - update
         - watch
+    - apiGroups:
+        - ""
+      resources:
+        - events
+      verbs:
+        - create
+        - patch
+        - get
 ---
 apiVersion: rbac.authorization.k8s.io/v1
 kind: RoleBinding
@@ -4734,6 +5001,14 @@ spec:
                       value: "false"
                     - name: PROXY_FIREWALL_MODE
                       value: auto
+                    - name: POD_NAME
+                      valueFrom:
+                        fieldRef:
+                            fieldPath: metadata.name
+                    - name: POD_UID
+                      valueFrom:
+                        fieldRef:
+                            fieldPath: metadata.uid
                   image: tailscale/k8s-operator:unstable
                   imagePullPolicy: Always
                   name: operator

cmd/k8s-operator/deploy/manifests/proxy.yaml

@@ -30,7 +30,13 @@ spec:
               valueFrom:
                 fieldRef:
                   fieldPath: status.podIP
+            - name: POD_NAME
+              valueFrom:
+                fieldRef:
+                  fieldPath: metadata.name
+            - name: POD_UID
+              valueFrom:
+                fieldRef:
+                  fieldPath: metadata.uid
           securityContext:
-            capabilities:
-              add:
-                - NET_ADMIN
+            privileged: true

cmd/k8s-operator/deploy/manifests/userspace-proxy.yaml

@@ -24,3 +24,11 @@ spec:
               valueFrom:
                 fieldRef:
                   fieldPath: status.podIP
+            - name: POD_NAME
+              valueFrom:
+                fieldRef:
+                  fieldPath: metadata.name
+            - name: POD_UID
+              valueFrom:
+                fieldRef:
+                  fieldPath: metadata.uid

cmd/k8s-operator/dnsrecords.go

@@ -10,6 +10,7 @@ import (
 	"encoding/json"
 	"fmt"
 	"slices"
+	"strings"
 
 	"go.uber.org/zap"
 	corev1 "k8s.io/api/core/v1"
@@ -98,7 +99,15 @@ func (dnsRR *dnsRecordsReconciler) Reconcile(ctx context.Context, req reconcile.
 		return reconcile.Result{}, nil
 	}
 
-	return reconcile.Result{}, dnsRR.maybeProvision(ctx, headlessSvc, logger)
+	if err := dnsRR.maybeProvision(ctx, headlessSvc, logger); err != nil {
+		if strings.Contains(err.Error(), optimisticLockErrorMsg) {
+			logger.Infof("optimistic lock error, retrying: %s", err)
+		} else {
+			return reconcile.Result{}, err
+		}
+	}
+
+	return reconcile.Result{}, nil
 }
 
 // maybeProvision ensures that dnsrecords ConfigMap contains a record for the

cmd/k8s-operator/e2e/ingress_test.go

@@ -0,0 +1,108 @@
+// Copyright (c) Tailscale Inc & AUTHORS
+// SPDX-License-Identifier: BSD-3-Clause
+
+package e2e
+
+import (
+	"context"
+	"fmt"
+	"net/http"
+	"testing"
+	"time"
+
+	corev1 "k8s.io/api/core/v1"
+	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
+	"k8s.io/apimachinery/pkg/util/wait"
+	"sigs.k8s.io/controller-runtime/pkg/client"
+	"sigs.k8s.io/controller-runtime/pkg/client/config"
+	kube "tailscale.com/k8s-operator"
+	"tailscale.com/tstest"
+)
+
+// See [TestMain] for test requirements.
+func TestIngress(t *testing.T) {
+	if tsClient == nil {
+		t.Skip("TestIngress requires credentials for a tailscale client")
+	}
+
+	ctx := context.Background()
+	cfg := config.GetConfigOrDie()
+	cl, err := client.New(cfg, client.Options{})
+	if err != nil {
+		t.Fatal(err)
+	}
+	// Apply nginx
+	createAndCleanup(t, ctx, cl, &corev1.Pod{
+		ObjectMeta: metav1.ObjectMeta{
+			Name:      "nginx",
+			Namespace: "default",
+			Labels: map[string]string{
+				"app.kubernetes.io/name": "nginx",
+			},
+		},
+		Spec: corev1.PodSpec{
+			Containers: []corev1.Container{
+				{
+					Name:  "nginx",
+					Image: "nginx",
+				},
+			},
+		},
+	})
+	// Apply service to expose it as ingress
+	svc := &corev1.Service{
+		ObjectMeta: metav1.ObjectMeta{
+			Name:      "test-ingress",
+			Namespace: "default",
+			Annotations: map[string]string{
+				"tailscale.com/expose": "true",
+			},
+		},
+		Spec: corev1.ServiceSpec{
+			Selector: map[string]string{
+				"app.kubernetes.io/name": "nginx",
+			},
+			Ports: []corev1.ServicePort{
+				{
+					Name:     "http",
+					Protocol: "TCP",
+					Port:     80,
+				},
+			},
+		},
+	}
+	createAndCleanup(t, ctx, cl, svc)
+
+	// TODO: instead of timing out only when test times out, cancel context after 60s or so.
+	if err := wait.PollUntilContextCancel(ctx, time.Millisecond*100, true, func(ctx context.Context) (done bool, err error) {
+		maybeReadySvc := &corev1.Service{ObjectMeta: objectMeta("default", "test-ingress")}
+		if err := get(ctx, cl, maybeReadySvc); err != nil {
+			return false, err
+		}
+		isReady := kube.SvcIsReady(maybeReadySvc)
+		if isReady {
+			t.Log("Service is ready")
+		}
+		return isReady, nil
+	}); err != nil {
+		t.Fatalf("error waiting for the Service to become Ready: %v", err)
+	}
+
+	var resp *http.Response
+	if err := tstest.WaitFor(time.Second*60, func() error {
+		// TODO(tomhjp): Get the tailnet DNS name from the associated secret instead.
+		// If we are not the first tailnet node with the requested name, we'll get
+		// a -N suffix.
+		resp, err = tsClient.HTTPClient.Get(fmt.Sprintf("http://%s-%s:80", svc.Namespace, svc.Name))
+		if err != nil {
+			return err
+		}
+		return nil
+	}); err != nil {
+		t.Fatalf("error trying to reach service: %v", err)
+	}
+
+	if resp.StatusCode != http.StatusOK {
+		t.Fatalf("unexpected status: %v; response body s", resp.StatusCode)
+	}
+}

cmd/k8s-operator/e2e/main_test.go

@@ -0,0 +1,194 @@
+// Copyright (c) Tailscale Inc & AUTHORS
+// SPDX-License-Identifier: BSD-3-Clause
+
+package e2e
+
+import (
+	"context"
+	"errors"
+	"fmt"
+	"log"
+	"os"
+	"slices"
+	"strings"
+	"testing"
+
+	"github.com/go-logr/zapr"
+	"github.com/tailscale/hujson"
+	"go.uber.org/zap/zapcore"
+	"golang.org/x/oauth2/clientcredentials"
+	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
+	"sigs.k8s.io/controller-runtime/pkg/client"
+	logf "sigs.k8s.io/controller-runtime/pkg/log"
+	kzap "sigs.k8s.io/controller-runtime/pkg/log/zap"
+	"tailscale.com/client/tailscale"
+)
+
+const (
+	e2eManagedComment = "// This is managed by the k8s-operator e2e tests"
+)
+
+var (
+	tsClient   *tailscale.Client
+	testGrants = map[string]string{
+		"test-proxy": `{
+			"src": ["tag:e2e-test-proxy"],
+			"dst": ["tag:k8s-operator"],
+			"app": {
+				"tailscale.com/cap/kubernetes": [{
+					"impersonate": {
+						"groups": ["ts:e2e-test-proxy"],
+					},
+				}],
+			},
+		}`,
+	}
+)
+
+// This test suite is currently not run in CI.
+// It requires some setup not handled by this code:
+// - Kubernetes cluster with tailscale operator installed
+// - Current kubeconfig context set to connect to that cluster (directly, no operator proxy)
+// - Operator installed with --set apiServerProxyConfig.mode="true"
+// - ACLs that define tag:e2e-test-proxy tag. TODO(tomhjp): Can maybe replace this prereq onwards with an API key
+// - OAuth client ID and secret in TS_API_CLIENT_ID and TS_API_CLIENT_SECRET env
+// - OAuth client must have auth_keys and policy_file write for tag:e2e-test-proxy tag
+func TestMain(m *testing.M) {
+	code, err := runTests(m)
+	if err != nil {
+		log.Fatal(err)
+	}
+	os.Exit(code)
+}
+
+func runTests(m *testing.M) (int, error) {
+	zlog := kzap.NewRaw([]kzap.Opts{kzap.UseDevMode(true), kzap.Level(zapcore.DebugLevel)}...).Sugar()
+	logf.SetLogger(zapr.NewLogger(zlog.Desugar()))
+	tailscale.I_Acknowledge_This_API_Is_Unstable = true
+
+	if clientID := os.Getenv("TS_API_CLIENT_ID"); clientID != "" {
+		cleanup, err := setupClientAndACLs()
+		if err != nil {
+			return 0, err
+		}
+		defer func() {
+			err = errors.Join(err, cleanup())
+		}()
+	}
+
+	return m.Run(), nil
+}
+
+func setupClientAndACLs() (cleanup func() error, _ error) {
+	ctx := context.Background()
+	credentials := clientcredentials.Config{
+		ClientID:     os.Getenv("TS_API_CLIENT_ID"),
+		ClientSecret: os.Getenv("TS_API_CLIENT_SECRET"),
+		TokenURL:     "https://login.tailscale.com/api/v2/oauth/token",
+		Scopes:       []string{"auth_keys", "policy_file"},
+	}
+	tsClient = tailscale.NewClient("-", nil)
+	tsClient.HTTPClient = credentials.Client(ctx)
+
+	if err := patchACLs(ctx, tsClient, func(acls *hujson.Value) {
+		for test, grant := range testGrants {
+			deleteTestGrants(test, acls)
+			addTestGrant(test, grant, acls)
+		}
+	}); err != nil {
+		return nil, err
+	}
+
+	return func() error {
+		return patchACLs(ctx, tsClient, func(acls *hujson.Value) {
+			for test := range testGrants {
+				deleteTestGrants(test, acls)
+			}
+		})
+	}, nil
+}
+
+func patchACLs(ctx context.Context, tsClient *tailscale.Client, patchFn func(*hujson.Value)) error {
+	acls, err := tsClient.ACLHuJSON(ctx)
+	if err != nil {
+		return err
+	}
+	hj, err := hujson.Parse([]byte(acls.ACL))
+	if err != nil {
+		return err
+	}
+
+	patchFn(&hj)
+
+	hj.Format()
+	acls.ACL = hj.String()
+	if _, err := tsClient.SetACLHuJSON(ctx, *acls, true); err != nil {
+		return err
+	}
+
+	return nil
+}
+
+func addTestGrant(test, grant string, acls *hujson.Value) error {
+	v, err := hujson.Parse([]byte(grant))
+	if err != nil {
+		return err
+	}
+
+	// Add the managed comment to the first line of the grant object contents.
+	v.Value.(*hujson.Object).Members[0].Name.BeforeExtra = hujson.Extra(fmt.Sprintf("%s: %s\n", e2eManagedComment, test))
+
+	if err := acls.Patch([]byte(fmt.Sprintf(`[{"op": "add", "path": "/grants/-", "value": %s}]`, v.String()))); err != nil {
+		return err
+	}
+
+	return nil
+}
+
+func deleteTestGrants(test string, acls *hujson.Value) error {
+	grants := acls.Find("/grants")
+
+	var patches []string
+	for i, g := range grants.Value.(*hujson.Array).Elements {
+		members := g.Value.(*hujson.Object).Members
+		if len(members) == 0 {
+			continue
+		}
+		comment := strings.TrimSpace(string(members[0].Name.BeforeExtra))
+		if name, found := strings.CutPrefix(comment, e2eManagedComment+": "); found && name == test {
+			patches = append(patches, fmt.Sprintf(`{"op": "remove", "path": "/grants/%d"}`, i))
+		}
+	}
+
+	// Remove in reverse order so we don't affect the found indices as we mutate.
+	slices.Reverse(patches)
+
+	if err := acls.Patch([]byte(fmt.Sprintf("[%s]", strings.Join(patches, ",")))); err != nil {
+		return err
+	}
+
+	return nil
+}
+
+func objectMeta(namespace, name string) metav1.ObjectMeta {
+	return metav1.ObjectMeta{
+		Namespace: namespace,
+		Name:      name,
+	}
+}
+
+func createAndCleanup(t *testing.T, ctx context.Context, cl client.Client, obj client.Object) {
+	t.Helper()
+	if err := cl.Create(ctx, obj); err != nil {
+		t.Fatal(err)
+	}
+	t.Cleanup(func() {
+		if err := cl.Delete(ctx, obj); err != nil {
+			t.Errorf("error cleaning up %s %s/%s: %s", obj.GetObjectKind().GroupVersionKind(), obj.GetNamespace(), obj.GetName(), err)
+		}
+	})
+}
+
+func get(ctx context.Context, cl client.Client, obj client.Object) error {
+	return cl.Get(ctx, client.ObjectKeyFromObject(obj), obj)
+}

cmd/k8s-operator/e2e/proxy_test.go

@@ -0,0 +1,156 @@
+// Copyright (c) Tailscale Inc & AUTHORS
+// SPDX-License-Identifier: BSD-3-Clause
+
+package e2e
+
+import (
+	"context"
+	"encoding/json"
+	"fmt"
+	"strings"
+	"testing"
+	"time"
+
+	corev1 "k8s.io/api/core/v1"
+	rbacv1 "k8s.io/api/rbac/v1"
+	apierrors "k8s.io/apimachinery/pkg/api/errors"
+	"k8s.io/client-go/rest"
+	"sigs.k8s.io/controller-runtime/pkg/client"
+	"sigs.k8s.io/controller-runtime/pkg/client/config"
+	"tailscale.com/client/tailscale"
+	"tailscale.com/tsnet"
+	"tailscale.com/tstest"
+)
+
+// See [TestMain] for test requirements.
+func TestProxy(t *testing.T) {
+	if tsClient == nil {
+		t.Skip("TestProxy requires credentials for a tailscale client")
+	}
+
+	ctx := context.Background()
+	cfg := config.GetConfigOrDie()
+	cl, err := client.New(cfg, client.Options{})
+	if err != nil {
+		t.Fatal(err)
+	}
+
+	// Create role and role binding to allow a group we'll impersonate to do stuff.
+	createAndCleanup(t, ctx, cl, &rbacv1.Role{
+		ObjectMeta: objectMeta("tailscale", "read-secrets"),
+		Rules: []rbacv1.PolicyRule{{
+			APIGroups: []string{""},
+			Verbs:     []string{"get"},
+			Resources: []string{"secrets"},
+		}},
+	})
+	createAndCleanup(t, ctx, cl, &rbacv1.RoleBinding{
+		ObjectMeta: objectMeta("tailscale", "read-secrets"),
+		Subjects: []rbacv1.Subject{{
+			Kind: "Group",
+			Name: "ts:e2e-test-proxy",
+		}},
+		RoleRef: rbacv1.RoleRef{
+			Kind: "Role",
+			Name: "read-secrets",
+		},
+	})
+
+	// Get operator host name from kube secret.
+	operatorSecret := corev1.Secret{
+		ObjectMeta: objectMeta("tailscale", "operator"),
+	}
+	if err := get(ctx, cl, &operatorSecret); err != nil {
+		t.Fatal(err)
+	}
+
+	// Connect to tailnet with test-specific tag so we can use the
+	// [testGrants] ACLs when connecting to the API server proxy
+	ts := tsnetServerWithTag(t, ctx, "tag:e2e-test-proxy")
+	proxyCfg := &rest.Config{
+		Host: fmt.Sprintf("https://%s:443", hostNameFromOperatorSecret(t, operatorSecret)),
+		Dial: ts.Dial,
+	}
+	proxyCl, err := client.New(proxyCfg, client.Options{})
+	if err != nil {
+		t.Fatal(err)
+	}
+
+	// Expect success.
+	allowedSecret := corev1.Secret{
+		ObjectMeta: objectMeta("tailscale", "operator"),
+	}
+	// Wait for up to a minute the first time we use the proxy, to give it time
+	// to provision the TLS certs.
+	if err := tstest.WaitFor(time.Second*60, func() error {
+		return get(ctx, proxyCl, &allowedSecret)
+	}); err != nil {
+		t.Fatal(err)
+	}
+
+	// Expect forbidden.
+	forbiddenSecret := corev1.Secret{
+		ObjectMeta: objectMeta("default", "operator"),
+	}
+	if err := get(ctx, proxyCl, &forbiddenSecret); err == nil || !apierrors.IsForbidden(err) {
+		t.Fatalf("expected forbidden error fetching secret from default namespace: %s", err)
+	}
+}
+
+func tsnetServerWithTag(t *testing.T, ctx context.Context, tag string) *tsnet.Server {
+	caps := tailscale.KeyCapabilities{
+		Devices: tailscale.KeyDeviceCapabilities{
+			Create: tailscale.KeyDeviceCreateCapabilities{
+				Reusable:      false,
+				Preauthorized: true,
+				Ephemeral:     true,
+				Tags:          []string{tag},
+			},
+		},
+	}
+
+	authKey, authKeyMeta, err := tsClient.CreateKey(ctx, caps)
+	if err != nil {
+		t.Fatal(err)
+	}
+	t.Cleanup(func() {
+		if err := tsClient.DeleteKey(ctx, authKeyMeta.ID); err != nil {
+			t.Errorf("error deleting auth key: %s", err)
+		}
+	})
+
+	ts := &tsnet.Server{
+		Hostname:  "test-proxy",
+		Ephemeral: true,
+		Dir:       t.TempDir(),
+		AuthKey:   authKey,
+	}
+	_, err = ts.Up(ctx)
+	if err != nil {
+		t.Fatal(err)
+	}
+	t.Cleanup(func() {
+		if err := ts.Close(); err != nil {
+			t.Errorf("error shutting down tsnet.Server: %s", err)
+		}
+	})
+
+	return ts
+}
+
+func hostNameFromOperatorSecret(t *testing.T, s corev1.Secret) string {
+	profiles := map[string]any{}
+	if err := json.Unmarshal(s.Data["_profiles"], &profiles); err != nil {
+		t.Fatal(err)
+	}
+	key, ok := strings.CutPrefix(string(s.Data["_current-profile"]), "profile-")
+	if !ok {
+		t.Fatal(string(s.Data["_current-profile"]))
+	}
+	profile, ok := profiles[key]
+	if !ok {
+		t.Fatal(profiles)
+	}
+
+	return ((profile.(map[string]any))["Name"]).(string)
+}

cmd/k8s-operator/egress-eps_test.go

@@ -112,7 +112,7 @@ func TestTailscaleEgressEndpointSlices(t *testing.T) {
 				Terminating: pointer.ToBool(false),
 			},
 		})
-		expectEqual(t, fc, eps, nil)
+		expectEqual(t, fc, eps)
 	})
 	t.Run("status_does_not_match_pod_ip", func(t *testing.T) {
 		_, stateS := podAndSecretForProxyGroup("foo")           // replica Pod has IP 10.0.0.1
@@ -122,7 +122,7 @@ func TestTailscaleEgressEndpointSlices(t *testing.T) {
 		})
 		expectReconciled(t, er, "operator-ns", "foo")
 		eps.Endpoints = []discoveryv1.Endpoint{}
-		expectEqual(t, fc, eps, nil)
+		expectEqual(t, fc, eps)
 	})
 }
 

cmd/k8s-operator/egress-services-readiness.go

@@ -64,7 +64,7 @@ func (esrr *egressSvcsReadinessReconciler) Reconcile(ctx context.Context, req re
 	oldStatus := svc.Status.DeepCopy()
 	defer func() {
 		tsoperator.SetServiceCondition(svc, tsapi.EgressSvcReady, st, reason, msg, esrr.clock, l)
-		if !apiequality.Semantic.DeepEqual(oldStatus, svc.Status) {
+		if !apiequality.Semantic.DeepEqual(oldStatus, &svc.Status) {
 			err = errors.Join(err, esrr.Status().Update(ctx, svc))
 		}
 	}()

cmd/k8s-operator/egress-services-readiness_test.go

@@ -67,24 +67,24 @@ func TestEgressServiceReadiness(t *testing.T) {
 	setClusterNotReady(egressSvc, cl, zl.Sugar())
 	t.Run("endpointslice_does_not_exist", func(t *testing.T) {
 		expectReconciled(t, rec, "dev", "my-app")
-		expectEqual(t, fc, egressSvc, nil) // not ready
+		expectEqual(t, fc, egressSvc) // not ready
 	})
 	t.Run("proxy_group_does_not_exist", func(t *testing.T) {
 		mustCreate(t, fc, eps)
 		expectReconciled(t, rec, "dev", "my-app")
-		expectEqual(t, fc, egressSvc, nil) // still not ready
+		expectEqual(t, fc, egressSvc) // still not ready
 	})
 	t.Run("proxy_group_not_ready", func(t *testing.T) {
 		mustCreate(t, fc, pg)
 		expectReconciled(t, rec, "dev", "my-app")
-		expectEqual(t, fc, egressSvc, nil) // still not ready
+		expectEqual(t, fc, egressSvc) // still not ready
 	})
 	t.Run("no_ready_replicas", func(t *testing.T) {
 		setPGReady(pg, cl, zl.Sugar())
 		mustUpdateStatus(t, fc, pg.Namespace, pg.Name, func(p *tsapi.ProxyGroup) {
 			p.Status = pg.Status
 		})
-		expectEqual(t, fc, pg, nil)
+		expectEqual(t, fc, pg)
 		for i := range pgReplicas(pg) {
 			p := pod(pg, i)
 			mustCreate(t, fc, p)
@@ -94,7 +94,7 @@ func TestEgressServiceReadiness(t *testing.T) {
 		}
 		expectReconciled(t, rec, "dev", "my-app")
 		setNotReady(egressSvc, cl, zl.Sugar(), pgReplicas(pg))
-		expectEqual(t, fc, egressSvc, nil) // still not ready
+		expectEqual(t, fc, egressSvc) // still not ready
 	})
 	t.Run("one_ready_replica", func(t *testing.T) {
 		setEndpointForReplica(pg, 0, eps)
@@ -103,7 +103,7 @@ func TestEgressServiceReadiness(t *testing.T) {
 		})
 		setReady(egressSvc, cl, zl.Sugar(), pgReplicas(pg), 1)
 		expectReconciled(t, rec, "dev", "my-app")
-		expectEqual(t, fc, egressSvc, nil) // partially ready
+		expectEqual(t, fc, egressSvc) // partially ready
 	})
 	t.Run("all_replicas_ready", func(t *testing.T) {
 		for i := range pgReplicas(pg) {
@@ -114,7 +114,7 @@ func TestEgressServiceReadiness(t *testing.T) {
 		})
 		setReady(egressSvc, cl, zl.Sugar(), pgReplicas(pg), pgReplicas(pg))
 		expectReconciled(t, rec, "dev", "my-app")
-		expectEqual(t, fc, egressSvc, nil) // ready
+		expectEqual(t, fc, egressSvc) // ready
 	})
 }
 

cmd/k8s-operator/egress-services.go

@@ -51,12 +51,12 @@ const (
 	labelSvcType = "tailscale.com/svc-type" // ingress or egress
 	typeEgress   = "egress"
 	// maxPorts is the maximum number of ports that can be exposed on a
-	// container. In practice this will be ports in range [3000 - 4000). The
+	// container. In practice this will be ports in range [10000 - 11000). The
 	// high range should make it easier to distinguish container ports from
 	// the tailnet target ports for debugging purposes (i.e when reading
-	// netfilter rules). The limit of 10000 is somewhat arbitrary, the
+	// netfilter rules). The limit of 1000 is somewhat arbitrary, the
 	// assumption is that this would not be hit in practice.
-	maxPorts = 10000
+	maxPorts = 1000
 
 	indexEgressProxyGroup = ".metadata.annotations.egress-proxy-group"
 )
@@ -123,7 +123,7 @@ func (esr *egressSvcsReconciler) Reconcile(ctx context.Context, req reconcile.Re
 
 	oldStatus := svc.Status.DeepCopy()
 	defer func() {
-		if !apiequality.Semantic.DeepEqual(oldStatus, svc.Status) {
+		if !apiequality.Semantic.DeepEqual(oldStatus, &svc.Status) {
 			err = errors.Join(err, esr.Status().Update(ctx, svc))
 		}
 	}()
@@ -136,9 +136,8 @@ func (esr *egressSvcsReconciler) Reconcile(ctx context.Context, req reconcile.Re
 	}
 
 	if !slices.Contains(svc.Finalizers, FinalizerName) {
-		l.Infof("configuring tailnet service") // logged exactly once
 		svc.Finalizers = append(svc.Finalizers, FinalizerName)
-		if err := esr.Update(ctx, svc); err != nil {
+		if err := esr.updateSvcSpec(ctx, svc); err != nil {
 			err := fmt.Errorf("failed to add finalizer: %w", err)
 			r := svcConfiguredReason(svc, false, l)
 			tsoperator.SetServiceCondition(svc, tsapi.EgressSvcConfigured, metav1.ConditionFalse, r, err.Error(), esr.clock, l)
@@ -157,7 +156,15 @@ func (esr *egressSvcsReconciler) Reconcile(ctx context.Context, req reconcile.Re
 		return res, err
 	}
 
-	return res, esr.maybeProvision(ctx, svc, l)
+	if err := esr.maybeProvision(ctx, svc, l); err != nil {
+		if strings.Contains(err.Error(), optimisticLockErrorMsg) {
+			l.Infof("optimistic lock error, retrying: %s", err)
+		} else {
+			return reconcile.Result{}, err
+		}
+	}
+
+	return res, nil
 }
 
 func (esr *egressSvcsReconciler) maybeProvision(ctx context.Context, svc *corev1.Service, l *zap.SugaredLogger) (err error) {
@@ -198,7 +205,7 @@ func (esr *egressSvcsReconciler) maybeProvision(ctx context.Context, svc *corev1
 	if svc.Spec.ExternalName != clusterIPSvcFQDN {
 		l.Infof("Configuring ExternalName Service to point to ClusterIP Service %s", clusterIPSvcFQDN)
 		svc.Spec.ExternalName = clusterIPSvcFQDN
-		if err = esr.Update(ctx, svc); err != nil {
+		if err = esr.updateSvcSpec(ctx, svc); err != nil {
 			err = fmt.Errorf("error updating ExternalName Service: %w", err)
 			return err
 		}
@@ -222,6 +229,15 @@ func (esr *egressSvcsReconciler) provision(ctx context.Context, proxyGroupName s
 		found := false
 		for _, wantsPM := range svc.Spec.Ports {
 			if wantsPM.Port == pm.Port && strings.EqualFold(string(wantsPM.Protocol), string(pm.Protocol)) {
+				// We don't use the port name to distinguish this port internally, but Kubernetes
+				// require that, for Service ports with more than one name each port is uniquely named.
+				// So we can always pick the port name from the ExternalName Service as at this point we
+				// know that those are valid names because Kuberentes already validated it once. Note
+				// that users could have changed an unnamed port to a named port and might have changed
+				// port names- this should still work.
+				// https://kubernetes.io/docs/concepts/services-networking/service/#multi-port-services
+				// See also https://github.com/tailscale/tailscale/issues/13406#issuecomment-2507230388
+				clusterIPSvc.Spec.Ports[i].Name = wantsPM.Name
 				found = true
 				break
 			}
@@ -246,7 +262,7 @@ func (esr *egressSvcsReconciler) provision(ctx context.Context, proxyGroupName s
 		if !found {
 			// Calculate a free port to expose on container and add
 			// a new PortMap to the ClusterIP Service.
-			if usedPorts.Len() == maxPorts {
+			if usedPorts.Len() >= maxPorts {
 				// TODO(irbekrm): refactor to avoid extra reconciles here. Low priority as in practice,
 				// the limit should not be hit.
 				return nil, false, fmt.Errorf("unable to allocate additional ports on ProxyGroup %s, %d ports already used. Create another ProxyGroup or open an issue if you believe this is unexpected.", proxyGroupName, maxPorts)
@@ -479,13 +495,6 @@ func (esr *egressSvcsReconciler) validateClusterResources(ctx context.Context, s
 		tsoperator.RemoveServiceCondition(svc, tsapi.EgressSvcConfigured)
 		return false, err
 	}
-	if !tsoperator.ProxyGroupIsReady(pg) {
-		l.Infof("ProxyGroup %s is not ready, waiting...", proxyGroupName)
-		tsoperator.SetServiceCondition(svc, tsapi.EgressSvcValid, metav1.ConditionUnknown, reasonProxyGroupNotReady, reasonProxyGroupNotReady, esr.clock, l)
-		tsoperator.RemoveServiceCondition(svc, tsapi.EgressSvcConfigured)
-		return false, nil
-	}
-
 	if violations := validateEgressService(svc, pg); len(violations) > 0 {
 		msg := fmt.Sprintf("invalid egress Service: %s", strings.Join(violations, ", "))
 		esr.recorder.Event(svc, corev1.EventTypeWarning, "INVALIDSERVICE", msg)
@@ -494,6 +503,13 @@ func (esr *egressSvcsReconciler) validateClusterResources(ctx context.Context, s
 		tsoperator.RemoveServiceCondition(svc, tsapi.EgressSvcConfigured)
 		return false, nil
 	}
+	if !tsoperator.ProxyGroupIsReady(pg) {
+		l.Infof("ProxyGroup %s is not ready, waiting...", proxyGroupName)
+		tsoperator.SetServiceCondition(svc, tsapi.EgressSvcValid, metav1.ConditionUnknown, reasonProxyGroupNotReady, reasonProxyGroupNotReady, esr.clock, l)
+		tsoperator.RemoveServiceCondition(svc, tsapi.EgressSvcConfigured)
+		return false, nil
+	}
+
 	l.Debugf("egress service is valid")
 	tsoperator.SetServiceCondition(svc, tsapi.EgressSvcValid, metav1.ConditionTrue, reasonEgressSvcValid, reasonEgressSvcValid, esr.clock, l)
 	return true, nil
@@ -540,13 +556,13 @@ func svcNameBase(s string) string {
 	}
 }
 
-// unusedPort returns a port in range [3000 - 4000). The caller must ensure that
-// usedPorts does not contain all ports in range [3000 - 4000).
+// unusedPort returns a port in range [10000 - 11000). The caller must ensure that
+// usedPorts does not contain all ports in range [10000 - 11000).
 func unusedPort(usedPorts sets.Set[int32]) int32 {
 	foundFreePort := false
 	var suggestPort int32
 	for !foundFreePort {
-		suggestPort = rand.Int32N(maxPorts) + 3000
+		suggestPort = rand.Int32N(maxPorts) + 10000
 		if !usedPorts.Has(suggestPort) {
 			foundFreePort = true
 		}
@@ -714,3 +730,13 @@ func epsPortsFromSvc(svc *corev1.Service) (ep []discoveryv1.EndpointPort) {
 	}
 	return ep
 }
+
+// updateSvcSpec ensures that the given Service's spec is updated in cluster, but the local Service object still retains
+// the not-yet-applied status.
+// TODO(irbekrm): once we do SSA for these patch updates, this will no longer be needed.
+func (esr *egressSvcsReconciler) updateSvcSpec(ctx context.Context, svc *corev1.Service) error {
+	st := svc.Status.DeepCopy()
+	err := esr.Update(ctx, svc)
+	svc.Status = *st
+	return err
+}

cmd/k8s-operator/egress-services_test.go

@@ -96,7 +96,7 @@ func TestTailscaleEgressServices(t *testing.T) {
 		expectReconciled(t, esr, "default", "test")
 		// Service should have EgressSvcValid condition set to Unknown.
 		svc.Status.Conditions = []metav1.Condition{condition(tsapi.EgressSvcValid, metav1.ConditionUnknown, reasonProxyGroupNotReady, reasonProxyGroupNotReady, clock)}
-		expectEqual(t, fc, svc, nil)
+		expectEqual(t, fc, svc)
 	})
 
 	t.Run("proxy_group_ready", func(t *testing.T) {
@@ -105,28 +105,40 @@ func TestTailscaleEgressServices(t *testing.T) {
 				condition(tsapi.ProxyGroupReady, metav1.ConditionTrue, "", "", clock),
 			}
 		})
-		// Quirks of the fake client.
-		mustUpdateStatus(t, fc, "default", "test", func(svc *corev1.Service) {
-			svc.Status.Conditions = []metav1.Condition{}
+		expectReconciled(t, esr, "default", "test")
+		validateReadyService(t, fc, esr, svc, clock, zl, cm)
+	})
+	t.Run("service_retain_one_unnamed_port", func(t *testing.T) {
+		svc.Spec.Ports = []corev1.ServicePort{{Protocol: "TCP", Port: 80}}
+		mustUpdate(t, fc, "default", "test", func(s *corev1.Service) {
+			s.Spec.Ports = svc.Spec.Ports
 		})
 		expectReconciled(t, esr, "default", "test")
-		// Verify that a ClusterIP Service has been created.
-		name := findGenNameForEgressSvcResources(t, fc, svc)
-		expectEqual(t, fc, clusterIPSvc(name, svc), removeTargetPortsFromSvc)
-		clusterSvc := mustGetClusterIPSvc(t, fc, name)
-		// Verify that an EndpointSlice has been created.
-		expectEqual(t, fc, endpointSlice(name, svc, clusterSvc), nil)
-		// Verify that ConfigMap contains configuration for the new egress service.
-		mustHaveConfigForSvc(t, fc, svc, clusterSvc, cm)
-		r := svcConfiguredReason(svc, true, zl.Sugar())
-		// Verify that the user-created ExternalName Service has Configured set to true and ExternalName pointing to the
-		// CluterIP Service.
-		svc.Status.Conditions = []metav1.Condition{
-			condition(tsapi.EgressSvcConfigured, metav1.ConditionTrue, r, r, clock),
-		}
-		svc.ObjectMeta.Finalizers = []string{"tailscale.com/finalizer"}
-		svc.Spec.ExternalName = fmt.Sprintf("%s.operator-ns.svc.cluster.local", name)
-		expectEqual(t, fc, svc, nil)
+		validateReadyService(t, fc, esr, svc, clock, zl, cm)
+	})
+	t.Run("service_add_two_named_ports", func(t *testing.T) {
+		svc.Spec.Ports = []corev1.ServicePort{{Protocol: "TCP", Port: 80, Name: "http"}, {Protocol: "TCP", Port: 443, Name: "https"}}
+		mustUpdate(t, fc, "default", "test", func(s *corev1.Service) {
+			s.Spec.Ports = svc.Spec.Ports
+		})
+		expectReconciled(t, esr, "default", "test")
+		validateReadyService(t, fc, esr, svc, clock, zl, cm)
+	})
+	t.Run("service_add_udp_port", func(t *testing.T) {
+		svc.Spec.Ports = append(svc.Spec.Ports, corev1.ServicePort{Port: 53, Protocol: "UDP", Name: "dns"})
+		mustUpdate(t, fc, "default", "test", func(s *corev1.Service) {
+			s.Spec.Ports = svc.Spec.Ports
+		})
+		expectReconciled(t, esr, "default", "test")
+		validateReadyService(t, fc, esr, svc, clock, zl, cm)
+	})
+	t.Run("service_change_protocol", func(t *testing.T) {
+		svc.Spec.Ports = []corev1.ServicePort{{Protocol: "TCP", Port: 80, Name: "http"}, {Protocol: "TCP", Port: 443, Name: "https"}, {Port: 53, Protocol: "TCP", Name: "tcp_dns"}}
+		mustUpdate(t, fc, "default", "test", func(s *corev1.Service) {
+			s.Spec.Ports = svc.Spec.Ports
+		})
+		expectReconciled(t, esr, "default", "test")
+		validateReadyService(t, fc, esr, svc, clock, zl, cm)
 	})
 
 	t.Run("delete_external_name_service", func(t *testing.T) {
@@ -143,6 +155,29 @@ func TestTailscaleEgressServices(t *testing.T) {
 	})
 }
 
+func validateReadyService(t *testing.T, fc client.WithWatch, esr *egressSvcsReconciler, svc *corev1.Service, clock *tstest.Clock, zl *zap.Logger, cm *corev1.ConfigMap) {
+	expectReconciled(t, esr, "default", "test")
+	// Verify that a ClusterIP Service has been created.
+	name := findGenNameForEgressSvcResources(t, fc, svc)
+	expectEqual(t, fc, clusterIPSvc(name, svc), removeTargetPortsFromSvc)
+	clusterSvc := mustGetClusterIPSvc(t, fc, name)
+	// Verify that an EndpointSlice has been created.
+	expectEqual(t, fc, endpointSlice(name, svc, clusterSvc))
+	// Verify that ConfigMap contains configuration for the new egress service.
+	mustHaveConfigForSvc(t, fc, svc, clusterSvc, cm)
+	r := svcConfiguredReason(svc, true, zl.Sugar())
+	// Verify that the user-created ExternalName Service has Configured set to true and ExternalName pointing to the
+	// CluterIP Service.
+	svc.Status.Conditions = []metav1.Condition{
+		condition(tsapi.EgressSvcValid, metav1.ConditionTrue, "EgressSvcValid", "EgressSvcValid", clock),
+		condition(tsapi.EgressSvcConfigured, metav1.ConditionTrue, r, r, clock),
+	}
+	svc.ObjectMeta.Finalizers = []string{"tailscale.com/finalizer"}
+	svc.Spec.ExternalName = fmt.Sprintf("%s.operator-ns.svc.cluster.local", name)
+	expectEqual(t, fc, svc)
+
+}
+
 func condition(typ tsapi.ConditionType, st metav1.ConditionStatus, r, msg string, clock tstime.Clock) metav1.Condition {
 	return metav1.Condition{
 		Type:               string(typ),

cmd/k8s-operator/ingress-for-pg.go

@@ -0,0 +1,569 @@
+// Copyright (c) Tailscale Inc & AUTHORS
+// SPDX-License-Identifier: BSD-3-Clause
+
+//go:build !plan9
+
+package main
+
+import (
+	"context"
+	"encoding/json"
+	"errors"
+	"fmt"
+	"net/http"
+	"reflect"
+	"slices"
+	"strings"
+	"sync"
+
+	"go.uber.org/zap"
+	corev1 "k8s.io/api/core/v1"
+	networkingv1 "k8s.io/api/networking/v1"
+	apiequality "k8s.io/apimachinery/pkg/api/equality"
+	apierrors "k8s.io/apimachinery/pkg/api/errors"
+	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
+	"k8s.io/apimachinery/pkg/types"
+	"k8s.io/client-go/tools/record"
+	"sigs.k8s.io/controller-runtime/pkg/client"
+	"sigs.k8s.io/controller-runtime/pkg/reconcile"
+	"tailscale.com/client/tailscale"
+	"tailscale.com/ipn"
+	"tailscale.com/ipn/ipnstate"
+	tsoperator "tailscale.com/k8s-operator"
+	tsapi "tailscale.com/k8s-operator/apis/v1alpha1"
+	"tailscale.com/kube/kubetypes"
+	"tailscale.com/tailcfg"
+	"tailscale.com/util/clientmetric"
+	"tailscale.com/util/dnsname"
+	"tailscale.com/util/mak"
+	"tailscale.com/util/set"
+)
+
+const (
+	serveConfigKey = "serve-config.json"
+	VIPSvcOwnerRef = "tailscale.com/k8s-operator:owned-by:%s"
+	// FinalizerNamePG is the finalizer used by the IngressPGReconciler
+	FinalizerNamePG = "tailscale.com/ingress-pg-finalizer"
+)
+
+var gaugePGIngressResources = clientmetric.NewGauge(kubetypes.MetricIngressPGResourceCount)
+
+// IngressPGReconciler is a controller that reconciles Tailscale Ingresses should be exposed on an ingress ProxyGroup
+// (in HA mode).
+type IngressPGReconciler struct {
+	client.Client
+
+	recorder    record.EventRecorder
+	logger      *zap.SugaredLogger
+	tsClient    tsClient
+	tsnetServer tsnetServer
+	tsNamespace string
+	lc          localClient
+	defaultTags []string
+
+	mu sync.Mutex // protects following
+	// managedIngresses is a set of all ingress resources that we're currently
+	// managing. This is only used for metrics.
+	managedIngresses set.Slice[types.UID]
+}
+
+// Reconcile reconciles Ingresses that should be exposed over Tailscale in HA mode (on a ProxyGroup). It looks at all
+// Ingresses with tailscale.com/proxy-group annotation. For each such Ingress, it ensures that a VIPService named after
+// the hostname of the Ingress exists and is up to date. It also ensures that the serve config for the ingress
+// ProxyGroup is updated to route traffic for the VIPService to the Ingress's backend Services.
+// When an Ingress is deleted or unexposed, the VIPService and the associated serve config are cleaned up.
+// Ingress hostname change also results in the VIPService for the previous hostname being cleaned up and a new VIPService
+// being created for the new hostname.
+func (a *IngressPGReconciler) Reconcile(ctx context.Context, req reconcile.Request) (res reconcile.Result, err error) {
+	logger := a.logger.With("Ingress", req.NamespacedName)
+	logger.Debugf("starting reconcile")
+	defer logger.Debugf("reconcile finished")
+
+	ing := new(networkingv1.Ingress)
+	err = a.Get(ctx, req.NamespacedName, ing)
+	if apierrors.IsNotFound(err) {
+		// Request object not found, could have been deleted after reconcile request.
+		logger.Debugf("Ingress not found, assuming it was deleted")
+		return res, nil
+	} else if err != nil {
+		return res, fmt.Errorf("failed to get Ingress: %w", err)
+	}
+
+	// hostname is the name of the VIPService that will be created for this Ingress as well as the first label in
+	// the MagicDNS name of the Ingress.
+	hostname := hostnameForIngress(ing)
+	logger = logger.With("hostname", hostname)
+
+	if !ing.DeletionTimestamp.IsZero() || !a.shouldExpose(ing) {
+		return res, a.maybeCleanup(ctx, hostname, ing, logger)
+	}
+
+	if err := a.maybeProvision(ctx, hostname, ing, logger); err != nil {
+		return res, fmt.Errorf("failed to provision: %w", err)
+	}
+	return res, nil
+}
+
+// maybeProvision ensures that the VIPService and serve config for the Ingress are created or updated.
+func (a *IngressPGReconciler) maybeProvision(ctx context.Context, hostname string, ing *networkingv1.Ingress, logger *zap.SugaredLogger) error {
+	if err := validateIngressClass(ctx, a.Client); err != nil {
+		logger.Infof("error validating tailscale IngressClass: %v.", err)
+		return nil
+	}
+
+	// Get and validate ProxyGroup readiness
+	pgName := ing.Annotations[AnnotationProxyGroup]
+	if pgName == "" {
+		logger.Infof("[unexpected] no ProxyGroup annotation, skipping VIPService provisioning")
+		return nil
+	}
+	pg := &tsapi.ProxyGroup{}
+	if err := a.Get(ctx, client.ObjectKey{Name: pgName}, pg); err != nil {
+		if apierrors.IsNotFound(err) {
+			logger.Infof("ProxyGroup %q does not exist", pgName)
+			return nil
+		}
+		return fmt.Errorf("getting ProxyGroup %q: %w", pgName, err)
+	}
+	if !tsoperator.ProxyGroupIsReady(pg) {
+		// TODO(irbekrm): we need to reconcile ProxyGroup Ingresses on ProxyGroup changes to not miss the status update
+		// in this case.
+		logger.Infof("ProxyGroup %q is not ready", pgName)
+		return nil
+	}
+
+	// Validate Ingress configuration
+	if err := a.validateIngress(ing, pg); err != nil {
+		logger.Infof("invalid Ingress configuration: %v", err)
+		a.recorder.Event(ing, corev1.EventTypeWarning, "InvalidIngressConfiguration", err.Error())
+		return nil
+	}
+
+	if !IsHTTPSEnabledOnTailnet(a.tsnetServer) {
+		a.recorder.Event(ing, corev1.EventTypeWarning, "HTTPSNotEnabled", "HTTPS is not enabled on the tailnet; ingress may not work")
+	}
+
+	logger = logger.With("proxy-group", pg)
+
+	if !slices.Contains(ing.Finalizers, FinalizerNamePG) {
+		// This log line is printed exactly once during initial provisioning,
+		// because once the finalizer is in place this block gets skipped. So,
+		// this is a nice place to tell the operator that the high level,
+		// multi-reconcile operation is underway.
+		logger.Infof("exposing Ingress over tailscale")
+		ing.Finalizers = append(ing.Finalizers, FinalizerNamePG)
+		if err := a.Update(ctx, ing); err != nil {
+			return fmt.Errorf("failed to add finalizer: %w", err)
+		}
+		a.mu.Lock()
+		a.managedIngresses.Add(ing.UID)
+		gaugePGIngressResources.Set(int64(a.managedIngresses.Len()))
+		a.mu.Unlock()
+	}
+
+	// 1. Ensure that if Ingress' hostname has changed, any VIPService resources corresponding to the old hostname
+	// are cleaned up.
+	// In practice, this function will ensure that any VIPServices that are associated with the provided ProxyGroup
+	// and no longer owned by an Ingress are cleaned up. This is fine- it is not expensive and ensures that in edge
+	// cases (a single update changed both hostname and removed ProxyGroup annotation) the VIPService is more likely
+	// to be (eventually) removed.
+	if err := a.maybeCleanupProxyGroup(ctx, pgName, logger); err != nil {
+		return fmt.Errorf("failed to cleanup VIPService resources for ProxyGroup: %w", err)
+	}
+
+	// 2. Ensure that there isn't a VIPService with the same hostname already created and not owned by this Ingress.
+	// TODO(irbekrm): perhaps in future we could have record names being stored on VIPServices. I am not certain if
+	// there might not be edge cases (custom domains, etc?) where attempting to determine the DNS name of the
+	// VIPService in this way won't be incorrect.
+	tcd, err := a.tailnetCertDomain(ctx)
+	if err != nil {
+		return fmt.Errorf("error determining DNS name base: %w", err)
+	}
+	dnsName := hostname + "." + tcd
+	existingVIPSvc, err := a.tsClient.getVIPServiceByName(ctx, hostname)
+	// TODO(irbekrm): here and when creating the VIPService, verify if the error is not terminal (and therefore
+	// should not be reconciled). For example, if the hostname is already a hostname of a Tailscale node, the GET
+	// here will fail.
+	if err != nil {
+		errResp := &tailscale.ErrResponse{}
+		if ok := errors.As(err, errResp); ok && errResp.Status != http.StatusNotFound {
+			return fmt.Errorf("error getting VIPService %q: %w", hostname, err)
+		}
+	}
+	if existingVIPSvc != nil && !isVIPServiceForIngress(existingVIPSvc, ing) {
+		logger.Infof("VIPService %q for MagicDNS name %q  already exists, but is not owned by this Ingress. Please delete it manually and recreate this Ingress to proceed or create an Ingress for a different MagicDNS name", hostname, dnsName)
+		a.recorder.Event(ing, corev1.EventTypeWarning, "ConflictingVIPServiceExists", fmt.Sprintf("VIPService %q for MagicDNS name %q already exists, but is not owned by this Ingress. Please delete it manually to proceed or create an Ingress for a different MagicDNS name", hostname, dnsName))
+		return nil
+	}
+
+	// 3. Ensure that the serve config for the ProxyGroup contains the VIPService
+	cm, cfg, err := a.proxyGroupServeConfig(ctx, pgName)
+	if err != nil {
+		return fmt.Errorf("error getting ingress serve config: %w", err)
+	}
+	if cm == nil {
+		logger.Infof("no ingress serve config ConfigMap found, unable to update serve config. Ensure that ProxyGroup is healthy.")
+		return nil
+	}
+	ep := ipn.HostPort(fmt.Sprintf("%s:443", dnsName))
+	handlers, err := handlersForIngress(ctx, ing, a.Client, a.recorder, dnsName, logger)
+	if err != nil {
+		return fmt.Errorf("failed to get handlers for ingress: %w", err)
+	}
+	ingCfg := &ipn.ServiceConfig{
+		TCP: map[uint16]*ipn.TCPPortHandler{
+			443: {
+				HTTPS: true,
+			},
+		},
+		Web: map[ipn.HostPort]*ipn.WebServerConfig{
+			ep: {
+				Handlers: handlers,
+			},
+		},
+	}
+	serviceName := tailcfg.ServiceName("svc:" + hostname)
+	var gotCfg *ipn.ServiceConfig
+	if cfg != nil && cfg.Services != nil {
+		gotCfg = cfg.Services[serviceName]
+	}
+	if !reflect.DeepEqual(gotCfg, ingCfg) {
+		logger.Infof("Updating serve config")
+		mak.Set(&cfg.Services, serviceName, ingCfg)
+		cfgBytes, err := json.Marshal(cfg)
+		if err != nil {
+			return fmt.Errorf("error marshaling serve config: %w", err)
+		}
+		mak.Set(&cm.BinaryData, serveConfigKey, cfgBytes)
+		if err := a.Update(ctx, cm); err != nil {
+			return fmt.Errorf("error updating serve config: %w", err)
+		}
+	}
+
+	// 4. Ensure that the VIPService exists and is up to date.
+	tags := a.defaultTags
+	if tstr, ok := ing.Annotations[AnnotationTags]; ok {
+		tags = strings.Split(tstr, ",")
+	}
+
+	vipSvc := &VIPService{
+		Name:    hostname,
+		Tags:    tags,
+		Ports:   []string{"443"}, // always 443 for Ingress
+		Comment: fmt.Sprintf(VIPSvcOwnerRef, ing.UID),
+	}
+	if existingVIPSvc != nil {
+		vipSvc.Addrs = existingVIPSvc.Addrs
+	}
+	if existingVIPSvc == nil || !reflect.DeepEqual(vipSvc.Tags, existingVIPSvc.Tags) {
+		logger.Infof("Ensuring VIPService %q exists and is up to date", hostname)
+		if err := a.tsClient.createOrUpdateVIPServiceByName(ctx, vipSvc); err != nil {
+			logger.Infof("error creating VIPService: %v", err)
+			return fmt.Errorf("error creating VIPService: %w", err)
+		}
+	}
+
+	// 5. Update Ingress status
+	oldStatus := ing.Status.DeepCopy()
+	// TODO(irbekrm): once we have ingress ProxyGroup, we can determine if instances are ready to route traffic to the VIPService
+	ing.Status.LoadBalancer.Ingress = []networkingv1.IngressLoadBalancerIngress{
+		{
+			Hostname: dnsName,
+			Ports: []networkingv1.IngressPortStatus{
+				{
+					Protocol: "TCP",
+					Port:     443,
+				},
+			},
+		},
+	}
+	if apiequality.Semantic.DeepEqual(oldStatus, ing.Status) {
+		return nil
+	}
+	if err := a.Status().Update(ctx, ing); err != nil {
+		return fmt.Errorf("failed to update Ingress status: %w", err)
+	}
+	return nil
+}
+
+// maybeCleanupProxyGroup ensures that if an Ingress hostname has changed, any VIPService resources created for the
+// Ingress' ProxyGroup corresponding to the old hostname are cleaned up. A run of this function will ensure that any
+// VIPServices that are associated with the provided ProxyGroup and no longer owned by an Ingress are cleaned up.
+func (a *IngressPGReconciler) maybeCleanupProxyGroup(ctx context.Context, proxyGroupName string, logger *zap.SugaredLogger) error {
+	// Get serve config for the ProxyGroup
+	cm, cfg, err := a.proxyGroupServeConfig(ctx, proxyGroupName)
+	if err != nil {
+		return fmt.Errorf("getting serve config: %w", err)
+	}
+	if cfg == nil {
+		return nil // ProxyGroup does not have any VIPServices
+	}
+
+	ingList := &networkingv1.IngressList{}
+	if err := a.List(ctx, ingList); err != nil {
+		return fmt.Errorf("listing Ingresses: %w", err)
+	}
+	serveConfigChanged := false
+	// For each VIPService in serve config...
+	for vipHostname := range cfg.Services {
+		// ...check if there is currently an Ingress with this hostname
+		found := false
+		for _, i := range ingList.Items {
+			ingressHostname := hostnameForIngress(&i)
+			if ingressHostname == vipHostname.WithoutPrefix() {
+				found = true
+				break
+			}
+		}
+
+		if !found {
+			logger.Infof("VIPService %q is not owned by any Ingress, cleaning up", vipHostname)
+			svc, err := a.getVIPService(ctx, vipHostname.WithoutPrefix(), logger)
+			if err != nil {
+				errResp := &tailscale.ErrResponse{}
+				if errors.As(err, &errResp) && errResp.Status == http.StatusNotFound {
+					delete(cfg.Services, vipHostname)
+					serveConfigChanged = true
+					continue
+				}
+				return err
+			}
+			if isVIPServiceForAnyIngress(svc) {
+				logger.Infof("cleaning up orphaned VIPService %q", vipHostname)
+				if err := a.tsClient.deleteVIPServiceByName(ctx, vipHostname.WithoutPrefix()); err != nil {
+					errResp := &tailscale.ErrResponse{}
+					if !errors.As(err, &errResp) || errResp.Status != http.StatusNotFound {
+						return fmt.Errorf("deleting VIPService %q: %w", vipHostname, err)
+					}
+				}
+			}
+			delete(cfg.Services, vipHostname)
+			serveConfigChanged = true
+		}
+	}
+
+	if serveConfigChanged {
+		cfgBytes, err := json.Marshal(cfg)
+		if err != nil {
+			return fmt.Errorf("marshaling serve config: %w", err)
+		}
+		mak.Set(&cm.BinaryData, serveConfigKey, cfgBytes)
+		if err := a.Update(ctx, cm); err != nil {
+			return fmt.Errorf("updating serve config: %w", err)
+		}
+	}
+	return nil
+}
+
+// maybeCleanup ensures that any resources, such as a VIPService created for this Ingress, are cleaned up when the
+// Ingress is being deleted or is unexposed.
+func (a *IngressPGReconciler) maybeCleanup(ctx context.Context, hostname string, ing *networkingv1.Ingress, logger *zap.SugaredLogger) error {
+	logger.Debugf("Ensuring any resources for Ingress are cleaned up")
+	ix := slices.Index(ing.Finalizers, FinalizerNamePG)
+	if ix < 0 {
+		logger.Debugf("no finalizer, nothing to do")
+		a.mu.Lock()
+		defer a.mu.Unlock()
+		a.managedIngresses.Remove(ing.UID)
+		gaugePGIngressResources.Set(int64(a.managedIngresses.Len()))
+		return nil
+	}
+
+	// 1. Check if there is a VIPService created for this Ingress.
+	pg := ing.Annotations[AnnotationProxyGroup]
+	cm, cfg, err := a.proxyGroupServeConfig(ctx, pg)
+	if err != nil {
+		return fmt.Errorf("error getting ProxyGroup serve config: %w", err)
+	}
+	serviceName := tailcfg.ServiceName("svc:" + hostname)
+	// VIPService is always first added to serve config and only then created in the Tailscale API, so if it is not
+	// found in the serve config, we can assume that there is no VIPService. TODO(irbekrm): once we have ingress
+	// ProxyGroup, we will probably add currently exposed VIPServices to its status. At that point, we can use the
+	// status rather than checking the serve config each time.
+	if cfg == nil || cfg.Services == nil || cfg.Services[serviceName] == nil {
+		return nil
+	}
+	logger.Infof("Ensuring that VIPService %q configuration is cleaned up", hostname)
+
+	// 2. Delete the VIPService.
+	if err := a.deleteVIPServiceIfExists(ctx, hostname, ing, logger); err != nil {
+		return fmt.Errorf("error deleting VIPService: %w", err)
+	}
+
+	// 3. Remove the VIPService from the serve config for the ProxyGroup.
+	logger.Infof("Removing VIPService %q from serve config for ProxyGroup %q", hostname, pg)
+	delete(cfg.Services, serviceName)
+	cfgBytes, err := json.Marshal(cfg)
+	if err != nil {
+		return fmt.Errorf("error marshaling serve config: %w", err)
+	}
+	mak.Set(&cm.BinaryData, serveConfigKey, cfgBytes)
+	if err := a.Update(ctx, cm); err != nil {
+		return fmt.Errorf("error updating ConfigMap %q: %w", cm.Name, err)
+	}
+
+	if err := a.deleteFinalizer(ctx, ing, logger); err != nil {
+		return fmt.Errorf("failed to remove finalizer: %w", err)
+	}
+	a.mu.Lock()
+	defer a.mu.Unlock()
+	a.managedIngresses.Remove(ing.UID)
+	gaugePGIngressResources.Set(int64(a.managedIngresses.Len()))
+	return nil
+}
+
+func (a *IngressPGReconciler) deleteFinalizer(ctx context.Context, ing *networkingv1.Ingress, logger *zap.SugaredLogger) error {
+	found := false
+	ing.Finalizers = slices.DeleteFunc(ing.Finalizers, func(f string) bool {
+		found = true
+		return f == FinalizerNamePG
+	})
+	if !found {
+		return nil
+	}
+	logger.Debug("ensure %q finalizer is removed", FinalizerNamePG)
+
+	if err := a.Update(ctx, ing); err != nil {
+		return fmt.Errorf("failed to remove finalizer %q: %w", FinalizerNamePG, err)
+	}
+	return nil
+}
+
+func pgIngressCMName(pg string) string {
+	return fmt.Sprintf("%s-ingress-config", pg)
+}
+
+func (a *IngressPGReconciler) proxyGroupServeConfig(ctx context.Context, pg string) (cm *corev1.ConfigMap, cfg *ipn.ServeConfig, err error) {
+	name := pgIngressCMName(pg)
+	cm = &corev1.ConfigMap{
+		ObjectMeta: metav1.ObjectMeta{
+			Name:      name,
+			Namespace: a.tsNamespace,
+		},
+	}
+	if err := a.Get(ctx, client.ObjectKeyFromObject(cm), cm); err != nil && !apierrors.IsNotFound(err) {
+		return nil, nil, fmt.Errorf("error retrieving ingress serve config ConfigMap %s: %v", name, err)
+	}
+	if apierrors.IsNotFound(err) {
+		return nil, nil, nil
+	}
+	cfg = &ipn.ServeConfig{}
+	if len(cm.BinaryData[serveConfigKey]) != 0 {
+		if err := json.Unmarshal(cm.BinaryData[serveConfigKey], cfg); err != nil {
+			return nil, nil, fmt.Errorf("error unmarshaling ingress serve config %v: %w", cm.BinaryData[serveConfigKey], err)
+		}
+	}
+	return cm, cfg, nil
+}
+
+type localClient interface {
+	StatusWithoutPeers(ctx context.Context) (*ipnstate.Status, error)
+}
+
+// tailnetCertDomain returns the base domain (TCD) of the current tailnet.
+func (a *IngressPGReconciler) tailnetCertDomain(ctx context.Context) (string, error) {
+	st, err := a.lc.StatusWithoutPeers(ctx)
+	if err != nil {
+		return "", fmt.Errorf("error getting tailscale status: %w", err)
+	}
+	return st.CurrentTailnet.MagicDNSSuffix, nil
+}
+
+// shouldExpose returns true if the Ingress should be exposed over Tailscale in HA mode (on a ProxyGroup)
+func (a *IngressPGReconciler) shouldExpose(ing *networkingv1.Ingress) bool {
+	isTSIngress := ing != nil &&
+		ing.Spec.IngressClassName != nil &&
+		*ing.Spec.IngressClassName == tailscaleIngressClassName
+	pgAnnot := ing.Annotations[AnnotationProxyGroup]
+	return isTSIngress && pgAnnot != ""
+}
+
+func (a *IngressPGReconciler) getVIPService(ctx context.Context, hostname string, logger *zap.SugaredLogger) (*VIPService, error) {
+	svc, err := a.tsClient.getVIPServiceByName(ctx, hostname)
+	if err != nil {
+		errResp := &tailscale.ErrResponse{}
+		if ok := errors.As(err, errResp); ok && errResp.Status != http.StatusNotFound {
+			logger.Infof("error getting VIPService %q: %v", hostname, err)
+			return nil, fmt.Errorf("error getting VIPService %q: %w", hostname, err)
+		}
+	}
+	return svc, nil
+}
+
+func isVIPServiceForIngress(svc *VIPService, ing *networkingv1.Ingress) bool {
+	if svc == nil || ing == nil {
+		return false
+	}
+	return strings.EqualFold(svc.Comment, fmt.Sprintf(VIPSvcOwnerRef, ing.UID))
+}
+
+func isVIPServiceForAnyIngress(svc *VIPService) bool {
+	if svc == nil {
+		return false
+	}
+	return strings.HasPrefix(svc.Comment, "tailscale.com/k8s-operator:owned-by:")
+}
+
+// validateIngress validates that the Ingress is properly configured.
+// Currently validates:
+// - Any tags provided via tailscale.com/tags annotation are valid Tailscale ACL tags
+// - The derived hostname is a valid DNS label
+// - The referenced ProxyGroup exists and is of type 'ingress'
+// - Ingress' TLS block is invalid
+func (a *IngressPGReconciler) validateIngress(ing *networkingv1.Ingress, pg *tsapi.ProxyGroup) error {
+	var errs []error
+
+	// Validate tags if present
+	if tstr, ok := ing.Annotations[AnnotationTags]; ok {
+		tags := strings.Split(tstr, ",")
+		for _, tag := range tags {
+			tag = strings.TrimSpace(tag)
+			if err := tailcfg.CheckTag(tag); err != nil {
+				errs = append(errs, fmt.Errorf("tailscale.com/tags annotation contains invalid tag %q: %w", tag, err))
+			}
+		}
+	}
+
+	// Validate TLS configuration
+	if ing.Spec.TLS != nil && len(ing.Spec.TLS) > 0 && (len(ing.Spec.TLS) > 1 || len(ing.Spec.TLS[0].Hosts) > 1) {
+		errs = append(errs, fmt.Errorf("Ingress contains invalid TLS block %v: only a single TLS entry with a single host is allowed", ing.Spec.TLS))
+	}
+
+	// Validate that the hostname will be a valid DNS label
+	hostname := hostnameForIngress(ing)
+	if err := dnsname.ValidLabel(hostname); err != nil {
+		errs = append(errs, fmt.Errorf("invalid hostname %q: %w. Ensure that the hostname is a valid DNS label", hostname, err))
+	}
+
+	// Validate ProxyGroup type
+	if pg.Spec.Type != tsapi.ProxyGroupTypeIngress {
+		errs = append(errs, fmt.Errorf("ProxyGroup %q is of type %q but must be of type %q",
+			pg.Name, pg.Spec.Type, tsapi.ProxyGroupTypeIngress))
+	}
+
+	// Validate ProxyGroup readiness
+	if !tsoperator.ProxyGroupIsReady(pg) {
+		errs = append(errs, fmt.Errorf("ProxyGroup %q is not ready", pg.Name))
+	}
+
+	return errors.Join(errs...)
+}
+
+// deleteVIPServiceIfExists attempts to delete the VIPService if it exists and is owned by the given Ingress.
+func (a *IngressPGReconciler) deleteVIPServiceIfExists(ctx context.Context, name string, ing *networkingv1.Ingress, logger *zap.SugaredLogger) error {
+	svc, err := a.getVIPService(ctx, name, logger)
+	if err != nil {
+		return fmt.Errorf("error getting VIPService: %w", err)
+	}
+
+	// isVIPServiceForIngress handles nil svc, so we don't need to check it here
+	if !isVIPServiceForIngress(svc, ing) {
+		return nil
+	}
+
+	logger.Infof("Deleting VIPService %q", name)
+	if err = a.tsClient.deleteVIPServiceByName(ctx, name); err != nil {
+		return fmt.Errorf("error deleting VIPService: %w", err)
+	}
+	return nil
+}

cmd/k8s-operator/ingress-for-pg_test.go

@@ -0,0 +1,337 @@
+// Copyright (c) Tailscale Inc & AUTHORS
+// SPDX-License-Identifier: BSD-3-Clause
+
+//go:build !plan9
+
+package main
+
+import (
+	"context"
+	"encoding/json"
+	"testing"
+
+	"slices"
+
+	"go.uber.org/zap"
+	corev1 "k8s.io/api/core/v1"
+	networkingv1 "k8s.io/api/networking/v1"
+	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
+	"k8s.io/apimachinery/pkg/types"
+	"k8s.io/client-go/tools/record"
+	"sigs.k8s.io/controller-runtime/pkg/client/fake"
+	"tailscale.com/ipn"
+	"tailscale.com/ipn/ipnstate"
+	tsapi "tailscale.com/k8s-operator/apis/v1alpha1"
+	"tailscale.com/types/ptr"
+)
+
+func TestIngressPGReconciler(t *testing.T) {
+	tsIngressClass := &networkingv1.IngressClass{
+		ObjectMeta: metav1.ObjectMeta{Name: "tailscale"},
+		Spec:       networkingv1.IngressClassSpec{Controller: "tailscale.com/ts-ingress"},
+	}
+
+	// Pre-create the ProxyGroup
+	pg := &tsapi.ProxyGroup{
+		ObjectMeta: metav1.ObjectMeta{
+			Name:       "test-pg",
+			Generation: 1,
+		},
+		Spec: tsapi.ProxyGroupSpec{
+			Type: tsapi.ProxyGroupTypeIngress,
+		},
+	}
+
+	// Pre-create the ConfigMap for the ProxyGroup
+	pgConfigMap := &corev1.ConfigMap{
+		ObjectMeta: metav1.ObjectMeta{
+			Name:      "test-pg-ingress-config",
+			Namespace: "operator-ns",
+		},
+		BinaryData: map[string][]byte{
+			"serve-config.json": []byte(`{"Services":{}}`),
+		},
+	}
+
+	fc := fake.NewClientBuilder().
+		WithScheme(tsapi.GlobalScheme).
+		WithObjects(pg, pgConfigMap, tsIngressClass).
+		WithStatusSubresource(pg).
+		Build()
+	mustUpdateStatus(t, fc, "", pg.Name, func(pg *tsapi.ProxyGroup) {
+		pg.Status.Conditions = []metav1.Condition{
+			{
+				Type:               string(tsapi.ProxyGroupReady),
+				Status:             metav1.ConditionTrue,
+				ObservedGeneration: 1,
+			},
+		}
+	})
+	ft := &fakeTSClient{}
+	fakeTsnetServer := &fakeTSNetServer{certDomains: []string{"foo.com"}}
+	zl, err := zap.NewDevelopment()
+	if err != nil {
+		t.Fatal(err)
+	}
+
+	lc := &fakeLocalClient{
+		status: &ipnstate.Status{
+			CurrentTailnet: &ipnstate.TailnetStatus{
+				MagicDNSSuffix: "ts.net",
+			},
+		},
+	}
+	ingPGR := &IngressPGReconciler{
+		Client:      fc,
+		tsClient:    ft,
+		tsnetServer: fakeTsnetServer,
+		defaultTags: []string{"tag:k8s"},
+		tsNamespace: "operator-ns",
+		logger:      zl.Sugar(),
+		recorder:    record.NewFakeRecorder(10),
+		lc:          lc,
+	}
+
+	// Test 1: Default tags
+	ing := &networkingv1.Ingress{
+		TypeMeta: metav1.TypeMeta{Kind: "Ingress", APIVersion: "networking.k8s.io/v1"},
+		ObjectMeta: metav1.ObjectMeta{
+			Name:      "test-ingress",
+			Namespace: "default",
+			UID:       types.UID("1234-UID"),
+			Annotations: map[string]string{
+				"tailscale.com/proxy-group": "test-pg",
+			},
+		},
+		Spec: networkingv1.IngressSpec{
+			IngressClassName: ptr.To("tailscale"),
+			DefaultBackend: &networkingv1.IngressBackend{
+				Service: &networkingv1.IngressServiceBackend{
+					Name: "test",
+					Port: networkingv1.ServiceBackendPort{
+						Number: 8080,
+					},
+				},
+			},
+			TLS: []networkingv1.IngressTLS{
+				{Hosts: []string{"my-svc.tailnetxyz.ts.net"}},
+			},
+		},
+	}
+	mustCreate(t, fc, ing)
+
+	// Verify initial reconciliation
+	expectReconciled(t, ingPGR, "default", "test-ingress")
+
+	// Get and verify the ConfigMap was updated
+	cm := &corev1.ConfigMap{}
+	if err := fc.Get(context.Background(), types.NamespacedName{
+		Name:      "test-pg-ingress-config",
+		Namespace: "operator-ns",
+	}, cm); err != nil {
+		t.Fatalf("getting ConfigMap: %v", err)
+	}
+
+	cfg := &ipn.ServeConfig{}
+	if err := json.Unmarshal(cm.BinaryData[serveConfigKey], cfg); err != nil {
+		t.Fatalf("unmarshaling serve config: %v", err)
+	}
+
+	if cfg.Services["svc:my-svc"] == nil {
+		t.Error("expected serve config to contain VIPService configuration")
+	}
+
+	// Verify VIPService uses default tags
+	vipSvc, err := ft.getVIPServiceByName(context.Background(), "my-svc")
+	if err != nil {
+		t.Fatalf("getting VIPService: %v", err)
+	}
+	if vipSvc == nil {
+		t.Fatal("VIPService not created")
+	}
+	wantTags := []string{"tag:k8s"} // default tags
+	if !slices.Equal(vipSvc.Tags, wantTags) {
+		t.Errorf("incorrect VIPService tags: got %v, want %v", vipSvc.Tags, wantTags)
+	}
+
+	// Test 2: Custom tags
+	mustUpdate(t, fc, "default", "test-ingress", func(ing *networkingv1.Ingress) {
+		ing.Annotations["tailscale.com/tags"] = "tag:custom,tag:test"
+	})
+	expectReconciled(t, ingPGR, "default", "test-ingress")
+
+	// Verify VIPService uses custom tags
+	vipSvc, err = ft.getVIPServiceByName(context.Background(), "my-svc")
+	if err != nil {
+		t.Fatalf("getting VIPService: %v", err)
+	}
+	if vipSvc == nil {
+		t.Fatal("VIPService not created")
+	}
+	wantTags = []string{"tag:custom", "tag:test"} // custom tags only
+	gotTags := slices.Clone(vipSvc.Tags)
+	slices.Sort(gotTags)
+	slices.Sort(wantTags)
+	if !slices.Equal(gotTags, wantTags) {
+		t.Errorf("incorrect VIPService tags: got %v, want %v", gotTags, wantTags)
+	}
+
+	// Delete the Ingress and verify cleanup
+	if err := fc.Delete(context.Background(), ing); err != nil {
+		t.Fatalf("deleting Ingress: %v", err)
+	}
+
+	expectReconciled(t, ingPGR, "default", "test-ingress")
+
+	// Verify the ConfigMap was cleaned up
+	cm = &corev1.ConfigMap{}
+	if err := fc.Get(context.Background(), types.NamespacedName{
+		Name:      "test-pg-ingress-config",
+		Namespace: "operator-ns",
+	}, cm); err != nil {
+		t.Fatalf("getting ConfigMap: %v", err)
+	}
+
+	cfg = &ipn.ServeConfig{}
+	if err := json.Unmarshal(cm.BinaryData[serveConfigKey], cfg); err != nil {
+		t.Fatalf("unmarshaling serve config: %v", err)
+	}
+
+	if len(cfg.Services) > 0 {
+		t.Error("serve config not cleaned up")
+	}
+}
+
+func TestValidateIngress(t *testing.T) {
+	baseIngress := &networkingv1.Ingress{
+		ObjectMeta: metav1.ObjectMeta{
+			Name:      "test-ingress",
+			Namespace: "default",
+		},
+	}
+
+	readyProxyGroup := &tsapi.ProxyGroup{
+		ObjectMeta: metav1.ObjectMeta{
+			Name:       "test-pg",
+			Generation: 1,
+		},
+		Spec: tsapi.ProxyGroupSpec{
+			Type: tsapi.ProxyGroupTypeIngress,
+		},
+		Status: tsapi.ProxyGroupStatus{
+			Conditions: []metav1.Condition{
+				{
+					Type:               string(tsapi.ProxyGroupReady),
+					Status:             metav1.ConditionTrue,
+					ObservedGeneration: 1,
+				},
+			},
+		},
+	}
+
+	tests := []struct {
+		name    string
+		ing     *networkingv1.Ingress
+		pg      *tsapi.ProxyGroup
+		wantErr string
+	}{
+		{
+			name: "valid_ingress_with_hostname",
+			ing: &networkingv1.Ingress{
+				ObjectMeta: baseIngress.ObjectMeta,
+				Spec: networkingv1.IngressSpec{
+					TLS: []networkingv1.IngressTLS{
+						{Hosts: []string{"test.example.com"}},
+					},
+				},
+			},
+			pg: readyProxyGroup,
+		},
+		{
+			name: "valid_ingress_with_default_hostname",
+			ing:  baseIngress,
+			pg:   readyProxyGroup,
+		},
+		{
+			name: "invalid_tags",
+			ing: &networkingv1.Ingress{
+				ObjectMeta: metav1.ObjectMeta{
+					Name:      baseIngress.Name,
+					Namespace: baseIngress.Namespace,
+					Annotations: map[string]string{
+						AnnotationTags: "tag:invalid!",
+					},
+				},
+			},
+			pg:      readyProxyGroup,
+			wantErr: "tailscale.com/tags annotation contains invalid tag \"tag:invalid!\": tag names can only contain numbers, letters, or dashes",
+		},
+		{
+			name: "multiple_TLS_entries",
+			ing: &networkingv1.Ingress{
+				ObjectMeta: baseIngress.ObjectMeta,
+				Spec: networkingv1.IngressSpec{
+					TLS: []networkingv1.IngressTLS{
+						{Hosts: []string{"test1.example.com"}},
+						{Hosts: []string{"test2.example.com"}},
+					},
+				},
+			},
+			pg:      readyProxyGroup,
+			wantErr: "Ingress contains invalid TLS block [{[test1.example.com] } {[test2.example.com] }]: only a single TLS entry with a single host is allowed",
+		},
+		{
+			name: "multiple_hosts_in_TLS_entry",
+			ing: &networkingv1.Ingress{
+				ObjectMeta: baseIngress.ObjectMeta,
+				Spec: networkingv1.IngressSpec{
+					TLS: []networkingv1.IngressTLS{
+						{Hosts: []string{"test1.example.com", "test2.example.com"}},
+					},
+				},
+			},
+			pg:      readyProxyGroup,
+			wantErr: "Ingress contains invalid TLS block [{[test1.example.com test2.example.com] }]: only a single TLS entry with a single host is allowed",
+		},
+		{
+			name: "wrong_proxy_group_type",
+			ing:  baseIngress,
+			pg: &tsapi.ProxyGroup{
+				ObjectMeta: readyProxyGroup.ObjectMeta,
+				Spec: tsapi.ProxyGroupSpec{
+					Type: tsapi.ProxyGroupType("foo"),
+				},
+				Status: readyProxyGroup.Status,
+			},
+			wantErr: "ProxyGroup \"test-pg\" is of type \"foo\" but must be of type \"ingress\"",
+		},
+		{
+			name: "proxy_group_not_ready",
+			ing:  baseIngress,
+			pg: &tsapi.ProxyGroup{
+				ObjectMeta: readyProxyGroup.ObjectMeta,
+				Spec:       readyProxyGroup.Spec,
+				Status: tsapi.ProxyGroupStatus{
+					Conditions: []metav1.Condition{
+						{
+							Type:               string(tsapi.ProxyGroupReady),
+							Status:             metav1.ConditionFalse,
+							ObservedGeneration: 1,
+						},
+					},
+				},
+			},
+			wantErr: "ProxyGroup \"test-pg\" is not ready",
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			r := &IngressPGReconciler{}
+			err := r.validateIngress(tt.ing, tt.pg)
+			if (err == nil && tt.wantErr != "") || (err != nil && err.Error() != tt.wantErr) {
+				t.Errorf("validateIngress() error = %v, wantErr %v", err, tt.wantErr)
+			}
+		})
+	}
+}

cmd/k8s-operator/ingress.go

@@ -26,6 +26,7 @@ import (
 	"tailscale.com/kube/kubetypes"
 	"tailscale.com/types/opt"
 	"tailscale.com/util/clientmetric"
+	"tailscale.com/util/mak"
 	"tailscale.com/util/set"
 )
 
@@ -58,7 +59,7 @@ var (
 )
 
 func (a *IngressReconciler) Reconcile(ctx context.Context, req reconcile.Request) (_ reconcile.Result, err error) {
-	logger := a.logger.With("ingress-ns", req.Namespace, "ingress-name", req.Name)
+	logger := a.logger.With("Ingress", req.NamespacedName)
 	logger.Debugf("starting reconcile")
 	defer logger.Debugf("reconcile finished")
 
@@ -76,7 +77,15 @@ func (a *IngressReconciler) Reconcile(ctx context.Context, req reconcile.Request
 		return reconcile.Result{}, a.maybeCleanup(ctx, logger, ing)
 	}
 
-	return reconcile.Result{}, a.maybeProvision(ctx, logger, ing)
+	if err := a.maybeProvision(ctx, logger, ing); err != nil {
+		if strings.Contains(err.Error(), optimisticLockErrorMsg) {
+			logger.Infof("optimistic lock error, retrying: %s", err)
+		} else {
+			return reconcile.Result{}, err
+		}
+	}
+
+	return reconcile.Result{}, nil
 }
 
 func (a *IngressReconciler) maybeCleanup(ctx context.Context, logger *zap.SugaredLogger, ing *networkingv1.Ingress) error {
@@ -90,7 +99,7 @@ func (a *IngressReconciler) maybeCleanup(ctx context.Context, logger *zap.Sugare
 		return nil
 	}
 
-	if done, err := a.ssr.Cleanup(ctx, logger, childResourceLabels(ing.Name, ing.Namespace, "ingress")); err != nil {
+	if done, err := a.ssr.Cleanup(ctx, logger, childResourceLabels(ing.Name, ing.Namespace, "ingress"), proxyTypeIngressResource); err != nil {
 		return fmt.Errorf("failed to cleanup: %w", err)
 	} else if !done {
 		logger.Debugf("cleanup not done yet, waiting for next reconcile")
@@ -120,9 +129,8 @@ func (a *IngressReconciler) maybeCleanup(ctx context.Context, logger *zap.Sugare
 // This function adds a finalizer to ing, ensuring that we can handle orderly
 // deprovisioning later.
 func (a *IngressReconciler) maybeProvision(ctx context.Context, logger *zap.SugaredLogger, ing *networkingv1.Ingress) error {
-	if err := a.validateIngressClass(ctx); err != nil {
+	if err := validateIngressClass(ctx, a.Client); err != nil {
 		logger.Warnf("error validating tailscale IngressClass: %v. In future this might be a terminal error.", err)
-
 	}
 	if !slices.Contains(ing.Finalizers, FinalizerName) {
 		// This log line is printed exactly once during initial provisioning,
@@ -151,7 +159,7 @@ func (a *IngressReconciler) maybeProvision(ctx context.Context, logger *zap.Suga
 	gaugeIngressResources.Set(int64(a.managedIngresses.Len()))
 	a.mu.Unlock()
 
-	if !a.ssr.IsHTTPSEnabledOnTailnet() {
+	if !IsHTTPSEnabledOnTailnet(a.ssr.tsnetServer) {
 		a.recorder.Event(ing, corev1.EventTypeWarning, "HTTPSNotEnabled", "HTTPS is not enabled on the tailnet; ingress may not work")
 	}
 
@@ -177,73 +185,16 @@ func (a *IngressReconciler) maybeProvision(ctx context.Context, logger *zap.Suga
 	}
 
 	web := sc.Web[magic443]
-	addIngressBackend := func(b *networkingv1.IngressBackend, path string) {
-		if b == nil {
-			return
-		}
-		if b.Service == nil {
-			a.recorder.Eventf(ing, corev1.EventTypeWarning, "InvalidIngressBackend", "backend for path %q is missing service", path)
-			return
-		}
-		var svc corev1.Service
-		if err := a.Get(ctx, types.NamespacedName{Namespace: ing.Namespace, Name: b.Service.Name}, &svc); err != nil {
-			a.recorder.Eventf(ing, corev1.EventTypeWarning, "InvalidIngressBackend", "failed to get service %q for path %q: %v", b.Service.Name, path, err)
-			return
-		}
-		if svc.Spec.ClusterIP == "" || svc.Spec.ClusterIP == "None" {
-			a.recorder.Eventf(ing, corev1.EventTypeWarning, "InvalidIngressBackend", "backend for path %q has invalid ClusterIP", path)
-			return
-		}
-		var port int32
-		if b.Service.Port.Name != "" {
-			for _, p := range svc.Spec.Ports {
-				if p.Name == b.Service.Port.Name {
-					port = p.Port
-					break
-				}
-			}
-		} else {
-			port = b.Service.Port.Number
-		}
-		if port == 0 {
-			a.recorder.Eventf(ing, corev1.EventTypeWarning, "InvalidIngressBackend", "backend for path %q has invalid port", path)
-			return
-		}
-		proto := "http://"
-		if port == 443 || b.Service.Port.Name == "https" {
-			proto = "https+insecure://"
-		}
-		web.Handlers[path] = &ipn.HTTPHandler{
-			Proxy: proto + svc.Spec.ClusterIP + ":" + fmt.Sprint(port) + path,
-		}
-	}
-	addIngressBackend(ing.Spec.DefaultBackend, "/")
 
 	var tlsHost string // hostname or FQDN or empty
 	if ing.Spec.TLS != nil && len(ing.Spec.TLS) > 0 && len(ing.Spec.TLS[0].Hosts) > 0 {
 		tlsHost = ing.Spec.TLS[0].Hosts[0]
 	}
-	for _, rule := range ing.Spec.Rules {
-		// Host is optional, but if it's present it must match the TLS host
-		// otherwise we ignore the rule.
-		if rule.Host != "" && rule.Host != tlsHost {
-			a.recorder.Eventf(ing, corev1.EventTypeWarning, "InvalidIngressBackend", "rule with host %q ignored, unsupported", rule.Host)
-			continue
-		}
-		for _, p := range rule.HTTP.Paths {
-			// Send a warning if folks use Exact path type - to make
-			// it easier for us to support Exact path type matching
-			// in the future if needed.
-			// https://kubernetes.io/docs/concepts/services-networking/ingress/#path-types
-			if *p.PathType == networkingv1.PathTypeExact {
-				msg := "Exact path type strict matching is currently not supported and requests will be routed as for Prefix path type. This behaviour might change in the future."
-				logger.Warnf(fmt.Sprintf("Unsupported Path type exact for path %s. %s", p.Path, msg))
-				a.recorder.Eventf(ing, corev1.EventTypeWarning, "UnsupportedPathTypeExact", msg)
-			}
-			addIngressBackend(&p.Backend, p.Path)
-		}
+	handlers, err := handlersForIngress(ctx, ing, a.Client, a.recorder, tlsHost, logger)
+	if err != nil {
+		return fmt.Errorf("failed to get handlers for ingress: %w", err)
 	}
-
+	web.Handlers = handlers
 	if len(web.Handlers) == 0 {
 		logger.Warn("Ingress contains no valid backends")
 		a.recorder.Eventf(ing, corev1.EventTypeWarning, "NoValidBackends", "no valid backends")
@@ -255,10 +206,7 @@ func (a *IngressReconciler) maybeProvision(ctx context.Context, logger *zap.Suga
 	if tstr, ok := ing.Annotations[AnnotationTags]; ok {
 		tags = strings.Split(tstr, ",")
 	}
-	hostname := ing.Namespace + "-" + ing.Name + "-ingress"
-	if tlsHost != "" {
-		hostname, _, _ = strings.Cut(tlsHost, ".")
-	}
+	hostname := hostnameForIngress(ing)
 
 	sts := &tailscaleSTSConfig{
 		Hostname:            hostname,
@@ -268,6 +216,7 @@ func (a *IngressReconciler) maybeProvision(ctx context.Context, logger *zap.Suga
 		Tags:                tags,
 		ChildResourceLabels: crl,
 		ProxyClassName:      proxyClass,
+		proxyType:           proxyTypeIngressResource,
 	}
 
 	if val := ing.GetAnnotations()[AnnotationExperimentalForwardClusterTrafficViaL7IngresProxy]; val == "true" {
@@ -278,12 +227,12 @@ func (a *IngressReconciler) maybeProvision(ctx context.Context, logger *zap.Suga
 		return fmt.Errorf("failed to provision: %w", err)
 	}
 
-	_, tsHost, _, err := a.ssr.DeviceInfo(ctx, crl)
+	dev, err := a.ssr.DeviceInfo(ctx, crl, logger)
 	if err != nil {
-		return fmt.Errorf("failed to get device ID: %w", err)
+		return fmt.Errorf("failed to retrieve Ingress HTTPS endpoint status: %w", err)
 	}
-	if tsHost == "" {
-		logger.Debugf("no Tailscale hostname known yet, waiting for proxy pod to finish auth")
+	if dev == nil || dev.ingressDNSName == "" {
+		logger.Debugf("no Ingress DNS name known yet, waiting for proxy Pod initialize and start serving Ingress")
 		// No hostname yet. Wait for the proxy pod to auth.
 		ing.Status.LoadBalancer.Ingress = nil
 		if err := a.Status().Update(ctx, ing); err != nil {
@@ -292,10 +241,10 @@ func (a *IngressReconciler) maybeProvision(ctx context.Context, logger *zap.Suga
 		return nil
 	}
 
-	logger.Debugf("setting ingress hostname to %q", tsHost)
+	logger.Debugf("setting Ingress hostname to %q", dev.ingressDNSName)
 	ing.Status.LoadBalancer.Ingress = []networkingv1.IngressLoadBalancerIngress{
 		{
-			Hostname: tsHost,
+			Hostname: dev.ingressDNSName,
 			Ports: []networkingv1.IngressPortStatus{
 				{
 					Protocol: "TCP",
@@ -313,28 +262,106 @@ func (a *IngressReconciler) maybeProvision(ctx context.Context, logger *zap.Suga
 func (a *IngressReconciler) shouldExpose(ing *networkingv1.Ingress) bool {
 	return ing != nil &&
 		ing.Spec.IngressClassName != nil &&
-		*ing.Spec.IngressClassName == tailscaleIngressClassName
+		*ing.Spec.IngressClassName == tailscaleIngressClassName &&
+		ing.Annotations[AnnotationProxyGroup] == ""
 }
 
 // validateIngressClass attempts to validate that 'tailscale' IngressClass
 // included in Tailscale installation manifests exists and has not been modified
 // to attempt to enable features that we do not support.
-func (a *IngressReconciler) validateIngressClass(ctx context.Context) error {
+func validateIngressClass(ctx context.Context, cl client.Client) error {
 	ic := &networkingv1.IngressClass{
 		ObjectMeta: metav1.ObjectMeta{
 			Name: tailscaleIngressClassName,
 		},
 	}
-	if err := a.Get(ctx, client.ObjectKeyFromObject(ic), ic); apierrors.IsNotFound(err) {
-		return errors.New("Tailscale IngressClass not found in cluster. Latest installation manifests include a tailscale IngressClass - please update")
+	if err := cl.Get(ctx, client.ObjectKeyFromObject(ic), ic); apierrors.IsNotFound(err) {
+		return errors.New("'tailscale' IngressClass not found in cluster.")
 	} else if err != nil {
 		return fmt.Errorf("error retrieving 'tailscale' IngressClass: %w", err)
 	}
 	if ic.Spec.Controller != tailscaleIngressControllerName {
-		return fmt.Errorf("Tailscale Ingress class controller name %s does not match tailscale Ingress controller name %s. Ensure that you are using 'tailscale' IngressClass from latest Tailscale installation manifests", ic.Spec.Controller, tailscaleIngressControllerName)
+		return fmt.Errorf("'tailscale' Ingress class controller name %s does not match tailscale Ingress controller name %s. Ensure that you are using 'tailscale' IngressClass from latest Tailscale installation manifests", ic.Spec.Controller, tailscaleIngressControllerName)
 	}
 	if ic.GetAnnotations()[ingressClassDefaultAnnotation] != "" {
 		return fmt.Errorf("%s annotation is set on 'tailscale' IngressClass, but Tailscale Ingress controller does not support default Ingress class. Ensure that you are using 'tailscale' IngressClass from latest Tailscale installation manifests", ingressClassDefaultAnnotation)
 	}
 	return nil
 }
+
+func handlersForIngress(ctx context.Context, ing *networkingv1.Ingress, cl client.Client, rec record.EventRecorder, tlsHost string, logger *zap.SugaredLogger) (handlers map[string]*ipn.HTTPHandler, err error) {
+	addIngressBackend := func(b *networkingv1.IngressBackend, path string) {
+		if b == nil {
+			return
+		}
+		if b.Service == nil {
+			rec.Eventf(ing, corev1.EventTypeWarning, "InvalidIngressBackend", "backend for path %q is missing service", path)
+			return
+		}
+		var svc corev1.Service
+		if err := cl.Get(ctx, types.NamespacedName{Namespace: ing.Namespace, Name: b.Service.Name}, &svc); err != nil {
+			rec.Eventf(ing, corev1.EventTypeWarning, "InvalidIngressBackend", "failed to get service %q for path %q: %v", b.Service.Name, path, err)
+			return
+		}
+		if svc.Spec.ClusterIP == "" || svc.Spec.ClusterIP == "None" {
+			rec.Eventf(ing, corev1.EventTypeWarning, "InvalidIngressBackend", "backend for path %q has invalid ClusterIP", path)
+			return
+		}
+		var port int32
+		if b.Service.Port.Name != "" {
+			for _, p := range svc.Spec.Ports {
+				if p.Name == b.Service.Port.Name {
+					port = p.Port
+					break
+				}
+			}
+		} else {
+			port = b.Service.Port.Number
+		}
+		if port == 0 {
+			rec.Eventf(ing, corev1.EventTypeWarning, "InvalidIngressBackend", "backend for path %q has invalid port", path)
+			return
+		}
+		proto := "http://"
+		if port == 443 || b.Service.Port.Name == "https" {
+			proto = "https+insecure://"
+		}
+		mak.Set(&handlers, path, &ipn.HTTPHandler{
+			Proxy: proto + svc.Spec.ClusterIP + ":" + fmt.Sprint(port) + path,
+		})
+	}
+	addIngressBackend(ing.Spec.DefaultBackend, "/")
+	for _, rule := range ing.Spec.Rules {
+		// Host is optional, but if it's present it must match the TLS host
+		// otherwise we ignore the rule.
+		if rule.Host != "" && rule.Host != tlsHost {
+			rec.Eventf(ing, corev1.EventTypeWarning, "InvalidIngressBackend", "rule with host %q ignored, unsupported", rule.Host)
+			continue
+		}
+		for _, p := range rule.HTTP.Paths {
+			// Send a warning if folks use Exact path type - to make
+			// it easier for us to support Exact path type matching
+			// in the future if needed.
+			// https://kubernetes.io/docs/concepts/services-networking/ingress/#path-types
+			if *p.PathType == networkingv1.PathTypeExact {
+				msg := "Exact path type strict matching is currently not supported and requests will be routed as for Prefix path type. This behaviour might change in the future."
+				logger.Warnf(fmt.Sprintf("Unsupported Path type exact for path %s. %s", p.Path, msg))
+				rec.Eventf(ing, corev1.EventTypeWarning, "UnsupportedPathTypeExact", msg)
+			}
+			addIngressBackend(&p.Backend, p.Path)
+		}
+	}
+	return handlers, nil
+}
+
+// hostnameForIngress returns the hostname for an Ingress resource.
+// If the Ingress has TLS configured with a host, it returns the first component of that host.
+// Otherwise, it returns a hostname derived from the Ingress name and namespace.
+func hostnameForIngress(ing *networkingv1.Ingress) string {
+	if ing.Spec.TLS != nil && len(ing.Spec.TLS) > 0 && len(ing.Spec.TLS[0].Hosts) > 0 {
+		h := ing.Spec.TLS[0].Hosts[0]
+		hostname, _, _ := strings.Cut(h, ".")
+		return hostname
+	}
+	return ing.Namespace + "-" + ing.Name + "-ingress"
+}

cmd/k8s-operator/ingress_test.go

@@ -12,6 +12,7 @@ import (
 	appsv1 "k8s.io/api/apps/v1"
 	corev1 "k8s.io/api/core/v1"
 	networkingv1 "k8s.io/api/networking/v1"
+	apiextensionsv1 "k8s.io/apiextensions-apiserver/pkg/apis/apiextensions/v1"
 	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
 	"k8s.io/apimachinery/pkg/types"
 	"sigs.k8s.io/controller-runtime/pkg/client/fake"
@@ -102,9 +103,9 @@ func TestTailscaleIngress(t *testing.T) {
 	}
 	opts.serveConfig = serveConfig
 
-	expectEqual(t, fc, expectedSecret(t, fc, opts), nil)
-	expectEqual(t, fc, expectedHeadlessService(shortName, "ingress"), nil)
-	expectEqual(t, fc, expectedSTSUserspace(t, fc, opts), removeHashAnnotation)
+	expectEqual(t, fc, expectedSecret(t, fc, opts))
+	expectEqual(t, fc, expectedHeadlessService(shortName, "ingress"))
+	expectEqual(t, fc, expectedSTSUserspace(t, fc, opts), removeHashAnnotation, removeResourceReqs)
 
 	// 2. Ingress status gets updated with ingress proxy's MagicDNS name
 	// once that becomes available.
@@ -119,7 +120,7 @@ func TestTailscaleIngress(t *testing.T) {
 			{Hostname: "foo.tailnetxyz.ts.net", Ports: []networkingv1.IngressPortStatus{{Port: 443, Protocol: "TCP"}}},
 		},
 	}
-	expectEqual(t, fc, ing, nil)
+	expectEqual(t, fc, ing)
 
 	// 3. Resources get created for Ingress that should allow forwarding
 	// cluster traffic
@@ -128,7 +129,7 @@ func TestTailscaleIngress(t *testing.T) {
 	})
 	opts.shouldEnableForwardingClusterTrafficViaIngress = true
 	expectReconciled(t, ingR, "default", "test")
-	expectEqual(t, fc, expectedSTS(t, fc, opts), removeHashAnnotation)
+	expectEqual(t, fc, expectedSTS(t, fc, opts), removeHashAnnotation, removeResourceReqs)
 
 	// 4. Resources get cleaned up when Ingress class is unset
 	mustUpdate(t, fc, "default", "test", func(ing *networkingv1.Ingress) {
@@ -141,12 +142,160 @@ func TestTailscaleIngress(t *testing.T) {
 	expectMissing[corev1.Secret](t, fc, "operator-ns", fullName)
 }
 
+func TestTailscaleIngressHostname(t *testing.T) {
+	tsIngressClass := &networkingv1.IngressClass{ObjectMeta: metav1.ObjectMeta{Name: "tailscale"}, Spec: networkingv1.IngressClassSpec{Controller: "tailscale.com/ts-ingress"}}
+	fc := fake.NewFakeClient(tsIngressClass)
+	ft := &fakeTSClient{}
+	fakeTsnetServer := &fakeTSNetServer{certDomains: []string{"foo.com"}}
+	zl, err := zap.NewDevelopment()
+	if err != nil {
+		t.Fatal(err)
+	}
+	ingR := &IngressReconciler{
+		Client: fc,
+		ssr: &tailscaleSTSReconciler{
+			Client:            fc,
+			tsClient:          ft,
+			tsnetServer:       fakeTsnetServer,
+			defaultTags:       []string{"tag:k8s"},
+			operatorNamespace: "operator-ns",
+			proxyImage:        "tailscale/tailscale",
+		},
+		logger: zl.Sugar(),
+	}
+
+	// 1. Resources get created for regular Ingress
+	ing := &networkingv1.Ingress{
+		TypeMeta: metav1.TypeMeta{Kind: "Ingress", APIVersion: "networking.k8s.io/v1"},
+		ObjectMeta: metav1.ObjectMeta{
+			Name:      "test",
+			Namespace: "default",
+			// The apiserver is supposed to set the UID, but the fake client
+			// doesn't. So, set it explicitly because other code later depends
+			// on it being set.
+			UID: types.UID("1234-UID"),
+		},
+		Spec: networkingv1.IngressSpec{
+			IngressClassName: ptr.To("tailscale"),
+			DefaultBackend: &networkingv1.IngressBackend{
+				Service: &networkingv1.IngressServiceBackend{
+					Name: "test",
+					Port: networkingv1.ServiceBackendPort{
+						Number: 8080,
+					},
+				},
+			},
+			TLS: []networkingv1.IngressTLS{
+				{Hosts: []string{"default-test"}},
+			},
+		},
+	}
+	mustCreate(t, fc, ing)
+	mustCreate(t, fc, &corev1.Service{
+		ObjectMeta: metav1.ObjectMeta{
+			Name:      "test",
+			Namespace: "default",
+		},
+		Spec: corev1.ServiceSpec{
+			ClusterIP: "1.2.3.4",
+			Ports: []corev1.ServicePort{{
+				Port: 8080,
+				Name: "http"},
+			},
+		},
+	})
+
+	expectReconciled(t, ingR, "default", "test")
+
+	fullName, shortName := findGenName(t, fc, "default", "test", "ingress")
+	mustCreate(t, fc, &corev1.Pod{
+		ObjectMeta: metav1.ObjectMeta{
+			Name:      fullName,
+			Namespace: "operator-ns",
+			UID:       "test-uid",
+		},
+	})
+	opts := configOpts{
+		stsName:    shortName,
+		secretName: fullName,
+		namespace:  "default",
+		parentType: "ingress",
+		hostname:   "default-test",
+		app:        kubetypes.AppIngressResource,
+	}
+	serveConfig := &ipn.ServeConfig{
+		TCP: map[uint16]*ipn.TCPPortHandler{443: {HTTPS: true}},
+		Web: map[ipn.HostPort]*ipn.WebServerConfig{"${TS_CERT_DOMAIN}:443": {Handlers: map[string]*ipn.HTTPHandler{"/": {Proxy: "http://1.2.3.4:8080/"}}}},
+	}
+	opts.serveConfig = serveConfig
+
+	expectEqual(t, fc, expectedSecret(t, fc, opts))
+	expectEqual(t, fc, expectedHeadlessService(shortName, "ingress"))
+	expectEqual(t, fc, expectedSTSUserspace(t, fc, opts), removeHashAnnotation, removeResourceReqs)
+
+	// 2. Ingress proxy with capability version >= 110 does not have an HTTPS endpoint set
+	mustUpdate(t, fc, "operator-ns", opts.secretName, func(secret *corev1.Secret) {
+		mak.Set(&secret.Data, "device_id", []byte("1234"))
+		mak.Set(&secret.Data, "tailscale_capver", []byte("110"))
+		mak.Set(&secret.Data, "pod_uid", []byte("test-uid"))
+		mak.Set(&secret.Data, "device_fqdn", []byte("foo.tailnetxyz.ts.net"))
+	})
+	expectReconciled(t, ingR, "default", "test")
+	ing.Finalizers = append(ing.Finalizers, "tailscale.com/finalizer")
+
+	expectEqual(t, fc, ing)
+
+	// 3. Ingress proxy with capability version >= 110 advertises HTTPS endpoint
+	mustUpdate(t, fc, "operator-ns", opts.secretName, func(secret *corev1.Secret) {
+		mak.Set(&secret.Data, "device_id", []byte("1234"))
+		mak.Set(&secret.Data, "tailscale_capver", []byte("110"))
+		mak.Set(&secret.Data, "pod_uid", []byte("test-uid"))
+		mak.Set(&secret.Data, "device_fqdn", []byte("foo.tailnetxyz.ts.net"))
+		mak.Set(&secret.Data, "https_endpoint", []byte("foo.tailnetxyz.ts.net"))
+	})
+	expectReconciled(t, ingR, "default", "test")
+	ing.Status.LoadBalancer = networkingv1.IngressLoadBalancerStatus{
+		Ingress: []networkingv1.IngressLoadBalancerIngress{
+			{Hostname: "foo.tailnetxyz.ts.net", Ports: []networkingv1.IngressPortStatus{{Port: 443, Protocol: "TCP"}}},
+		},
+	}
+	expectEqual(t, fc, ing)
+
+	// 4. Ingress proxy with capability version >= 110 does not have an HTTPS endpoint ready
+	mustUpdate(t, fc, "operator-ns", opts.secretName, func(secret *corev1.Secret) {
+		mak.Set(&secret.Data, "device_id", []byte("1234"))
+		mak.Set(&secret.Data, "tailscale_capver", []byte("110"))
+		mak.Set(&secret.Data, "pod_uid", []byte("test-uid"))
+		mak.Set(&secret.Data, "device_fqdn", []byte("foo.tailnetxyz.ts.net"))
+		mak.Set(&secret.Data, "https_endpoint", []byte("no-https"))
+	})
+	expectReconciled(t, ingR, "default", "test")
+	ing.Status.LoadBalancer.Ingress = nil
+	expectEqual(t, fc, ing)
+
+	// 5. Ingress proxy's state has https_endpoints set, but its capver is not matching Pod UID (downgrade)
+	mustUpdate(t, fc, "operator-ns", opts.secretName, func(secret *corev1.Secret) {
+		mak.Set(&secret.Data, "device_id", []byte("1234"))
+		mak.Set(&secret.Data, "tailscale_capver", []byte("110"))
+		mak.Set(&secret.Data, "pod_uid", []byte("not-the-right-uid"))
+		mak.Set(&secret.Data, "device_fqdn", []byte("foo.tailnetxyz.ts.net"))
+		mak.Set(&secret.Data, "https_endpoint", []byte("bar.tailnetxyz.ts.net"))
+	})
+	ing.Status.LoadBalancer = networkingv1.IngressLoadBalancerStatus{
+		Ingress: []networkingv1.IngressLoadBalancerIngress{
+			{Hostname: "foo.tailnetxyz.ts.net", Ports: []networkingv1.IngressPortStatus{{Port: 443, Protocol: "TCP"}}},
+		},
+	}
+	expectReconciled(t, ingR, "default", "test")
+	expectEqual(t, fc, ing)
+}
+
 func TestTailscaleIngressWithProxyClass(t *testing.T) {
 	// Setup
 	pc := &tsapi.ProxyClass{
 		ObjectMeta: metav1.ObjectMeta{Name: "custom-metadata"},
 		Spec: tsapi.ProxyClassSpec{StatefulSet: &tsapi.StatefulSet{
-			Labels:      map[string]string{"foo": "bar"},
+			Labels:      tsapi.Labels{"foo": "bar"},
 			Annotations: map[string]string{"bar.io/foo": "some-val"},
 			Pod:         &tsapi.Pod{Annotations: map[string]string{"foo.io/bar": "some-val"}}}},
 	}
@@ -234,9 +383,9 @@ func TestTailscaleIngressWithProxyClass(t *testing.T) {
 	}
 	opts.serveConfig = serveConfig
 
-	expectEqual(t, fc, expectedSecret(t, fc, opts), nil)
-	expectEqual(t, fc, expectedHeadlessService(shortName, "ingress"), nil)
-	expectEqual(t, fc, expectedSTSUserspace(t, fc, opts), removeHashAnnotation)
+	expectEqual(t, fc, expectedSecret(t, fc, opts))
+	expectEqual(t, fc, expectedHeadlessService(shortName, "ingress"))
+	expectEqual(t, fc, expectedSTSUserspace(t, fc, opts), removeHashAnnotation, removeResourceReqs)
 
 	// 2. Ingress is updated to specify a ProxyClass, ProxyClass is not yet
 	// ready, so proxy resource configuration does not change.
@@ -244,7 +393,7 @@ func TestTailscaleIngressWithProxyClass(t *testing.T) {
 		mak.Set(&ing.ObjectMeta.Labels, LabelProxyClass, "custom-metadata")
 	})
 	expectReconciled(t, ingR, "default", "test")
-	expectEqual(t, fc, expectedSTSUserspace(t, fc, opts), removeHashAnnotation)
+	expectEqual(t, fc, expectedSTSUserspace(t, fc, opts), removeHashAnnotation, removeResourceReqs)
 
 	// 3. ProxyClass is set to Ready by proxy-class reconciler. Ingress get
 	// reconciled and configuration from the ProxyClass is applied to the
@@ -259,7 +408,7 @@ func TestTailscaleIngressWithProxyClass(t *testing.T) {
 	})
 	expectReconciled(t, ingR, "default", "test")
 	opts.proxyClass = pc.Name
-	expectEqual(t, fc, expectedSTSUserspace(t, fc, opts), removeHashAnnotation)
+	expectEqual(t, fc, expectedSTSUserspace(t, fc, opts), removeHashAnnotation, removeResourceReqs)
 
 	// 4. tailscale.com/proxy-class label is removed from the Ingress, the
 	// Ingress gets reconciled and the custom ProxyClass configuration is
@@ -269,5 +418,145 @@ func TestTailscaleIngressWithProxyClass(t *testing.T) {
 	})
 	expectReconciled(t, ingR, "default", "test")
 	opts.proxyClass = ""
-	expectEqual(t, fc, expectedSTSUserspace(t, fc, opts), removeHashAnnotation)
+	expectEqual(t, fc, expectedSTSUserspace(t, fc, opts), removeHashAnnotation, removeResourceReqs)
+}
+
+func TestTailscaleIngressWithServiceMonitor(t *testing.T) {
+	pc := &tsapi.ProxyClass{
+		ObjectMeta: metav1.ObjectMeta{Name: "metrics", Generation: 1},
+		Spec:       tsapi.ProxyClassSpec{},
+		Status: tsapi.ProxyClassStatus{
+			Conditions: []metav1.Condition{{
+				Status:             metav1.ConditionTrue,
+				Type:               string(tsapi.ProxyClassReady),
+				ObservedGeneration: 1,
+			}}},
+	}
+	ing := &networkingv1.Ingress{
+		TypeMeta: metav1.TypeMeta{Kind: "Ingress", APIVersion: "networking.k8s.io/v1"},
+		ObjectMeta: metav1.ObjectMeta{
+			Name:      "test",
+			Namespace: "default",
+			// The apiserver is supposed to set the UID, but the fake client
+			// doesn't. So, set it explicitly because other code later depends
+			// on it being set.
+			UID: types.UID("1234-UID"),
+			Labels: map[string]string{
+				"tailscale.com/proxy-class": "metrics",
+			},
+		},
+		Spec: networkingv1.IngressSpec{
+			IngressClassName: ptr.To("tailscale"),
+			DefaultBackend: &networkingv1.IngressBackend{
+				Service: &networkingv1.IngressServiceBackend{
+					Name: "test",
+					Port: networkingv1.ServiceBackendPort{
+						Number: 8080,
+					},
+				},
+			},
+			TLS: []networkingv1.IngressTLS{
+				{Hosts: []string{"default-test"}},
+			},
+		},
+	}
+	svc := &corev1.Service{
+		ObjectMeta: metav1.ObjectMeta{
+			Name:      "test",
+			Namespace: "default",
+		},
+		Spec: corev1.ServiceSpec{
+			ClusterIP: "1.2.3.4",
+			Ports: []corev1.ServicePort{{
+				Port: 8080,
+				Name: "http"},
+			},
+		},
+	}
+	crd := &apiextensionsv1.CustomResourceDefinition{ObjectMeta: metav1.ObjectMeta{Name: serviceMonitorCRD}}
+	tsIngressClass := &networkingv1.IngressClass{ObjectMeta: metav1.ObjectMeta{Name: "tailscale"}, Spec: networkingv1.IngressClassSpec{Controller: "tailscale.com/ts-ingress"}}
+	fc := fake.NewClientBuilder().
+		WithScheme(tsapi.GlobalScheme).
+		WithObjects(pc, tsIngressClass, ing, svc).
+		WithStatusSubresource(pc).
+		Build()
+	ft := &fakeTSClient{}
+	fakeTsnetServer := &fakeTSNetServer{certDomains: []string{"foo.com"}}
+	zl, err := zap.NewDevelopment()
+	if err != nil {
+		t.Fatal(err)
+	}
+	ingR := &IngressReconciler{
+		Client: fc,
+		ssr: &tailscaleSTSReconciler{
+			Client:            fc,
+			tsClient:          ft,
+			tsnetServer:       fakeTsnetServer,
+			defaultTags:       []string{"tag:k8s"},
+			operatorNamespace: "operator-ns",
+			proxyImage:        "tailscale/tailscale",
+		},
+		logger: zl.Sugar(),
+	}
+	expectReconciled(t, ingR, "default", "test")
+	fullName, shortName := findGenName(t, fc, "default", "test", "ingress")
+	serveConfig := &ipn.ServeConfig{
+		TCP: map[uint16]*ipn.TCPPortHandler{443: {HTTPS: true}},
+		Web: map[ipn.HostPort]*ipn.WebServerConfig{"${TS_CERT_DOMAIN}:443": {Handlers: map[string]*ipn.HTTPHandler{"/": {Proxy: "http://1.2.3.4:8080/"}}}},
+	}
+	opts := configOpts{
+		stsName:            shortName,
+		secretName:         fullName,
+		namespace:          "default",
+		tailscaleNamespace: "operator-ns",
+		parentType:         "ingress",
+		hostname:           "default-test",
+		app:                kubetypes.AppIngressResource,
+		namespaced:         true,
+		proxyType:          proxyTypeIngressResource,
+		serveConfig:        serveConfig,
+		resourceVersion:    "1",
+	}
+
+	// 1. Enable metrics- expect metrics Service to be created
+	mustUpdate(t, fc, "", "metrics", func(proxyClass *tsapi.ProxyClass) {
+		proxyClass.Spec.Metrics = &tsapi.Metrics{Enable: true}
+	})
+	opts.enableMetrics = true
+
+	expectReconciled(t, ingR, "default", "test")
+
+	expectEqual(t, fc, expectedMetricsService(opts))
+
+	// 2. Enable ServiceMonitor - should not error when there is no ServiceMonitor CRD in cluster
+	mustUpdate(t, fc, "", "metrics", func(pc *tsapi.ProxyClass) {
+		pc.Spec.Metrics.ServiceMonitor = &tsapi.ServiceMonitor{Enable: true, Labels: tsapi.Labels{"foo": "bar"}}
+	})
+	expectReconciled(t, ingR, "default", "test")
+	expectEqual(t, fc, expectedMetricsService(opts))
+
+	// 3. Create ServiceMonitor CRD and reconcile- ServiceMonitor should get created
+	mustCreate(t, fc, crd)
+	expectReconciled(t, ingR, "default", "test")
+	opts.serviceMonitorLabels = tsapi.Labels{"foo": "bar"}
+	expectEqual(t, fc, expectedMetricsService(opts))
+	expectEqualUnstructured(t, fc, expectedServiceMonitor(t, opts))
+
+	// 4. Update ServiceMonitor CRD and reconcile- ServiceMonitor should get updated
+	mustUpdate(t, fc, pc.Namespace, pc.Name, func(proxyClass *tsapi.ProxyClass) {
+		proxyClass.Spec.Metrics.ServiceMonitor.Labels = nil
+	})
+	expectReconciled(t, ingR, "default", "test")
+	opts.serviceMonitorLabels = nil
+	opts.resourceVersion = "2"
+	expectEqual(t, fc, expectedMetricsService(opts))
+	expectEqualUnstructured(t, fc, expectedServiceMonitor(t, opts))
+
+	// 5. Disable metrics - metrics resources should get deleted.
+	mustUpdate(t, fc, pc.Namespace, pc.Name, func(proxyClass *tsapi.ProxyClass) {
+		proxyClass.Spec.Metrics = nil
+	})
+	expectReconciled(t, ingR, "default", "test")
+	expectMissing[corev1.Service](t, fc, "operator-ns", metricsResourceName(shortName))
+	// ServiceMonitor gets garbage collected when the Service is deleted - we cannot test that here.
 }

cmd/k8s-operator/metrics_resources.go

@@ -0,0 +1,295 @@
+// Copyright (c) Tailscale Inc & AUTHORS
+// SPDX-License-Identifier: BSD-3-Clause
+
+//go:build !plan9
+
+package main
+
+import (
+	"context"
+	"fmt"
+	"reflect"
+
+	"go.uber.org/zap"
+	corev1 "k8s.io/api/core/v1"
+	apierrors "k8s.io/apimachinery/pkg/api/errors"
+	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
+	"k8s.io/apimachinery/pkg/apis/meta/v1/unstructured"
+	"k8s.io/apimachinery/pkg/runtime"
+	"k8s.io/apimachinery/pkg/types"
+	"sigs.k8s.io/controller-runtime/pkg/client"
+	tsapi "tailscale.com/k8s-operator/apis/v1alpha1"
+)
+
+const (
+	labelMetricsTarget = "tailscale.com/metrics-target"
+
+	// These labels get transferred from the metrics Service to the ingested Prometheus metrics.
+	labelPromProxyType            = "ts_proxy_type"
+	labelPromProxyParentName      = "ts_proxy_parent_name"
+	labelPromProxyParentNamespace = "ts_proxy_parent_namespace"
+	labelPromJob                  = "ts_prom_job"
+
+	serviceMonitorCRD = "servicemonitors.monitoring.coreos.com"
+)
+
+// ServiceMonitor contains a subset of fields of servicemonitors.monitoring.coreos.com Custom Resource Definition.
+// Duplicating it here allows us to avoid importing prometheus-operator library.
+// https://github.com/prometheus-operator/prometheus-operator/blob/bb4514e0d5d69f20270e29cfd4ad39b87865ccdf/pkg/apis/monitoring/v1/servicemonitor_types.go#L40
+type ServiceMonitor struct {
+	metav1.TypeMeta   `json:",inline"`
+	metav1.ObjectMeta `json:"metadata"`
+	Spec              ServiceMonitorSpec `json:"spec"`
+}
+
+// https://github.com/prometheus-operator/prometheus-operator/blob/bb4514e0d5d69f20270e29cfd4ad39b87865ccdf/pkg/apis/monitoring/v1/servicemonitor_types.go#L55
+type ServiceMonitorSpec struct {
+	// Endpoints defines the endpoints to be scraped on the selected Service(s).
+	// https://github.com/prometheus-operator/prometheus-operator/blob/bb4514e0d5d69f20270e29cfd4ad39b87865ccdf/pkg/apis/monitoring/v1/servicemonitor_types.go#L82
+	Endpoints []ServiceMonitorEndpoint `json:"endpoints"`
+	// JobLabel is the label on the Service whose value will become the value of the Prometheus job label for the metrics ingested via this ServiceMonitor.
+	// https://github.com/prometheus-operator/prometheus-operator/blob/bb4514e0d5d69f20270e29cfd4ad39b87865ccdf/pkg/apis/monitoring/v1/servicemonitor_types.go#L66
+	JobLabel string `json:"jobLabel"`
+	// NamespaceSelector selects the namespace of Service(s) that this ServiceMonitor allows to scrape.
+	// https://github.com/prometheus-operator/prometheus-operator/blob/bb4514e0d5d69f20270e29cfd4ad39b87865ccdf/pkg/apis/monitoring/v1/servicemonitor_types.go#L88
+	NamespaceSelector ServiceMonitorNamespaceSelector `json:"namespaceSelector,omitempty"`
+	// Selector is the label selector for Service(s) that this ServiceMonitor allows to scrape.
+	// https://github.com/prometheus-operator/prometheus-operator/blob/bb4514e0d5d69f20270e29cfd4ad39b87865ccdf/pkg/apis/monitoring/v1/servicemonitor_types.go#L85
+	Selector metav1.LabelSelector `json:"selector"`
+	// TargetLabels are labels on the selected Service that should be applied as Prometheus labels to the ingested metrics.
+	// https://github.com/prometheus-operator/prometheus-operator/blob/bb4514e0d5d69f20270e29cfd4ad39b87865ccdf/pkg/apis/monitoring/v1/servicemonitor_types.go#L72
+	TargetLabels []string `json:"targetLabels"`
+}
+
+// ServiceMonitorNamespaceSelector selects namespaces in which Prometheus operator will attempt to find Services for
+// this ServiceMonitor.
+// https://github.com/prometheus-operator/prometheus-operator/blob/bb4514e0d5d69f20270e29cfd4ad39b87865ccdf/pkg/apis/monitoring/v1/servicemonitor_types.go#L88
+type ServiceMonitorNamespaceSelector struct {
+	MatchNames []string `json:"matchNames,omitempty"`
+}
+
+// ServiceMonitorEndpoint defines an endpoint of Service to scrape. We only define port here. Prometheus by default
+// scrapes /metrics path, which is what we want.
+type ServiceMonitorEndpoint struct {
+	// Port is the name of the Service port that Prometheus will scrape.
+	Port string `json:"port,omitempty"`
+}
+
+func reconcileMetricsResources(ctx context.Context, logger *zap.SugaredLogger, opts *metricsOpts, pc *tsapi.ProxyClass, cl client.Client) error {
+	if opts.proxyType == proxyTypeEgress {
+		// Metrics are currently not being enabled for standalone egress proxies.
+		return nil
+	}
+	if pc == nil || pc.Spec.Metrics == nil || !pc.Spec.Metrics.Enable {
+		return maybeCleanupMetricsResources(ctx, opts, cl)
+	}
+	metricsSvc := &corev1.Service{
+		ObjectMeta: metav1.ObjectMeta{
+			Name:      metricsResourceName(opts.proxyStsName),
+			Namespace: opts.tsNamespace,
+			Labels:    metricsResourceLabels(opts),
+		},
+		Spec: corev1.ServiceSpec{
+			Selector: opts.proxyLabels,
+			Type:     corev1.ServiceTypeClusterIP,
+			Ports:    []corev1.ServicePort{{Protocol: "TCP", Port: 9002, Name: "metrics"}},
+		},
+	}
+	var err error
+	metricsSvc, err = createOrUpdate(ctx, cl, opts.tsNamespace, metricsSvc, func(svc *corev1.Service) {
+		svc.Spec.Ports = metricsSvc.Spec.Ports
+		svc.Spec.Selector = metricsSvc.Spec.Selector
+	})
+	if err != nil {
+		return fmt.Errorf("error ensuring metrics Service: %w", err)
+	}
+
+	crdExists, err := hasServiceMonitorCRD(ctx, cl)
+	if err != nil {
+		return fmt.Errorf("error verifying that %q CRD exists: %w", serviceMonitorCRD, err)
+	}
+	if !crdExists {
+		return nil
+	}
+
+	if pc.Spec.Metrics.ServiceMonitor == nil || !pc.Spec.Metrics.ServiceMonitor.Enable {
+		return maybeCleanupServiceMonitor(ctx, cl, opts.proxyStsName, opts.tsNamespace)
+	}
+
+	logger.Infof("ensuring ServiceMonitor for metrics Service %s/%s", metricsSvc.Namespace, metricsSvc.Name)
+	svcMonitor, err := newServiceMonitor(metricsSvc, pc.Spec.Metrics.ServiceMonitor)
+	if err != nil {
+		return fmt.Errorf("error creating ServiceMonitor: %w", err)
+	}
+
+	// We don't use createOrUpdate here because that does not work with unstructured types.
+	existing := svcMonitor.DeepCopy()
+	err = cl.Get(ctx, client.ObjectKeyFromObject(metricsSvc), existing)
+	if apierrors.IsNotFound(err) {
+		if err := cl.Create(ctx, svcMonitor); err != nil {
+			return fmt.Errorf("error creating ServiceMonitor: %w", err)
+		}
+		return nil
+	}
+	if err != nil {
+		return fmt.Errorf("error getting ServiceMonitor: %w", err)
+	}
+	// Currently, we only update labels on the ServiceMonitor as those are the only values that can change.
+	if !reflect.DeepEqual(existing.GetLabels(), svcMonitor.GetLabels()) {
+		existing.SetLabels(svcMonitor.GetLabels())
+		if err := cl.Update(ctx, existing); err != nil {
+			return fmt.Errorf("error updating ServiceMonitor: %w", err)
+		}
+	}
+	return nil
+}
+
+// maybeCleanupMetricsResources ensures that any metrics resources created for a proxy are deleted. Only metrics Service
+// gets deleted explicitly because the ServiceMonitor has Service's owner reference, so gets garbage collected
+// automatically.
+func maybeCleanupMetricsResources(ctx context.Context, opts *metricsOpts, cl client.Client) error {
+	sel := metricsSvcSelector(opts.proxyLabels, opts.proxyType)
+	return cl.DeleteAllOf(ctx, &corev1.Service{}, client.InNamespace(opts.tsNamespace), client.MatchingLabels(sel))
+}
+
+// maybeCleanupServiceMonitor cleans up any ServiceMonitor created for the named proxy StatefulSet.
+func maybeCleanupServiceMonitor(ctx context.Context, cl client.Client, stsName, ns string) error {
+	smName := metricsResourceName(stsName)
+	sm := serviceMonitorTemplate(smName, ns)
+	u, err := serviceMonitorToUnstructured(sm)
+	if err != nil {
+		return fmt.Errorf("error building ServiceMonitor: %w", err)
+	}
+	err = cl.Get(ctx, types.NamespacedName{Name: smName, Namespace: ns}, u)
+	if apierrors.IsNotFound(err) {
+		return nil // nothing to do
+	}
+	if err != nil {
+		return fmt.Errorf("error verifying if ServiceMonitor %s/%s exists: %w", ns, stsName, err)
+	}
+	return cl.Delete(ctx, u)
+}
+
+// newServiceMonitor takes a metrics Service created for a proxy and constructs and returns a ServiceMonitor for that
+// proxy that can be applied to the kube API server.
+// The ServiceMonitor is returned as Unstructured type - this allows us to avoid importing prometheus-operator API server client/schema.
+func newServiceMonitor(metricsSvc *corev1.Service, spec *tsapi.ServiceMonitor) (*unstructured.Unstructured, error) {
+	sm := serviceMonitorTemplate(metricsSvc.Name, metricsSvc.Namespace)
+	sm.ObjectMeta.Labels = metricsSvc.Labels
+	if spec != nil && len(spec.Labels) > 0 {
+		sm.ObjectMeta.Labels = mergeMapKeys(sm.ObjectMeta.Labels, spec.Labels.Parse())
+	}
+
+	sm.ObjectMeta.OwnerReferences = []metav1.OwnerReference{*metav1.NewControllerRef(metricsSvc, corev1.SchemeGroupVersion.WithKind("Service"))}
+	sm.Spec = ServiceMonitorSpec{
+		Selector: metav1.LabelSelector{MatchLabels: metricsSvc.Labels},
+		Endpoints: []ServiceMonitorEndpoint{{
+			Port: "metrics",
+		}},
+		NamespaceSelector: ServiceMonitorNamespaceSelector{
+			MatchNames: []string{metricsSvc.Namespace},
+		},
+		JobLabel: labelPromJob,
+		TargetLabels: []string{
+			labelPromProxyParentName,
+			labelPromProxyParentNamespace,
+			labelPromProxyType,
+		},
+	}
+	return serviceMonitorToUnstructured(sm)
+}
+
+// serviceMonitorToUnstructured takes a ServiceMonitor and converts it to Unstructured type that can be used by the c/r
+// client in Kubernetes API server calls.
+func serviceMonitorToUnstructured(sm *ServiceMonitor) (*unstructured.Unstructured, error) {
+	contents, err := runtime.DefaultUnstructuredConverter.ToUnstructured(sm)
+	if err != nil {
+		return nil, fmt.Errorf("error converting ServiceMonitor to Unstructured: %w", err)
+	}
+	u := &unstructured.Unstructured{}
+	u.SetUnstructuredContent(contents)
+	u.SetGroupVersionKind(sm.GroupVersionKind())
+	return u, nil
+}
+
+// metricsResourceName returns name for metrics Service and ServiceMonitor for a proxy StatefulSet.
+func metricsResourceName(stsName string) string {
+	// Maximum length of StatefulSet name if 52 chars, so this is fine.
+	return fmt.Sprintf("%s-metrics", stsName)
+}
+
+// metricsResourceLabels constructs labels that will be applied to metrics Service and metrics ServiceMonitor for a
+// proxy.
+func metricsResourceLabels(opts *metricsOpts) map[string]string {
+	lbls := map[string]string{
+		LabelManaged:             "true",
+		labelMetricsTarget:       opts.proxyStsName,
+		labelPromProxyType:       opts.proxyType,
+		labelPromProxyParentName: opts.proxyLabels[LabelParentName],
+	}
+	// Include namespace label for proxies created for a namespaced type.
+	if isNamespacedProxyType(opts.proxyType) {
+		lbls[labelPromProxyParentNamespace] = opts.proxyLabels[LabelParentNamespace]
+	}
+	lbls[labelPromJob] = promJobName(opts)
+	return lbls
+}
+
+// promJobName constructs the value of the Prometheus job label that will apply to all metrics for a ServiceMonitor.
+func promJobName(opts *metricsOpts) string {
+	// Include parent resource namespace for proxies created for namespaced types.
+	if opts.proxyType == proxyTypeIngressResource || opts.proxyType == proxyTypeIngressService {
+		return fmt.Sprintf("ts_%s_%s_%s", opts.proxyType, opts.proxyLabels[LabelParentNamespace], opts.proxyLabels[LabelParentName])
+	}
+	return fmt.Sprintf("ts_%s_%s", opts.proxyType, opts.proxyLabels[LabelParentName])
+}
+
+// metricsSvcSelector returns the minimum label set to uniquely identify a metrics Service for a proxy.
+func metricsSvcSelector(proxyLabels map[string]string, proxyType string) map[string]string {
+	sel := map[string]string{
+		labelPromProxyType:       proxyType,
+		labelPromProxyParentName: proxyLabels[LabelParentName],
+	}
+	// Include namespace label for proxies created for a namespaced type.
+	if isNamespacedProxyType(proxyType) {
+		sel[labelPromProxyParentNamespace] = proxyLabels[LabelParentNamespace]
+	}
+	return sel
+}
+
+// serviceMonitorTemplate returns a base ServiceMonitor type that, when converted to Unstructured, is a valid type that
+// can be used in kube API server calls via the c/r client.
+func serviceMonitorTemplate(name, ns string) *ServiceMonitor {
+	return &ServiceMonitor{
+		TypeMeta: metav1.TypeMeta{
+			Kind:       "ServiceMonitor",
+			APIVersion: "monitoring.coreos.com/v1",
+		},
+		ObjectMeta: metav1.ObjectMeta{
+			Name:      name,
+			Namespace: ns,
+		},
+	}
+}
+
+type metricsOpts struct {
+	proxyStsName string            // name of StatefulSet for proxy
+	tsNamespace  string            // namespace in which Tailscale is installed
+	proxyLabels  map[string]string // labels of the proxy StatefulSet
+	proxyType    string
+}
+
+func isNamespacedProxyType(typ string) bool {
+	return typ == proxyTypeIngressResource || typ == proxyTypeIngressService
+}
+
+func mergeMapKeys(a, b map[string]string) map[string]string {
+	m := make(map[string]string, len(a)+len(b))
+	for key, val := range b {
+		m[key] = val
+	}
+	for key, val := range a {
+		m[key] = val
+	}
+	return m
+}

cmd/k8s-operator/nameserver.go

@@ -9,6 +9,7 @@ import (
 	"context"
 	"fmt"
 	"slices"
+	"strings"
 	"sync"
 
 	_ "embed"
@@ -86,7 +87,7 @@ func (a *NameserverReconciler) Reconcile(ctx context.Context, req reconcile.Requ
 			return reconcile.Result{}, nil
 		}
 		logger.Info("Cleaning up DNSConfig resources")
-		if err := a.maybeCleanup(ctx, &dnsCfg, logger); err != nil {
+		if err := a.maybeCleanup(&dnsCfg); err != nil {
 			logger.Errorf("error cleaning up reconciler resource: %v", err)
 			return res, err
 		}
@@ -100,9 +101,9 @@ func (a *NameserverReconciler) Reconcile(ctx context.Context, req reconcile.Requ
 	}
 
 	oldCnStatus := dnsCfg.Status.DeepCopy()
-	setStatus := func(dnsCfg *tsapi.DNSConfig, conditionType tsapi.ConditionType, status metav1.ConditionStatus, reason, message string) (reconcile.Result, error) {
+	setStatus := func(dnsCfg *tsapi.DNSConfig, status metav1.ConditionStatus, reason, message string) (reconcile.Result, error) {
 		tsoperator.SetDNSConfigCondition(dnsCfg, tsapi.NameserverReady, status, reason, message, dnsCfg.Generation, a.clock, logger)
-		if !apiequality.Semantic.DeepEqual(oldCnStatus, dnsCfg.Status) {
+		if !apiequality.Semantic.DeepEqual(oldCnStatus, &dnsCfg.Status) {
 			// An error encountered here should get returned by the Reconcile function.
 			if updateErr := a.Client.Status().Update(ctx, dnsCfg); updateErr != nil {
 				err = errors.Wrap(err, updateErr.Error())
@@ -118,7 +119,7 @@ func (a *NameserverReconciler) Reconcile(ctx context.Context, req reconcile.Requ
 		msg := "invalid cluster configuration: more than one tailscale.com/dnsconfigs found. Please ensure that no more than one is created."
 		logger.Error(msg)
 		a.recorder.Event(&dnsCfg, corev1.EventTypeWarning, reasonMultipleDNSConfigsPresent, messageMultipleDNSConfigsPresent)
-		setStatus(&dnsCfg, tsapi.NameserverReady, metav1.ConditionFalse, reasonMultipleDNSConfigsPresent, messageMultipleDNSConfigsPresent)
+		setStatus(&dnsCfg, metav1.ConditionFalse, reasonMultipleDNSConfigsPresent, messageMultipleDNSConfigsPresent)
 	}
 
 	if !slices.Contains(dnsCfg.Finalizers, FinalizerName) {
@@ -127,11 +128,16 @@ func (a *NameserverReconciler) Reconcile(ctx context.Context, req reconcile.Requ
 		if err := a.Update(ctx, &dnsCfg); err != nil {
 			msg := fmt.Sprintf(messageNameserverCreationFailed, err)
 			logger.Error(msg)
-			return setStatus(&dnsCfg, tsapi.NameserverReady, metav1.ConditionFalse, reasonNameserverCreationFailed, msg)
+			return setStatus(&dnsCfg, metav1.ConditionFalse, reasonNameserverCreationFailed, msg)
 		}
 	}
 	if err := a.maybeProvision(ctx, &dnsCfg, logger); err != nil {
-		return reconcile.Result{}, fmt.Errorf("error provisioning nameserver resources: %w", err)
+		if strings.Contains(err.Error(), optimisticLockErrorMsg) {
+			logger.Infof("optimistic lock error, retrying: %s", err)
+			return reconcile.Result{}, nil
+		} else {
+			return reconcile.Result{}, fmt.Errorf("error provisioning nameserver resources: %w", err)
+		}
 	}
 
 	a.mu.Lock()
@@ -149,7 +155,7 @@ func (a *NameserverReconciler) Reconcile(ctx context.Context, req reconcile.Requ
 		dnsCfg.Status.Nameserver = &tsapi.NameserverStatus{
 			IP: ip,
 		}
-		return setStatus(&dnsCfg, tsapi.NameserverReady, metav1.ConditionTrue, reasonNameserverCreated, reasonNameserverCreated)
+		return setStatus(&dnsCfg, metav1.ConditionTrue, reasonNameserverCreated, reasonNameserverCreated)
 	}
 	logger.Info("nameserver Service does not have an IP address allocated, waiting...")
 	return reconcile.Result{}, nil
@@ -188,7 +194,7 @@ func (a *NameserverReconciler) maybeProvision(ctx context.Context, tsDNSCfg *tsa
 // maybeCleanup removes DNSConfig from being tracked. The cluster resources
 // created, will be automatically garbage collected as they are owned by the
 // DNSConfig.
-func (a *NameserverReconciler) maybeCleanup(ctx context.Context, dnsCfg *tsapi.DNSConfig, logger *zap.SugaredLogger) error {
+func (a *NameserverReconciler) maybeCleanup(dnsCfg *tsapi.DNSConfig) error {
 	a.mu.Lock()
 	a.managedNameservers.Remove(dnsCfg.UID)
 	a.mu.Unlock()

cmd/k8s-operator/nameserver_test.go

@@ -69,7 +69,7 @@ func TestNameserverReconciler(t *testing.T) {
 	wantsDeploy.Namespace = "tailscale"
 	labels := nameserverResourceLabels("test", "tailscale")
 	wantsDeploy.ObjectMeta.Labels = labels
-	expectEqual(t, fc, wantsDeploy, nil)
+	expectEqual(t, fc, wantsDeploy)
 
 	// Verify that DNSConfig advertizes the nameserver's Service IP address,
 	// has the ready status condition and tailscale finalizer.
@@ -88,7 +88,7 @@ func TestNameserverReconciler(t *testing.T) {
 		Message:            reasonNameserverCreated,
 		LastTransitionTime: metav1.Time{Time: cl.Now().Truncate(time.Second)},
 	})
-	expectEqual(t, fc, dnsCfg, nil)
+	expectEqual(t, fc, dnsCfg)
 
 	// // Verify that nameserver image gets updated to match DNSConfig spec.
 	mustUpdate(t, fc, "", "test", func(dnsCfg *tsapi.DNSConfig) {
@@ -96,7 +96,7 @@ func TestNameserverReconciler(t *testing.T) {
 	})
 	expectReconciled(t, nr, "", "test")
 	wantsDeploy.Spec.Template.Spec.Containers[0].Image = "test:v0.0.2"
-	expectEqual(t, fc, wantsDeploy, nil)
+	expectEqual(t, fc, wantsDeploy)
 
 	// Verify that when another actor sets ConfigMap data, it does not get
 	// overwritten by nameserver reconciler.
@@ -114,7 +114,7 @@ func TestNameserverReconciler(t *testing.T) {
 		TypeMeta: metav1.TypeMeta{Kind: "ConfigMap", APIVersion: "v1"},
 		Data:     map[string]string{"records.json": string(bs)},
 	}
-	expectEqual(t, fc, wantCm, nil)
+	expectEqual(t, fc, wantCm)
 
 	// Verify that if dnsconfig.spec.nameserver.image.{repo,tag} are unset,
 	// the nameserver image defaults to tailscale/k8s-nameserver:unstable.
@@ -123,5 +123,5 @@ func TestNameserverReconciler(t *testing.T) {
 	})
 	expectReconciled(t, nr, "", "test")
 	wantsDeploy.Spec.Template.Spec.Containers[0].Image = "tailscale/k8s-nameserver:unstable"
-	expectEqual(t, fc, wantsDeploy, nil)
+	expectEqual(t, fc, wantsDeploy)
 }

cmd/k8s-operator/operator.go

@@ -11,20 +11,23 @@ import (
 	"context"
 	"os"
 	"regexp"
+	"strconv"
 	"strings"
 	"time"
 
 	"github.com/go-logr/zapr"
 	"go.uber.org/zap"
 	"go.uber.org/zap/zapcore"
-	"golang.org/x/oauth2/clientcredentials"
 	appsv1 "k8s.io/api/apps/v1"
 	corev1 "k8s.io/api/core/v1"
 	discoveryv1 "k8s.io/api/discovery/v1"
 	networkingv1 "k8s.io/api/networking/v1"
 	rbacv1 "k8s.io/api/rbac/v1"
+	apiextensionsv1 "k8s.io/apiextensions-apiserver/pkg/apis/apiextensions/v1"
+	"k8s.io/apimachinery/pkg/fields"
 	"k8s.io/apimachinery/pkg/types"
 	"k8s.io/client-go/rest"
+	toolscache "k8s.io/client-go/tools/cache"
 	"sigs.k8s.io/controller-runtime/pkg/builder"
 	"sigs.k8s.io/controller-runtime/pkg/cache"
 	"sigs.k8s.io/controller-runtime/pkg/client"
@@ -84,6 +87,15 @@ func main() {
 	zlog := kzap.NewRaw(opts...).Sugar()
 	logf.SetLogger(zapr.NewLogger(zlog.Desugar()))
 
+	if tsNamespace == "" {
+		const namespaceFile = "/var/run/secrets/kubernetes.io/serviceaccount/namespace"
+		b, err := os.ReadFile(namespaceFile)
+		if err != nil {
+			zlog.Fatalf("Could not get operator namespace from OPERATOR_NAMESPACE environment variable or default projected volume: %v", err)
+		}
+		tsNamespace = strings.TrimSpace(string(b))
+	}
+
 	// The operator can run either as a plain operator or it can
 	// additionally act as api-server proxy
 	// https://tailscale.com/kb/1236/kubernetes-operator/?q=kubernetes#accessing-the-kubernetes-control-plane-using-an-api-server-proxy.
@@ -94,14 +106,14 @@ func main() {
 		hostinfo.SetApp(kubetypes.AppAPIServerProxy)
 	}
 
-	s, tsClient := initTSNet(zlog)
+	s, tsc := initTSNet(zlog)
 	defer s.Close()
 	restConfig := config.GetConfigOrDie()
 	maybeLaunchAPIServerProxy(zlog, restConfig, s, mode)
 	rOpts := reconcilerOpts{
 		log:                           zlog,
 		tsServer:                      s,
-		tsClient:                      tsClient,
+		tsClient:                      tsc,
 		tailscaleNamespace:            tsNamespace,
 		restConfig:                    restConfig,
 		proxyImage:                    image,
@@ -117,7 +129,7 @@ func main() {
 // initTSNet initializes the tsnet.Server and logs in to Tailscale. It uses the
 // CLIENT_ID_FILE and CLIENT_SECRET_FILE environment variables to authenticate
 // with Tailscale.
-func initTSNet(zlog *zap.SugaredLogger) (*tsnet.Server, *tailscale.Client) {
+func initTSNet(zlog *zap.SugaredLogger) (*tsnet.Server, tsClient) {
 	var (
 		clientIDPath     = defaultEnv("CLIENT_ID_FILE", "")
 		clientSecretPath = defaultEnv("CLIENT_SECRET_FILE", "")
@@ -129,27 +141,21 @@ func initTSNet(zlog *zap.SugaredLogger) (*tsnet.Server, *tailscale.Client) {
 	if clientIDPath == "" || clientSecretPath == "" {
 		startlog.Fatalf("CLIENT_ID_FILE and CLIENT_SECRET_FILE must be set")
 	}
-	clientID, err := os.ReadFile(clientIDPath)
+	tsc, err := newTSClient(context.Background(), clientIDPath, clientSecretPath)
 	if err != nil {
-		startlog.Fatalf("reading client ID %q: %v", clientIDPath, err)
+		startlog.Fatalf("error creating Tailscale client: %v", err)
 	}
-	clientSecret, err := os.ReadFile(clientSecretPath)
-	if err != nil {
-		startlog.Fatalf("reading client secret %q: %v", clientSecretPath, err)
-	}
-	credentials := clientcredentials.Config{
-		ClientID:     string(clientID),
-		ClientSecret: string(clientSecret),
-		TokenURL:     "https://login.tailscale.com/api/v2/oauth/token",
-	}
-	tsClient := tailscale.NewClient("-", nil)
-	tsClient.UserAgent = "tailscale-k8s-operator"
-	tsClient.HTTPClient = credentials.Client(context.Background())
-
 	s := &tsnet.Server{
 		Hostname: hostname,
 		Logf:     zlog.Named("tailscaled").Debugf,
 	}
+	if p := os.Getenv("TS_PORT"); p != "" {
+		port, err := strconv.ParseUint(p, 10, 16)
+		if err != nil {
+			startlog.Fatalf("TS_PORT %q cannot be parsed as uint16: %v", p, err)
+		}
+		s.Port = uint16(port)
+	}
 	if kubeSecret != "" {
 		st, err := kubestore.New(logger.Discard, kubeSecret)
 		if err != nil {
@@ -191,7 +197,7 @@ waitOnline:
 					},
 				},
 			}
-			authkey, _, err := tsClient.CreateKey(ctx, caps)
+			authkey, _, err := tsc.CreateKey(ctx, caps)
 			if err != nil {
 				startlog.Fatalf("creating operator authkey: %v", err)
 			}
@@ -215,7 +221,7 @@ waitOnline:
 		}
 		time.Sleep(time.Second)
 	}
-	return s, tsClient
+	return s, tsc
 }
 
 // runReconcilers starts the controller-runtime manager and registers the
@@ -231,21 +237,29 @@ func runReconcilers(opts reconcilerOpts) {
 	nsFilter := cache.ByObject{
 		Field: client.InNamespace(opts.tailscaleNamespace).AsSelector(),
 	}
+	// We watch the ServiceMonitor CRD to ensure that reconcilers are re-triggered if user's workflows result in the
+	// ServiceMonitor CRD applied after some of our resources that define ServiceMonitor creation. This selector
+	// ensures that we only watch the ServiceMonitor CRD and that we don't cache full contents of it.
+	serviceMonitorSelector := cache.ByObject{
+		Field:     fields.SelectorFromSet(fields.Set{"metadata.name": serviceMonitorCRD}),
+		Transform: crdTransformer(startlog),
+	}
 	mgrOpts := manager.Options{
 		// TODO (irbekrm): stricter filtering what we watch/cache/call
 		// reconcilers on. c/r by default starts a watch on any
 		// resources that we GET via the controller manager's client.
 		Cache: cache.Options{
 			ByObject: map[client.Object]cache.ByObject{
-				&corev1.Secret{}:             nsFilter,
-				&corev1.ServiceAccount{}:     nsFilter,
-				&corev1.Pod{}:                nsFilter,
-				&corev1.ConfigMap{}:          nsFilter,
-				&appsv1.StatefulSet{}:        nsFilter,
-				&appsv1.Deployment{}:         nsFilter,
-				&discoveryv1.EndpointSlice{}: nsFilter,
-				&rbacv1.Role{}:               nsFilter,
-				&rbacv1.RoleBinding{}:        nsFilter,
+				&corev1.Secret{}:                            nsFilter,
+				&corev1.ServiceAccount{}:                    nsFilter,
+				&corev1.Pod{}:                               nsFilter,
+				&corev1.ConfigMap{}:                         nsFilter,
+				&appsv1.StatefulSet{}:                       nsFilter,
+				&appsv1.Deployment{}:                        nsFilter,
+				&discoveryv1.EndpointSlice{}:                nsFilter,
+				&rbacv1.Role{}:                              nsFilter,
+				&rbacv1.RoleBinding{}:                       nsFilter,
+				&apiextensionsv1.CustomResourceDefinition{}: serviceMonitorSelector,
 			},
 		},
 		Scheme: tsapi.GlobalScheme,
@@ -301,6 +315,7 @@ func runReconcilers(opts reconcilerOpts) {
 	err = builder.
 		ControllerManagedBy(mgr).
 		For(&networkingv1.Ingress{}).
+		Named("ingress-reconciler").
 		Watches(&appsv1.StatefulSet{}, ingressChildFilter).
 		Watches(&corev1.Secret{}, ingressChildFilter).
 		Watches(&corev1.Service{}, svcHandlerForIngress).
@@ -315,6 +330,28 @@ func runReconcilers(opts reconcilerOpts) {
 	if err != nil {
 		startlog.Fatalf("could not create ingress reconciler: %v", err)
 	}
+	lc, err := opts.tsServer.LocalClient()
+	if err != nil {
+		startlog.Fatalf("could not get local client: %v", err)
+	}
+	err = builder.
+		ControllerManagedBy(mgr).
+		For(&networkingv1.Ingress{}).
+		Named("ingress-pg-reconciler").
+		Watches(&corev1.Service{}, handler.EnqueueRequestsFromMapFunc(serviceHandlerForIngressPG(mgr.GetClient(), startlog))).
+		Complete(&IngressPGReconciler{
+			recorder:    eventRecorder,
+			tsClient:    opts.tsClient,
+			tsnetServer: opts.tsServer,
+			defaultTags: strings.Split(opts.proxyTags, ","),
+			Client:      mgr.GetClient(),
+			logger:      opts.log.Named("ingress-pg-reconciler"),
+			lc:          lc,
+			tsNamespace: opts.tailscaleNamespace,
+		})
+	if err != nil {
+		startlog.Fatalf("could not create ingress-pg-reconciler: %v", err)
+	}
 
 	connectorFilter := handler.EnqueueRequestsFromMapFunc(managedResourceHandlerForType("connector"))
 	// If a ProxyClassChanges, enqueue all Connectors that have
@@ -322,6 +359,7 @@ func runReconcilers(opts reconcilerOpts) {
 	proxyClassFilterForConnector := handler.EnqueueRequestsFromMapFunc(proxyClassHandlerForConnector(mgr.GetClient(), startlog))
 	err = builder.ControllerManagedBy(mgr).
 		For(&tsapi.Connector{}).
+		Named("connector-reconciler").
 		Watches(&appsv1.StatefulSet{}, connectorFilter).
 		Watches(&corev1.Secret{}, connectorFilter).
 		Watches(&tsapi.ProxyClass{}, proxyClassFilterForConnector).
@@ -341,6 +379,7 @@ func runReconcilers(opts reconcilerOpts) {
 	nameserverFilter := handler.EnqueueRequestsFromMapFunc(managedResourceHandlerForType("nameserver"))
 	err = builder.ControllerManagedBy(mgr).
 		For(&tsapi.DNSConfig{}).
+		Named("nameserver-reconciler").
 		Watches(&appsv1.Deployment{}, nameserverFilter).
 		Watches(&corev1.ConfigMap{}, nameserverFilter).
 		Watches(&corev1.Service{}, nameserverFilter).
@@ -414,8 +453,14 @@ func runReconcilers(opts reconcilerOpts) {
 		startlog.Fatalf("could not create egress EndpointSlices reconciler: %v", err)
 	}
 
+	// ProxyClass reconciler gets triggered on ServiceMonitor CRD changes to ensure that any ProxyClasses, that
+	// define that a ServiceMonitor should be created, were set to invalid because the CRD did not exist get
+	// reconciled if the CRD is applied at a later point.
+	serviceMonitorFilter := handler.EnqueueRequestsFromMapFunc(proxyClassesWithServiceMonitor(mgr.GetClient(), opts.log))
 	err = builder.ControllerManagedBy(mgr).
 		For(&tsapi.ProxyClass{}).
+		Named("proxyclass-reconciler").
+		Watches(&apiextensionsv1.CustomResourceDefinition{}, serviceMonitorFilter).
 		Complete(&ProxyClassReconciler{
 			Client:   mgr.GetClient(),
 			recorder: eventRecorder,
@@ -458,6 +503,7 @@ func runReconcilers(opts reconcilerOpts) {
 	recorderFilter := handler.EnqueueRequestForOwner(mgr.GetScheme(), mgr.GetRESTMapper(), &tsapi.Recorder{})
 	err = builder.ControllerManagedBy(mgr).
 		For(&tsapi.Recorder{}).
+		Named("recorder-reconciler").
 		Watches(&appsv1.StatefulSet{}, recorderFilter).
 		Watches(&corev1.ServiceAccount{}, recorderFilter).
 		Watches(&corev1.Secret{}, recorderFilter).
@@ -475,12 +521,14 @@ func runReconcilers(opts reconcilerOpts) {
 		startlog.Fatalf("could not create Recorder reconciler: %v", err)
 	}
 
-	// Recorder reconciler.
+	// ProxyGroup reconciler.
 	ownedByProxyGroupFilter := handler.EnqueueRequestForOwner(mgr.GetScheme(), mgr.GetRESTMapper(), &tsapi.ProxyGroup{})
 	proxyClassFilterForProxyGroup := handler.EnqueueRequestsFromMapFunc(proxyClassHandlerForProxyGroup(mgr.GetClient(), startlog))
 	err = builder.ControllerManagedBy(mgr).
 		For(&tsapi.ProxyGroup{}).
+		Named("proxygroup-reconciler").
 		Watches(&appsv1.StatefulSet{}, ownedByProxyGroupFilter).
+		Watches(&corev1.ConfigMap{}, ownedByProxyGroupFilter).
 		Watches(&corev1.ServiceAccount{}, ownedByProxyGroupFilter).
 		Watches(&corev1.Secret{}, ownedByProxyGroupFilter).
 		Watches(&rbacv1.Role{}, ownedByProxyGroupFilter).
@@ -512,7 +560,7 @@ func runReconcilers(opts reconcilerOpts) {
 type reconcilerOpts struct {
 	log                *zap.SugaredLogger
 	tsServer           *tsnet.Server
-	tsClient           *tailscale.Client
+	tsClient           tsClient
 	tailscaleNamespace string       // namespace in which operator resources will be deployed
 	restConfig         *rest.Config // config for connecting to the kube API server
 	proxyImage         string       // <proxy-image-repo>:<proxy-image-tag>
@@ -637,12 +685,6 @@ func dnsRecordsReconcilerIngressHandler(ns string, isDefaultLoadBalancer bool, c
 	}
 }
 
-type tsClient interface {
-	CreateKey(ctx context.Context, caps tailscale.KeyCapabilities) (string, *tailscale.Key, error)
-	Device(ctx context.Context, deviceID string, fields *tailscale.DeviceFieldsOpts) (*tailscale.Device, error)
-	DeleteDevice(ctx context.Context, nodeStableID string) error
-}
-
 func isManagedResource(o client.Object) bool {
 	ls := o.GetLabels()
 	return ls[LabelManaged] == "true"
@@ -778,6 +820,10 @@ func serviceHandlerForIngress(cl client.Client, logger *zap.SugaredLogger) handl
 			if ing.Spec.IngressClassName == nil || *ing.Spec.IngressClassName != tailscaleIngressClassName {
 				return nil
 			}
+			if hasProxyGroupAnnotation(&ing) {
+				// We don't want to reconcile backend Services for Ingresses for ProxyGroups.
+				continue
+			}
 			if ing.Spec.DefaultBackend != nil && ing.Spec.DefaultBackend.Service != nil && ing.Spec.DefaultBackend.Service.Name == o.GetName() {
 				reqs = append(reqs, reconcile.Request{NamespacedName: client.ObjectKeyFromObject(&ing)})
 			}
@@ -1010,6 +1056,49 @@ func epsFromExternalNameService(cl client.Client, logger *zap.SugaredLogger, ns
 	}
 }
 
+// proxyClassesWithServiceMonitor returns an event handler that, given that the event is for the Prometheus
+// ServiceMonitor CRD, returns all ProxyClasses that define that a ServiceMonitor should be created.
+func proxyClassesWithServiceMonitor(cl client.Client, logger *zap.SugaredLogger) handler.MapFunc {
+	return func(ctx context.Context, o client.Object) []reconcile.Request {
+		crd, ok := o.(*apiextensionsv1.CustomResourceDefinition)
+		if !ok {
+			logger.Debugf("[unexpected] ServiceMonitor CRD handler received an object that is not a CustomResourceDefinition")
+			return nil
+		}
+		if crd.Name != serviceMonitorCRD {
+			logger.Debugf("[unexpected] ServiceMonitor CRD handler received an unexpected CRD %q", crd.Name)
+			return nil
+		}
+		pcl := &tsapi.ProxyClassList{}
+		if err := cl.List(ctx, pcl); err != nil {
+			logger.Debugf("[unexpected] error listing ProxyClasses: %v", err)
+			return nil
+		}
+		reqs := make([]reconcile.Request, 0)
+		for _, pc := range pcl.Items {
+			if pc.Spec.Metrics != nil && pc.Spec.Metrics.ServiceMonitor != nil && pc.Spec.Metrics.ServiceMonitor.Enable {
+				reqs = append(reqs, reconcile.Request{
+					NamespacedName: types.NamespacedName{Namespace: pc.Namespace, Name: pc.Name},
+				})
+			}
+		}
+		return reqs
+	}
+}
+
+// crdTransformer gets called before a CRD is stored to c/r cache, it removes the CRD spec to reduce memory consumption.
+func crdTransformer(log *zap.SugaredLogger) toolscache.TransformFunc {
+	return func(o any) (any, error) {
+		crd, ok := o.(*apiextensionsv1.CustomResourceDefinition)
+		if !ok {
+			log.Infof("[unexpected] CRD transformer called for a non-CRD type")
+			return crd, nil
+		}
+		crd.Spec = apiextensionsv1.CustomResourceDefinitionSpec{}
+		return crd, nil
+	}
+}
+
 // indexEgressServices adds a local index to a cached Tailscale egress Services meant to be exposed on a ProxyGroup. The
 // index is used a list filter.
 func indexEgressServices(o client.Object) []string {
@@ -1018,3 +1107,44 @@ func indexEgressServices(o client.Object) []string {
 	}
 	return []string{o.GetAnnotations()[AnnotationProxyGroup]}
 }
+
+// serviceHandlerForIngressPG returns a handler for Service events that ensures that if the Service
+// associated with an event is a backend Service for a tailscale Ingress with ProxyGroup annotation,
+// the associated Ingress gets reconciled.
+func serviceHandlerForIngressPG(cl client.Client, logger *zap.SugaredLogger) handler.MapFunc {
+	return func(ctx context.Context, o client.Object) []reconcile.Request {
+		ingList := networkingv1.IngressList{}
+		if err := cl.List(ctx, &ingList, client.InNamespace(o.GetNamespace())); err != nil {
+			logger.Debugf("error listing Ingresses: %v", err)
+			return nil
+		}
+		reqs := make([]reconcile.Request, 0)
+		for _, ing := range ingList.Items {
+			if ing.Spec.IngressClassName == nil || *ing.Spec.IngressClassName != tailscaleIngressClassName {
+				continue
+			}
+			if !hasProxyGroupAnnotation(&ing) {
+				continue
+			}
+			if ing.Spec.DefaultBackend != nil && ing.Spec.DefaultBackend.Service != nil && ing.Spec.DefaultBackend.Service.Name == o.GetName() {
+				reqs = append(reqs, reconcile.Request{NamespacedName: client.ObjectKeyFromObject(&ing)})
+			}
+			for _, rule := range ing.Spec.Rules {
+				if rule.HTTP == nil {
+					continue
+				}
+				for _, path := range rule.HTTP.Paths {
+					if path.Backend.Service != nil && path.Backend.Service.Name == o.GetName() {
+						reqs = append(reqs, reconcile.Request{NamespacedName: client.ObjectKeyFromObject(&ing)})
+					}
+				}
+			}
+		}
+		return reqs
+	}
+}
+
+func hasProxyGroupAnnotation(obj client.Object) bool {
+	ing := obj.(*networkingv1.Ingress)
+	return ing.Annotations[AnnotationProxyGroup] != ""
+}

cmd/k8s-operator/operator_test.go

@@ -16,6 +16,7 @@ import (
 	appsv1 "k8s.io/api/apps/v1"
 	corev1 "k8s.io/api/core/v1"
 	networkingv1 "k8s.io/api/networking/v1"
+	apiextensionsv1 "k8s.io/apiextensions-apiserver/pkg/apis/apiextensions/v1"
 	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
 	"k8s.io/apimachinery/pkg/types"
 	"k8s.io/client-go/tools/record"
@@ -105,7 +106,7 @@ func TestLoadBalancerClass(t *testing.T) {
 			}},
 		},
 	}
-	expectEqual(t, fc, want, nil)
+	expectEqual(t, fc, want)
 
 	// Delete the misconfiguration so the proxy starts getting created on the
 	// next reconcile.
@@ -127,9 +128,9 @@ func TestLoadBalancerClass(t *testing.T) {
 		app:             kubetypes.AppIngressProxy,
 	}
 
-	expectEqual(t, fc, expectedSecret(t, fc, opts), nil)
-	expectEqual(t, fc, expectedHeadlessService(shortName, "svc"), nil)
-	expectEqual(t, fc, expectedSTS(t, fc, opts), removeHashAnnotation)
+	expectEqual(t, fc, expectedSecret(t, fc, opts))
+	expectEqual(t, fc, expectedHeadlessService(shortName, "svc"))
+	expectEqual(t, fc, expectedSTS(t, fc, opts), removeHashAnnotation, removeResourceReqs)
 
 	want.Annotations = nil
 	want.ObjectMeta.Finalizers = []string{"tailscale.com/finalizer"}
@@ -142,7 +143,7 @@ func TestLoadBalancerClass(t *testing.T) {
 			Message:            "no Tailscale hostname known yet, waiting for proxy pod to finish auth",
 		}},
 	}
-	expectEqual(t, fc, want, nil)
+	expectEqual(t, fc, want)
 
 	// Normally the Tailscale proxy pod would come up here and write its info
 	// into the secret. Simulate that, then verify reconcile again and verify
@@ -168,7 +169,7 @@ func TestLoadBalancerClass(t *testing.T) {
 			},
 		},
 	}
-	expectEqual(t, fc, want, nil)
+	expectEqual(t, fc, want)
 
 	// Turn the service back into a ClusterIP service, which should make the
 	// operator clean up.
@@ -205,7 +206,7 @@ func TestLoadBalancerClass(t *testing.T) {
 			Type:      corev1.ServiceTypeClusterIP,
 		},
 	}
-	expectEqual(t, fc, want, nil)
+	expectEqual(t, fc, want)
 }
 
 func TestTailnetTargetFQDNAnnotation(t *testing.T) {
@@ -265,9 +266,9 @@ func TestTailnetTargetFQDNAnnotation(t *testing.T) {
 		app:               kubetypes.AppEgressProxy,
 	}
 
-	expectEqual(t, fc, expectedSecret(t, fc, o), nil)
-	expectEqual(t, fc, expectedHeadlessService(shortName, "svc"), nil)
-	expectEqual(t, fc, expectedSTS(t, fc, o), removeHashAnnotation)
+	expectEqual(t, fc, expectedSecret(t, fc, o))
+	expectEqual(t, fc, expectedHeadlessService(shortName, "svc"))
+	expectEqual(t, fc, expectedSTS(t, fc, o), removeHashAnnotation, removeResourceReqs)
 	want := &corev1.Service{
 		ObjectMeta: metav1.ObjectMeta{
 			Name:       "test",
@@ -287,10 +288,10 @@ func TestTailnetTargetFQDNAnnotation(t *testing.T) {
 			Conditions: proxyCreatedCondition(clock),
 		},
 	}
-	expectEqual(t, fc, want, nil)
-	expectEqual(t, fc, expectedSecret(t, fc, o), nil)
-	expectEqual(t, fc, expectedHeadlessService(shortName, "svc"), nil)
-	expectEqual(t, fc, expectedSTS(t, fc, o), removeHashAnnotation)
+	expectEqual(t, fc, want)
+	expectEqual(t, fc, expectedSecret(t, fc, o))
+	expectEqual(t, fc, expectedHeadlessService(shortName, "svc"))
+	expectEqual(t, fc, expectedSTS(t, fc, o), removeHashAnnotation, removeResourceReqs)
 
 	// Change the tailscale-target-fqdn annotation which should update the
 	// StatefulSet
@@ -377,9 +378,9 @@ func TestTailnetTargetIPAnnotation(t *testing.T) {
 		app:             kubetypes.AppEgressProxy,
 	}
 
-	expectEqual(t, fc, expectedSecret(t, fc, o), nil)
-	expectEqual(t, fc, expectedHeadlessService(shortName, "svc"), nil)
-	expectEqual(t, fc, expectedSTS(t, fc, o), removeHashAnnotation)
+	expectEqual(t, fc, expectedSecret(t, fc, o))
+	expectEqual(t, fc, expectedHeadlessService(shortName, "svc"))
+	expectEqual(t, fc, expectedSTS(t, fc, o), removeHashAnnotation, removeResourceReqs)
 	want := &corev1.Service{
 		ObjectMeta: metav1.ObjectMeta{
 			Name:       "test",
@@ -399,10 +400,10 @@ func TestTailnetTargetIPAnnotation(t *testing.T) {
 			Conditions: proxyCreatedCondition(clock),
 		},
 	}
-	expectEqual(t, fc, want, nil)
-	expectEqual(t, fc, expectedSecret(t, fc, o), nil)
-	expectEqual(t, fc, expectedHeadlessService(shortName, "svc"), nil)
-	expectEqual(t, fc, expectedSTS(t, fc, o), removeHashAnnotation)
+	expectEqual(t, fc, want)
+	expectEqual(t, fc, expectedSecret(t, fc, o))
+	expectEqual(t, fc, expectedHeadlessService(shortName, "svc"))
+	expectEqual(t, fc, expectedSTS(t, fc, o), removeHashAnnotation, removeResourceReqs)
 
 	// Change the tailscale-target-ip annotation which should update the
 	// StatefulSet
@@ -500,7 +501,7 @@ func TestTailnetTargetIPAnnotation_IPCouldNotBeParsed(t *testing.T) {
 		},
 	}
 
-	expectEqual(t, fc, want, nil)
+	expectEqual(t, fc, want)
 }
 
 func TestTailnetTargetIPAnnotation_InvalidIP(t *testing.T) {
@@ -571,7 +572,7 @@ func TestTailnetTargetIPAnnotation_InvalidIP(t *testing.T) {
 		},
 	}
 
-	expectEqual(t, fc, want, nil)
+	expectEqual(t, fc, want)
 }
 
 func TestAnnotations(t *testing.T) {
@@ -628,9 +629,9 @@ func TestAnnotations(t *testing.T) {
 		app:             kubetypes.AppIngressProxy,
 	}
 
-	expectEqual(t, fc, expectedSecret(t, fc, o), nil)
-	expectEqual(t, fc, expectedHeadlessService(shortName, "svc"), nil)
-	expectEqual(t, fc, expectedSTS(t, fc, o), removeHashAnnotation)
+	expectEqual(t, fc, expectedSecret(t, fc, o))
+	expectEqual(t, fc, expectedHeadlessService(shortName, "svc"))
+	expectEqual(t, fc, expectedSTS(t, fc, o), removeHashAnnotation, removeResourceReqs)
 	want := &corev1.Service{
 		ObjectMeta: metav1.ObjectMeta{
 			Name:       "test",
@@ -649,7 +650,7 @@ func TestAnnotations(t *testing.T) {
 			Conditions: proxyCreatedCondition(clock),
 		},
 	}
-	expectEqual(t, fc, want, nil)
+	expectEqual(t, fc, want)
 
 	// Turn the service back into a ClusterIP service, which should make the
 	// operator clean up.
@@ -677,7 +678,7 @@ func TestAnnotations(t *testing.T) {
 			Type:      corev1.ServiceTypeClusterIP,
 		},
 	}
-	expectEqual(t, fc, want, nil)
+	expectEqual(t, fc, want)
 }
 
 func TestAnnotationIntoLB(t *testing.T) {
@@ -734,9 +735,9 @@ func TestAnnotationIntoLB(t *testing.T) {
 		app:             kubetypes.AppIngressProxy,
 	}
 
-	expectEqual(t, fc, expectedSecret(t, fc, o), nil)
-	expectEqual(t, fc, expectedHeadlessService(shortName, "svc"), nil)
-	expectEqual(t, fc, expectedSTS(t, fc, o), removeHashAnnotation)
+	expectEqual(t, fc, expectedSecret(t, fc, o))
+	expectEqual(t, fc, expectedHeadlessService(shortName, "svc"))
+	expectEqual(t, fc, expectedSTS(t, fc, o), removeHashAnnotation, removeResourceReqs)
 
 	// Normally the Tailscale proxy pod would come up here and write its info
 	// into the secret. Simulate that, since it would have normally happened at
@@ -768,7 +769,7 @@ func TestAnnotationIntoLB(t *testing.T) {
 			Conditions: proxyCreatedCondition(clock),
 		},
 	}
-	expectEqual(t, fc, want, nil)
+	expectEqual(t, fc, want)
 
 	// Remove Tailscale's annotation, and at the same time convert the service
 	// into a tailscale LoadBalancer.
@@ -779,8 +780,8 @@ func TestAnnotationIntoLB(t *testing.T) {
 	})
 	expectReconciled(t, sr, "default", "test")
 	// None of the proxy machinery should have changed...
-	expectEqual(t, fc, expectedHeadlessService(shortName, "svc"), nil)
-	expectEqual(t, fc, expectedSTS(t, fc, o), removeHashAnnotation)
+	expectEqual(t, fc, expectedHeadlessService(shortName, "svc"))
+	expectEqual(t, fc, expectedSTS(t, fc, o), removeHashAnnotation, removeResourceReqs)
 	// ... but the service should have a LoadBalancer status.
 
 	want = &corev1.Service{
@@ -809,7 +810,7 @@ func TestAnnotationIntoLB(t *testing.T) {
 			Conditions: proxyCreatedCondition(clock),
 		},
 	}
-	expectEqual(t, fc, want, nil)
+	expectEqual(t, fc, want)
 }
 
 func TestLBIntoAnnotation(t *testing.T) {
@@ -864,9 +865,9 @@ func TestLBIntoAnnotation(t *testing.T) {
 		app:             kubetypes.AppIngressProxy,
 	}
 
-	expectEqual(t, fc, expectedSecret(t, fc, o), nil)
-	expectEqual(t, fc, expectedHeadlessService(shortName, "svc"), nil)
-	expectEqual(t, fc, expectedSTS(t, fc, o), removeHashAnnotation)
+	expectEqual(t, fc, expectedSecret(t, fc, o))
+	expectEqual(t, fc, expectedHeadlessService(shortName, "svc"))
+	expectEqual(t, fc, expectedSTS(t, fc, o), removeHashAnnotation, removeResourceReqs)
 
 	// Normally the Tailscale proxy pod would come up here and write its info
 	// into the secret. Simulate that, then verify reconcile again and verify
@@ -906,7 +907,7 @@ func TestLBIntoAnnotation(t *testing.T) {
 			Conditions: proxyCreatedCondition(clock),
 		},
 	}
-	expectEqual(t, fc, want, nil)
+	expectEqual(t, fc, want)
 
 	// Turn the service back into a ClusterIP service, but also add the
 	// tailscale annotation.
@@ -925,8 +926,8 @@ func TestLBIntoAnnotation(t *testing.T) {
 	})
 	expectReconciled(t, sr, "default", "test")
 
-	expectEqual(t, fc, expectedHeadlessService(shortName, "svc"), nil)
-	expectEqual(t, fc, expectedSTS(t, fc, o), removeHashAnnotation)
+	expectEqual(t, fc, expectedHeadlessService(shortName, "svc"))
+	expectEqual(t, fc, expectedSTS(t, fc, o), removeHashAnnotation, removeResourceReqs)
 
 	want = &corev1.Service{
 		ObjectMeta: metav1.ObjectMeta{
@@ -946,7 +947,7 @@ func TestLBIntoAnnotation(t *testing.T) {
 			Conditions: proxyCreatedCondition(clock),
 		},
 	}
-	expectEqual(t, fc, want, nil)
+	expectEqual(t, fc, want)
 }
 
 func TestCustomHostname(t *testing.T) {
@@ -1004,9 +1005,9 @@ func TestCustomHostname(t *testing.T) {
 		app:             kubetypes.AppIngressProxy,
 	}
 
-	expectEqual(t, fc, expectedSecret(t, fc, o), nil)
-	expectEqual(t, fc, expectedHeadlessService(shortName, "svc"), nil)
-	expectEqual(t, fc, expectedSTS(t, fc, o), removeHashAnnotation)
+	expectEqual(t, fc, expectedSecret(t, fc, o))
+	expectEqual(t, fc, expectedHeadlessService(shortName, "svc"))
+	expectEqual(t, fc, expectedSTS(t, fc, o), removeHashAnnotation, removeResourceReqs)
 	want := &corev1.Service{
 		ObjectMeta: metav1.ObjectMeta{
 			Name:       "test",
@@ -1026,7 +1027,7 @@ func TestCustomHostname(t *testing.T) {
 			Conditions: proxyCreatedCondition(clock),
 		},
 	}
-	expectEqual(t, fc, want, nil)
+	expectEqual(t, fc, want)
 
 	// Turn the service back into a ClusterIP service, which should make the
 	// operator clean up.
@@ -1057,7 +1058,7 @@ func TestCustomHostname(t *testing.T) {
 			Type:      corev1.ServiceTypeClusterIP,
 		},
 	}
-	expectEqual(t, fc, want, nil)
+	expectEqual(t, fc, want)
 }
 
 func TestCustomPriorityClassName(t *testing.T) {
@@ -1117,7 +1118,7 @@ func TestCustomPriorityClassName(t *testing.T) {
 		app:               kubetypes.AppIngressProxy,
 	}
 
-	expectEqual(t, fc, expectedSTS(t, fc, o), removeHashAnnotation)
+	expectEqual(t, fc, expectedSTS(t, fc, o), removeHashAnnotation, removeResourceReqs)
 }
 
 func TestProxyClassForService(t *testing.T) {
@@ -1129,7 +1130,7 @@ func TestProxyClassForService(t *testing.T) {
 				AcceptRoutes: true,
 			},
 			StatefulSet: &tsapi.StatefulSet{
-				Labels:      map[string]string{"foo": "bar"},
+				Labels:      tsapi.Labels{"foo": "bar"},
 				Annotations: map[string]string{"bar.io/foo": "some-val"},
 				Pod:         &tsapi.Pod{Annotations: map[string]string{"foo.io/bar": "some-val"}}}},
 	}
@@ -1185,9 +1186,9 @@ func TestProxyClassForService(t *testing.T) {
 		clusterTargetIP: "10.20.30.40",
 		app:             kubetypes.AppIngressProxy,
 	}
-	expectEqual(t, fc, expectedSecret(t, fc, opts), nil)
-	expectEqual(t, fc, expectedHeadlessService(shortName, "svc"), nil)
-	expectEqual(t, fc, expectedSTS(t, fc, opts), removeHashAnnotation)
+	expectEqual(t, fc, expectedSecret(t, fc, opts))
+	expectEqual(t, fc, expectedHeadlessService(shortName, "svc"))
+	expectEqual(t, fc, expectedSTS(t, fc, opts), removeHashAnnotation, removeResourceReqs)
 
 	// 2. The Service gets updated with tailscale.com/proxy-class label
 	// pointing at the 'custom-metadata' ProxyClass. The ProxyClass is not
@@ -1196,8 +1197,8 @@ func TestProxyClassForService(t *testing.T) {
 		mak.Set(&svc.Labels, LabelProxyClass, "custom-metadata")
 	})
 	expectReconciled(t, sr, "default", "test")
-	expectEqual(t, fc, expectedSTS(t, fc, opts), removeHashAnnotation)
-	expectEqual(t, fc, expectedSecret(t, fc, opts), nil)
+	expectEqual(t, fc, expectedSTS(t, fc, opts), removeHashAnnotation, removeResourceReqs)
+	expectEqual(t, fc, expectedSecret(t, fc, opts))
 
 	// 3. ProxyClass is set to Ready, the Service gets reconciled by the
 	// services-reconciler and the customization from the ProxyClass is
@@ -1212,7 +1213,7 @@ func TestProxyClassForService(t *testing.T) {
 	})
 	opts.proxyClass = pc.Name
 	expectReconciled(t, sr, "default", "test")
-	expectEqual(t, fc, expectedSTS(t, fc, opts), removeHashAnnotation)
+	expectEqual(t, fc, expectedSTS(t, fc, opts), removeHashAnnotation, removeResourceReqs)
 	expectEqual(t, fc, expectedSecret(t, fc, opts), removeAuthKeyIfExistsModifier(t))
 
 	// 4. tailscale.com/proxy-class label is removed from the Service, the
@@ -1223,7 +1224,7 @@ func TestProxyClassForService(t *testing.T) {
 	})
 	opts.proxyClass = ""
 	expectReconciled(t, sr, "default", "test")
-	expectEqual(t, fc, expectedSTS(t, fc, opts), removeHashAnnotation)
+	expectEqual(t, fc, expectedSTS(t, fc, opts), removeHashAnnotation, removeResourceReqs)
 }
 
 func TestDefaultLoadBalancer(t *testing.T) {
@@ -1269,7 +1270,7 @@ func TestDefaultLoadBalancer(t *testing.T) {
 
 	fullName, shortName := findGenName(t, fc, "default", "test", "svc")
 
-	expectEqual(t, fc, expectedHeadlessService(shortName, "svc"), nil)
+	expectEqual(t, fc, expectedHeadlessService(shortName, "svc"))
 	o := configOpts{
 		stsName:         shortName,
 		secretName:      fullName,
@@ -1279,8 +1280,7 @@ func TestDefaultLoadBalancer(t *testing.T) {
 		clusterTargetIP: "10.20.30.40",
 		app:             kubetypes.AppIngressProxy,
 	}
-	expectEqual(t, fc, expectedSTS(t, fc, o), removeHashAnnotation)
-
+	expectEqual(t, fc, expectedSTS(t, fc, o), removeHashAnnotation, removeResourceReqs)
 }
 
 func TestProxyFirewallMode(t *testing.T) {
@@ -1336,7 +1336,7 @@ func TestProxyFirewallMode(t *testing.T) {
 		clusterTargetIP: "10.20.30.40",
 		app:             kubetypes.AppIngressProxy,
 	}
-	expectEqual(t, fc, expectedSTS(t, fc, o), removeHashAnnotation)
+	expectEqual(t, fc, expectedSTS(t, fc, o), removeHashAnnotation, removeResourceReqs)
 }
 
 func TestTailscaledConfigfileHash(t *testing.T) {
@@ -1378,6 +1378,7 @@ func TestTailscaledConfigfileHash(t *testing.T) {
 		},
 	})
 
+	expectReconciled(t, sr, "default", "test")
 	expectReconciled(t, sr, "default", "test")
 
 	fullName, shortName := findGenName(t, fc, "default", "test", "svc")
@@ -1388,10 +1389,10 @@ func TestTailscaledConfigfileHash(t *testing.T) {
 		parentType:      "svc",
 		hostname:        "default-test",
 		clusterTargetIP: "10.20.30.40",
-		confFileHash:    "e09bededa0379920141cbd0b0dbdf9b8b66545877f9e8397423f5ce3e1ba439e",
+		confFileHash:    "848bff4b5ba83ac999e6984c8464e597156daba961ae045e7dbaef606d54ab5e",
 		app:             kubetypes.AppIngressProxy,
 	}
-	expectEqual(t, fc, expectedSTS(t, fc, o), nil)
+	expectEqual(t, fc, expectedSTS(t, fc, o), removeResourceReqs)
 
 	// 2. Hostname gets changed, configfile is updated and a new hash value
 	// is produced.
@@ -1399,9 +1400,9 @@ func TestTailscaledConfigfileHash(t *testing.T) {
 		mak.Set(&svc.Annotations, AnnotationHostname, "another-test")
 	})
 	o.hostname = "another-test"
-	o.confFileHash = "5d754cf55463135ee34aa9821f2fd8483b53eb0570c3740c84a086304f427684"
+	o.confFileHash = "d4cc13f09f55f4f6775689004f9a466723325b84d2b590692796bfe22aeaa389"
 	expectReconciled(t, sr, "default", "test")
-	expectEqual(t, fc, expectedSTS(t, fc, o), nil)
+	expectEqual(t, fc, expectedSTS(t, fc, o), removeResourceReqs)
 }
 func Test_isMagicDNSName(t *testing.T) {
 	tests := []struct {
@@ -1679,9 +1680,9 @@ func Test_authKeyRemoval(t *testing.T) {
 		app:             kubetypes.AppIngressProxy,
 	}
 
-	expectEqual(t, fc, expectedSecret(t, fc, opts), nil)
-	expectEqual(t, fc, expectedHeadlessService(shortName, "svc"), nil)
-	expectEqual(t, fc, expectedSTS(t, fc, opts), removeHashAnnotation)
+	expectEqual(t, fc, expectedSecret(t, fc, opts))
+	expectEqual(t, fc, expectedHeadlessService(shortName, "svc"))
+	expectEqual(t, fc, expectedSTS(t, fc, opts), removeHashAnnotation, removeResourceReqs)
 
 	// 2. Apply update to the Secret that imitates the proxy setting device_id.
 	s := expectedSecret(t, fc, opts)
@@ -1693,7 +1694,7 @@ func Test_authKeyRemoval(t *testing.T) {
 	expectReconciled(t, sr, "default", "test")
 	opts.shouldRemoveAuthKey = true
 	opts.secretExtraData = map[string][]byte{"device_id": []byte("dkkdi4CNTRL")}
-	expectEqual(t, fc, expectedSecret(t, fc, opts), nil)
+	expectEqual(t, fc, expectedSecret(t, fc, opts))
 }
 
 func Test_externalNameService(t *testing.T) {
@@ -1753,9 +1754,9 @@ func Test_externalNameService(t *testing.T) {
 		app:              kubetypes.AppIngressProxy,
 	}
 
-	expectEqual(t, fc, expectedSecret(t, fc, opts), nil)
-	expectEqual(t, fc, expectedHeadlessService(shortName, "svc"), nil)
-	expectEqual(t, fc, expectedSTS(t, fc, opts), removeHashAnnotation)
+	expectEqual(t, fc, expectedSecret(t, fc, opts))
+	expectEqual(t, fc, expectedHeadlessService(shortName, "svc"))
+	expectEqual(t, fc, expectedSTS(t, fc, opts), removeHashAnnotation, removeResourceReqs)
 
 	// 2. Change the ExternalName and verify that changes get propagated.
 	mustUpdate(t, sr, "default", "test", func(s *corev1.Service) {
@@ -1763,7 +1764,107 @@ func Test_externalNameService(t *testing.T) {
 	})
 	expectReconciled(t, sr, "default", "test")
 	opts.clusterTargetDNS = "bar.com"
-	expectEqual(t, fc, expectedSTS(t, fc, opts), removeHashAnnotation)
+	expectEqual(t, fc, expectedSTS(t, fc, opts), removeHashAnnotation, removeResourceReqs)
+}
+
+func Test_metricsResourceCreation(t *testing.T) {
+	pc := &tsapi.ProxyClass{
+		ObjectMeta: metav1.ObjectMeta{Name: "metrics", Generation: 1},
+		Spec:       tsapi.ProxyClassSpec{},
+		Status: tsapi.ProxyClassStatus{
+			Conditions: []metav1.Condition{{
+				Status:             metav1.ConditionTrue,
+				Type:               string(tsapi.ProxyClassReady),
+				ObservedGeneration: 1,
+			}}},
+	}
+	svc := &corev1.Service{
+		ObjectMeta: metav1.ObjectMeta{
+			Name:      "test",
+			Namespace: "default",
+			UID:       types.UID("1234-UID"),
+			Labels:    map[string]string{LabelProxyClass: "metrics"},
+		},
+		Spec: corev1.ServiceSpec{
+			ClusterIP:         "10.20.30.40",
+			Type:              corev1.ServiceTypeLoadBalancer,
+			LoadBalancerClass: ptr.To("tailscale"),
+		},
+	}
+	crd := &apiextensionsv1.CustomResourceDefinition{ObjectMeta: metav1.ObjectMeta{Name: serviceMonitorCRD}}
+	fc := fake.NewClientBuilder().
+		WithScheme(tsapi.GlobalScheme).
+		WithObjects(pc, svc).
+		WithStatusSubresource(pc).
+		Build()
+	ft := &fakeTSClient{}
+	zl, err := zap.NewDevelopment()
+	if err != nil {
+		t.Fatal(err)
+	}
+	clock := tstest.NewClock(tstest.ClockOpts{})
+	sr := &ServiceReconciler{
+		Client: fc,
+		ssr: &tailscaleSTSReconciler{
+			Client:            fc,
+			tsClient:          ft,
+			operatorNamespace: "operator-ns",
+		},
+		logger: zl.Sugar(),
+		clock:  clock,
+	}
+	expectReconciled(t, sr, "default", "test")
+	fullName, shortName := findGenName(t, fc, "default", "test", "svc")
+	opts := configOpts{
+		stsName:            shortName,
+		secretName:         fullName,
+		namespace:          "default",
+		parentType:         "svc",
+		tailscaleNamespace: "operator-ns",
+		hostname:           "default-test",
+		namespaced:         true,
+		proxyType:          proxyTypeIngressService,
+		app:                kubetypes.AppIngressProxy,
+		resourceVersion:    "1",
+	}
+
+	// 1. Enable metrics- expect metrics Service to be created
+	mustUpdate(t, fc, "", "metrics", func(pc *tsapi.ProxyClass) {
+		pc.Spec = tsapi.ProxyClassSpec{Metrics: &tsapi.Metrics{Enable: true}}
+	})
+	expectReconciled(t, sr, "default", "test")
+	opts.enableMetrics = true
+	expectEqual(t, fc, expectedMetricsService(opts))
+
+	// 2. Enable ServiceMonitor - should not error when there is no ServiceMonitor CRD in cluster
+	mustUpdate(t, fc, "", "metrics", func(pc *tsapi.ProxyClass) {
+		pc.Spec.Metrics.ServiceMonitor = &tsapi.ServiceMonitor{Enable: true}
+	})
+	expectReconciled(t, sr, "default", "test")
+
+	// 3. Create ServiceMonitor CRD and reconcile- ServiceMonitor should get created
+	mustCreate(t, fc, crd)
+	expectReconciled(t, sr, "default", "test")
+	expectEqualUnstructured(t, fc, expectedServiceMonitor(t, opts))
+
+	// 4. A change to ServiceMonitor config gets reflected in the ServiceMonitor resource
+	mustUpdate(t, fc, "", "metrics", func(pc *tsapi.ProxyClass) {
+		pc.Spec.Metrics.ServiceMonitor.Labels = tsapi.Labels{"foo": "bar"}
+	})
+	expectReconciled(t, sr, "default", "test")
+	opts.serviceMonitorLabels = tsapi.Labels{"foo": "bar"}
+	opts.resourceVersion = "2"
+	expectEqual(t, fc, expectedMetricsService(opts))
+	expectEqualUnstructured(t, fc, expectedServiceMonitor(t, opts))
+
+	// 5. Disable metrics- expect metrics Service to be deleted
+	mustUpdate(t, fc, "", "metrics", func(pc *tsapi.ProxyClass) {
+		pc.Spec.Metrics = nil
+	})
+	expectReconciled(t, sr, "default", "test")
+	expectMissing[corev1.Service](t, fc, "operator-ns", metricsResourceName(opts.stsName))
+	// ServiceMonitor gets garbage collected when Service gets deleted (it has OwnerReference of the Service
+	// object). We cannot test this using the fake client.
 }
 
 func toFQDN(t *testing.T, s string) dnsname.FQDN {

cmd/k8s-operator/proxy.go

@@ -311,7 +311,7 @@ func (h *apiserverProxy) addImpersonationHeadersAsRequired(r *http.Request) {
 
 	// Now add the impersonation headers that we want.
 	if err := addImpersonationHeaders(r, h.log); err != nil {
-		log.Printf("failed to add impersonation headers: " + err.Error())
+		log.Print("failed to add impersonation headers: ", err.Error())
 	}
 }
 

cmd/k8s-operator/proxyclass.go

@@ -15,6 +15,7 @@ import (
 	dockerref "github.com/distribution/reference"
 	"go.uber.org/zap"
 	corev1 "k8s.io/api/core/v1"
+	apiextensionsv1 "k8s.io/apiextensions-apiserver/pkg/apis/apiextensions/v1"
 	apiequality "k8s.io/apimachinery/pkg/api/equality"
 	apierrors "k8s.io/apimachinery/pkg/api/errors"
 	apivalidation "k8s.io/apimachinery/pkg/api/validation"
@@ -95,14 +96,14 @@ func (pcr *ProxyClassReconciler) Reconcile(ctx context.Context, req reconcile.Re
 	pcr.mu.Unlock()
 
 	oldPCStatus := pc.Status.DeepCopy()
-	if errs := pcr.validate(pc); errs != nil {
+	if errs := pcr.validate(ctx, pc); errs != nil {
 		msg := fmt.Sprintf(messageProxyClassInvalid, errs.ToAggregate().Error())
 		pcr.recorder.Event(pc, corev1.EventTypeWarning, reasonProxyClassInvalid, msg)
 		tsoperator.SetProxyClassCondition(pc, tsapi.ProxyClassReady, metav1.ConditionFalse, reasonProxyClassInvalid, msg, pc.Generation, pcr.clock, logger)
 	} else {
 		tsoperator.SetProxyClassCondition(pc, tsapi.ProxyClassReady, metav1.ConditionTrue, reasonProxyClassValid, reasonProxyClassValid, pc.Generation, pcr.clock, logger)
 	}
-	if !apiequality.Semantic.DeepEqual(oldPCStatus, pc.Status) {
+	if !apiequality.Semantic.DeepEqual(oldPCStatus, &pc.Status) {
 		if err := pcr.Client.Status().Update(ctx, pc); err != nil {
 			logger.Errorf("error updating ProxyClass status: %v", err)
 			return reconcile.Result{}, err
@@ -111,10 +112,10 @@ func (pcr *ProxyClassReconciler) Reconcile(ctx context.Context, req reconcile.Re
 	return reconcile.Result{}, nil
 }
 
-func (pcr *ProxyClassReconciler) validate(pc *tsapi.ProxyClass) (violations field.ErrorList) {
+func (pcr *ProxyClassReconciler) validate(ctx context.Context, pc *tsapi.ProxyClass) (violations field.ErrorList) {
 	if sts := pc.Spec.StatefulSet; sts != nil {
 		if len(sts.Labels) > 0 {
-			if errs := metavalidation.ValidateLabels(sts.Labels, field.NewPath(".spec.statefulSet.labels")); errs != nil {
+			if errs := metavalidation.ValidateLabels(sts.Labels.Parse(), field.NewPath(".spec.statefulSet.labels")); errs != nil {
 				violations = append(violations, errs...)
 			}
 		}
@@ -125,7 +126,7 @@ func (pcr *ProxyClassReconciler) validate(pc *tsapi.ProxyClass) (violations fiel
 		}
 		if pod := sts.Pod; pod != nil {
 			if len(pod.Labels) > 0 {
-				if errs := metavalidation.ValidateLabels(pod.Labels, field.NewPath(".spec.statefulSet.pod.labels")); errs != nil {
+				if errs := metavalidation.ValidateLabels(pod.Labels.Parse(), field.NewPath(".spec.statefulSet.pod.labels")); errs != nil {
 					violations = append(violations, errs...)
 				}
 			}
@@ -160,9 +161,28 @@ func (pcr *ProxyClassReconciler) validate(pc *tsapi.ProxyClass) (violations fiel
 						violations = append(violations, field.TypeInvalid(field.NewPath("spec", "statefulSet", "pod", "tailscaleInitContainer", "image"), tc.Image, err.Error()))
 					}
 				}
+
+				if tc.Debug != nil {
+					violations = append(violations, field.TypeInvalid(field.NewPath("spec", "statefulSet", "pod", "tailscaleInitContainer", "debug"), tc.Debug, "debug settings cannot be configured on the init container"))
+				}
 			}
 		}
 	}
+	if pc.Spec.Metrics != nil && pc.Spec.Metrics.ServiceMonitor != nil && pc.Spec.Metrics.ServiceMonitor.Enable {
+		found, err := hasServiceMonitorCRD(ctx, pcr.Client)
+		if err != nil {
+			pcr.logger.Infof("[unexpected]: error retrieving %q CRD: %v", serviceMonitorCRD, err)
+			// best effort validation - don't error out here
+		} else if !found {
+			msg := fmt.Sprintf("ProxyClass defines that a ServiceMonitor custom resource should be created, but %q CRD was not found", serviceMonitorCRD)
+			violations = append(violations, field.TypeInvalid(field.NewPath("spec", "metrics", "serviceMonitor"), "enable", msg))
+		}
+	}
+	if pc.Spec.Metrics != nil && pc.Spec.Metrics.ServiceMonitor != nil && len(pc.Spec.Metrics.ServiceMonitor.Labels) > 0 {
+		if errs := metavalidation.ValidateLabels(pc.Spec.Metrics.ServiceMonitor.Labels.Parse(), field.NewPath(".spec.metrics.serviceMonitor.labels")); errs != nil {
+			violations = append(violations, errs...)
+		}
+	}
 	// We do not validate embedded fields (security context, resource
 	// requirements etc) as we inherit upstream validation for those fields.
 	// Invalid values would get rejected by upstream validations at apply
@@ -170,6 +190,16 @@ func (pcr *ProxyClassReconciler) validate(pc *tsapi.ProxyClass) (violations fiel
 	return violations
 }
 
+func hasServiceMonitorCRD(ctx context.Context, cl client.Client) (bool, error) {
+	sm := &apiextensionsv1.CustomResourceDefinition{}
+	if err := cl.Get(ctx, types.NamespacedName{Name: serviceMonitorCRD}, sm); apierrors.IsNotFound(err) {
+		return false, nil
+	} else if err != nil {
+		return false, err
+	}
+	return true, nil
+}
+
 // maybeCleanup removes tailscale.com finalizer and ensures that the ProxyClass
 // is no longer counted towards k8s_proxyclass_resources.
 func (pcr *ProxyClassReconciler) maybeCleanup(ctx context.Context, logger *zap.SugaredLogger, pc *tsapi.ProxyClass) error {

cmd/k8s-operator/proxyclass_test.go

@@ -8,10 +8,12 @@
 package main
 
 import (
+	"context"
 	"testing"
 	"time"
 
 	"go.uber.org/zap"
+	apiextensionsv1 "k8s.io/apiextensions-apiserver/pkg/apis/apiextensions/v1"
 	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
 	"k8s.io/apimachinery/pkg/types"
 	"k8s.io/client-go/tools/record"
@@ -34,10 +36,10 @@ func TestProxyClass(t *testing.T) {
 		},
 		Spec: tsapi.ProxyClassSpec{
 			StatefulSet: &tsapi.StatefulSet{
-				Labels:      map[string]string{"foo": "bar", "xyz1234": "abc567"},
+				Labels:      tsapi.Labels{"foo": "bar", "xyz1234": "abc567"},
 				Annotations: map[string]string{"foo.io/bar": "{'key': 'val1232'}"},
 				Pod: &tsapi.Pod{
-					Labels:      map[string]string{"foo": "bar", "xyz1234": "abc567"},
+					Labels:      tsapi.Labels{"foo": "bar", "xyz1234": "abc567"},
 					Annotations: map[string]string{"foo.io/bar": "{'key': 'val1232'}"},
 					TailscaleContainer: &tsapi.Container{
 						Env:             []tsapi.Env{{Name: "FOO", Value: "BAR"}},
@@ -76,7 +78,7 @@ func TestProxyClass(t *testing.T) {
 		LastTransitionTime: metav1.Time{Time: cl.Now().Truncate(time.Second)},
 	})
 
-	expectEqual(t, fc, pc, nil)
+	expectEqual(t, fc, pc)
 
 	// 2. A ProxyClass resource with invalid labels gets its status updated to Invalid with an error message.
 	pc.Spec.StatefulSet.Labels["foo"] = "?!someVal"
@@ -86,7 +88,7 @@ func TestProxyClass(t *testing.T) {
 	expectReconciled(t, pcr, "", "test")
 	msg := `ProxyClass is not valid: .spec.statefulSet.labels: Invalid value: "?!someVal": a valid label must be an empty string or consist of alphanumeric characters, '-', '_' or '.', and must start and end with an alphanumeric character (e.g. 'MyValue',  or 'my_value',  or '12345', regex used for validation is '(([A-Za-z0-9][-A-Za-z0-9_.]*)?[A-Za-z0-9])?')`
 	tsoperator.SetProxyClassCondition(pc, tsapi.ProxyClassReady, metav1.ConditionFalse, reasonProxyClassInvalid, msg, 0, cl, zl.Sugar())
-	expectEqual(t, fc, pc, nil)
+	expectEqual(t, fc, pc)
 	expectedEvent := "Warning ProxyClassInvalid ProxyClass is not valid: .spec.statefulSet.labels: Invalid value: \"?!someVal\": a valid label must be an empty string or consist of alphanumeric characters, '-', '_' or '.', and must start and end with an alphanumeric character (e.g. 'MyValue',  or 'my_value',  or '12345', regex used for validation is '(([A-Za-z0-9][-A-Za-z0-9_.]*)?[A-Za-z0-9])?')"
 	expectEvents(t, fr, []string{expectedEvent})
 
@@ -100,7 +102,7 @@ func TestProxyClass(t *testing.T) {
 	expectReconciled(t, pcr, "", "test")
 	msg = `ProxyClass is not valid: spec.statefulSet.pod.tailscaleContainer.image: Invalid value: "FOO bar": invalid reference format: repository name (library/FOO bar) must be lowercase`
 	tsoperator.SetProxyClassCondition(pc, tsapi.ProxyClassReady, metav1.ConditionFalse, reasonProxyClassInvalid, msg, 0, cl, zl.Sugar())
-	expectEqual(t, fc, pc, nil)
+	expectEqual(t, fc, pc)
 	expectedEvent = `Warning ProxyClassInvalid ProxyClass is not valid: spec.statefulSet.pod.tailscaleContainer.image: Invalid value: "FOO bar": invalid reference format: repository name (library/FOO bar) must be lowercase`
 	expectEvents(t, fr, []string{expectedEvent})
 
@@ -119,7 +121,7 @@ func TestProxyClass(t *testing.T) {
 	expectReconciled(t, pcr, "", "test")
 	msg = `ProxyClass is not valid: spec.statefulSet.pod.tailscaleInitContainer.image: Invalid value: "FOO bar": invalid reference format: repository name (library/FOO bar) must be lowercase`
 	tsoperator.SetProxyClassCondition(pc, tsapi.ProxyClassReady, metav1.ConditionFalse, reasonProxyClassInvalid, msg, 0, cl, zl.Sugar())
-	expectEqual(t, fc, pc, nil)
+	expectEqual(t, fc, pc)
 	expectedEvent = `Warning ProxyClassInvalid ProxyClass is not valid: spec.statefulSet.pod.tailscaleInitContainer.image: Invalid value: "FOO bar": invalid reference format: repository name (library/FOO bar) must be lowercase`
 	expectEvents(t, fr, []string{expectedEvent})
 
@@ -134,4 +136,95 @@ func TestProxyClass(t *testing.T) {
 		"Warning CustomTSEnvVar ProxyClass overrides the default value for EXPERIMENTAL_ALLOW_PROXYING_CLUSTER_TRAFFIC_VIA_INGRESS env var for tailscale container. Running with custom values for Tailscale env vars is not recommended and might break in the future."}
 	expectReconciled(t, pcr, "", "test")
 	expectEvents(t, fr, expectedEvents)
+
+	// 6. A ProxyClass with ServiceMonitor enabled and in a cluster that has not ServiceMonitor CRD is invalid
+	pc.Spec.Metrics = &tsapi.Metrics{Enable: true, ServiceMonitor: &tsapi.ServiceMonitor{Enable: true}}
+	mustUpdate(t, fc, "", "test", func(proxyClass *tsapi.ProxyClass) {
+		proxyClass.Spec = pc.Spec
+	})
+	expectReconciled(t, pcr, "", "test")
+	msg = `ProxyClass is not valid: spec.metrics.serviceMonitor: Invalid value: "enable": ProxyClass defines that a ServiceMonitor custom resource should be created, but "servicemonitors.monitoring.coreos.com" CRD was not found`
+	tsoperator.SetProxyClassCondition(pc, tsapi.ProxyClassReady, metav1.ConditionFalse, reasonProxyClassInvalid, msg, 0, cl, zl.Sugar())
+	expectEqual(t, fc, pc)
+	expectedEvent = "Warning ProxyClassInvalid " + msg
+	expectEvents(t, fr, []string{expectedEvent})
+
+	// 7. A ProxyClass with ServiceMonitor enabled and in a cluster that does have the ServiceMonitor CRD is valid
+	crd := &apiextensionsv1.CustomResourceDefinition{ObjectMeta: metav1.ObjectMeta{Name: serviceMonitorCRD}}
+	mustCreate(t, fc, crd)
+	expectReconciled(t, pcr, "", "test")
+	tsoperator.SetProxyClassCondition(pc, tsapi.ProxyClassReady, metav1.ConditionTrue, reasonProxyClassValid, reasonProxyClassValid, 0, cl, zl.Sugar())
+	expectEqual(t, fc, pc)
+
+	// 7. A ProxyClass with invalid ServiceMonitor labels gets its status updated to Invalid with an error message.
+	pc.Spec.Metrics.ServiceMonitor.Labels = tsapi.Labels{"foo": "bar!"}
+	mustUpdate(t, fc, "", "test", func(proxyClass *tsapi.ProxyClass) {
+		proxyClass.Spec.Metrics.ServiceMonitor.Labels = pc.Spec.Metrics.ServiceMonitor.Labels
+	})
+	expectReconciled(t, pcr, "", "test")
+	msg = `ProxyClass is not valid: .spec.metrics.serviceMonitor.labels: Invalid value: "bar!": a valid label must be an empty string or consist of alphanumeric characters, '-', '_' or '.', and must start and end with an alphanumeric character (e.g. 'MyValue',  or 'my_value',  or '12345', regex used for validation is '(([A-Za-z0-9][-A-Za-z0-9_.]*)?[A-Za-z0-9])?')`
+	tsoperator.SetProxyClassCondition(pc, tsapi.ProxyClassReady, metav1.ConditionFalse, reasonProxyClassInvalid, msg, 0, cl, zl.Sugar())
+	expectEqual(t, fc, pc)
+
+	// 8. A ProxyClass with valid ServiceMonitor labels gets its status updated to Valid.
+	pc.Spec.Metrics.ServiceMonitor.Labels = tsapi.Labels{"foo": "bar", "xyz1234": "abc567", "empty": "", "onechar": "a"}
+	mustUpdate(t, fc, "", "test", func(proxyClass *tsapi.ProxyClass) {
+		proxyClass.Spec.Metrics.ServiceMonitor.Labels = pc.Spec.Metrics.ServiceMonitor.Labels
+	})
+	expectReconciled(t, pcr, "", "test")
+	tsoperator.SetProxyClassCondition(pc, tsapi.ProxyClassReady, metav1.ConditionTrue, reasonProxyClassValid, reasonProxyClassValid, 0, cl, zl.Sugar())
+	expectEqual(t, fc, pc)
+}
+
+func TestValidateProxyClass(t *testing.T) {
+	for name, tc := range map[string]struct {
+		pc    *tsapi.ProxyClass
+		valid bool
+	}{
+		"empty": {
+			valid: true,
+			pc:    &tsapi.ProxyClass{},
+		},
+		"debug_enabled_for_main_container": {
+			valid: true,
+			pc: &tsapi.ProxyClass{
+				Spec: tsapi.ProxyClassSpec{
+					StatefulSet: &tsapi.StatefulSet{
+						Pod: &tsapi.Pod{
+							TailscaleContainer: &tsapi.Container{
+								Debug: &tsapi.Debug{
+									Enable: true,
+								},
+							},
+						},
+					},
+				},
+			},
+		},
+		"debug_enabled_for_init_container": {
+			valid: false,
+			pc: &tsapi.ProxyClass{
+				Spec: tsapi.ProxyClassSpec{
+					StatefulSet: &tsapi.StatefulSet{
+						Pod: &tsapi.Pod{
+							TailscaleInitContainer: &tsapi.Container{
+								Debug: &tsapi.Debug{
+									Enable: true,
+								},
+							},
+						},
+					},
+				},
+			},
+		},
+	} {
+		t.Run(name, func(t *testing.T) {
+			pcr := &ProxyClassReconciler{}
+			err := pcr.validate(context.Background(), tc.pc)
+			valid := err == nil
+			if valid != tc.valid {
+				t.Errorf("expected valid=%v, got valid=%v, err=%v", tc.valid, valid, err)
+			}
+		})
+	}
 }

cmd/k8s-operator/proxygroup.go

@@ -12,6 +12,7 @@ import (
 	"fmt"
 	"net/http"
 	"slices"
+	"strings"
 	"sync"
 
 	"github.com/pkg/errors"
@@ -45,9 +46,15 @@ const (
 	reasonProxyGroupReady          = "ProxyGroupReady"
 	reasonProxyGroupCreating       = "ProxyGroupCreating"
 	reasonProxyGroupInvalid        = "ProxyGroupInvalid"
+
+	// Copied from k8s.io/apiserver/pkg/registry/generic/registry/store.go@cccad306d649184bf2a0e319ba830c53f65c445c
+	optimisticLockErrorMsg = "the object has been modified; please apply your changes to the latest version and try again"
 )
 
-var gaugeProxyGroupResources = clientmetric.NewGauge(kubetypes.MetricProxyGroupCount)
+var (
+	gaugeEgressProxyGroupResources  = clientmetric.NewGauge(kubetypes.MetricProxyGroupEgressCount)
+	gaugeIngressProxyGroupResources = clientmetric.NewGauge(kubetypes.MetricProxyGroupIngressCount)
+)
 
 // ProxyGroupReconciler ensures cluster resources for a ProxyGroup definition.
 type ProxyGroupReconciler struct {
@@ -64,8 +71,9 @@ type ProxyGroupReconciler struct {
 	tsFirewallMode    string
 	defaultProxyClass string
 
-	mu          sync.Mutex           // protects following
-	proxyGroups set.Slice[types.UID] // for proxygroups gauge
+	mu                 sync.Mutex           // protects following
+	egressProxyGroups  set.Slice[types.UID] // for egress proxygroups gauge
+	ingressProxyGroups set.Slice[types.UID] // for ingress proxygroups gauge
 }
 
 func (r *ProxyGroupReconciler) logger(name string) *zap.SugaredLogger {
@@ -110,7 +118,7 @@ func (r *ProxyGroupReconciler) Reconcile(ctx context.Context, req reconcile.Requ
 	oldPGStatus := pg.Status.DeepCopy()
 	setStatusReady := func(pg *tsapi.ProxyGroup, status metav1.ConditionStatus, reason, message string) (reconcile.Result, error) {
 		tsoperator.SetProxyGroupCondition(pg, tsapi.ProxyGroupReady, status, reason, message, pg.Generation, r.clock, logger)
-		if !apiequality.Semantic.DeepEqual(oldPGStatus, pg.Status) {
+		if !apiequality.Semantic.DeepEqual(oldPGStatus, &pg.Status) {
 			// An error encountered here should get returned by the Reconcile function.
 			if updateErr := r.Client.Status().Update(ctx, pg); updateErr != nil {
 				err = errors.Wrap(err, updateErr.Error())
@@ -166,9 +174,17 @@ func (r *ProxyGroupReconciler) Reconcile(ctx context.Context, req reconcile.Requ
 	}
 
 	if err = r.maybeProvision(ctx, pg, proxyClass); err != nil {
-		err = fmt.Errorf("error provisioning ProxyGroup resources: %w", err)
-		r.recorder.Eventf(pg, corev1.EventTypeWarning, reasonProxyGroupCreationFailed, err.Error())
-		return setStatusReady(pg, metav1.ConditionFalse, reasonProxyGroupCreationFailed, err.Error())
+		reason := reasonProxyGroupCreationFailed
+		msg := fmt.Sprintf("error provisioning ProxyGroup resources: %s", err)
+		if strings.Contains(err.Error(), optimisticLockErrorMsg) {
+			reason = reasonProxyGroupCreating
+			msg = fmt.Sprintf("optimistic lock error, retrying: %s", err)
+			err = nil
+			logger.Info(msg)
+		} else {
+			r.recorder.Eventf(pg, corev1.EventTypeWarning, reason, msg)
+		}
+		return setStatusReady(pg, metav1.ConditionFalse, reason, msg)
 	}
 
 	desiredReplicas := int(pgReplicas(pg))
@@ -191,8 +207,7 @@ func (r *ProxyGroupReconciler) Reconcile(ctx context.Context, req reconcile.Requ
 func (r *ProxyGroupReconciler) maybeProvision(ctx context.Context, pg *tsapi.ProxyGroup, proxyClass *tsapi.ProxyClass) error {
 	logger := r.logger(pg.Name)
 	r.mu.Lock()
-	r.proxyGroups.Add(pg.UID)
-	gaugeProxyGroupResources.Set(int64(r.proxyGroups.Len()))
+	r.ensureAddedToGaugeForProxyGroup(pg)
 	r.mu.Unlock()
 
 	cfgHash, err := r.ensureConfigSecretsCreated(ctx, pg, proxyClass)
@@ -243,22 +258,67 @@ func (r *ProxyGroupReconciler) maybeProvision(ctx context.Context, pg *tsapi.Pro
 			existing.ObjectMeta.Labels = cm.ObjectMeta.Labels
 			existing.ObjectMeta.OwnerReferences = cm.ObjectMeta.OwnerReferences
 		}); err != nil {
-			return fmt.Errorf("error provisioning ConfigMap: %w", err)
+			return fmt.Errorf("error provisioning egress ConfigMap %q: %w", cm.Name, err)
 		}
 	}
-	ss, err := pgStatefulSet(pg, r.tsNamespace, r.proxyImage, r.tsFirewallMode, cfgHash)
+	if pg.Spec.Type == tsapi.ProxyGroupTypeIngress {
+		cm := pgIngressCM(pg, r.tsNamespace)
+		if _, err := createOrUpdate(ctx, r.Client, r.tsNamespace, cm, func(existing *corev1.ConfigMap) {
+			existing.ObjectMeta.Labels = cm.ObjectMeta.Labels
+			existing.ObjectMeta.OwnerReferences = cm.ObjectMeta.OwnerReferences
+		}); err != nil {
+			return fmt.Errorf("error provisioning ingress ConfigMap %q: %w", cm.Name, err)
+		}
+	}
+	ss, err := pgStatefulSet(pg, r.tsNamespace, r.proxyImage, r.tsFirewallMode)
 	if err != nil {
 		return fmt.Errorf("error generating StatefulSet spec: %w", err)
 	}
 	ss = applyProxyClassToStatefulSet(proxyClass, ss, nil, logger)
-	if _, err := createOrUpdate(ctx, r.Client, r.tsNamespace, ss, func(s *appsv1.StatefulSet) {
+	capver, err := r.capVerForPG(ctx, pg, logger)
+	if err != nil {
+		return fmt.Errorf("error getting device info: %w", err)
+	}
+
+	updateSS := func(s *appsv1.StatefulSet) {
+
+		// This is a temporary workaround to ensure that egress ProxyGroup proxies with capver older than 110
+		// are restarted when tailscaled configfile contents have changed.
+		// This workaround ensures that:
+		// 1. The hash mechanism is used to trigger pod restarts for proxies below capver 110.
+		// 2. Proxies above capver are not unnecessarily restarted when the configfile contents change.
+		// 3. If the hash has alreay been set, but the capver is above 110, the old hash is preserved to avoid
+		// unnecessary pod restarts that could result in an update loop where capver cannot be determined for a
+		// restarting Pod and the hash is re-added again.
+		// Note that this workaround is only applied to egress ProxyGroups, because ingress ProxyGroup was added after capver 110.
+		// Note also that the hash annotation is only set on updates, not creation, because if the StatefulSet is
+		// being created, there is no need for a restart.
+		// TODO(irbekrm): remove this in 1.84.
+		hash := cfgHash
+		if capver >= 110 {
+			hash = s.Spec.Template.GetAnnotations()[podAnnotationLastSetConfigFileHash]
+		}
+		s.Spec = ss.Spec
+		if hash != "" && pg.Spec.Type == tsapi.ProxyGroupTypeEgress {
+			mak.Set(&s.Spec.Template.Annotations, podAnnotationLastSetConfigFileHash, hash)
+		}
+
 		s.ObjectMeta.Labels = ss.ObjectMeta.Labels
 		s.ObjectMeta.Annotations = ss.ObjectMeta.Annotations
 		s.ObjectMeta.OwnerReferences = ss.ObjectMeta.OwnerReferences
-		s.Spec = ss.Spec
-	}); err != nil {
+	}
+	if _, err := createOrUpdate(ctx, r.Client, r.tsNamespace, ss, updateSS); err != nil {
 		return fmt.Errorf("error provisioning StatefulSet: %w", err)
 	}
+	mo := &metricsOpts{
+		tsNamespace:  r.tsNamespace,
+		proxyStsName: pg.Name,
+		proxyLabels:  pgLabels(pg.Name, nil),
+		proxyType:    "proxygroup",
+	}
+	if err := reconcileMetricsResources(ctx, logger, mo, proxyClass, r.Client); err != nil {
+		return fmt.Errorf("error reconciling metrics resources: %w", err)
+	}
 
 	if err := r.cleanupDanglingResources(ctx, pg); err != nil {
 		return fmt.Errorf("error cleaning up dangling resources: %w", err)
@@ -327,10 +387,17 @@ func (r *ProxyGroupReconciler) maybeCleanup(ctx context.Context, pg *tsapi.Proxy
 		}
 	}
 
+	mo := &metricsOpts{
+		proxyLabels: pgLabels(pg.Name, nil),
+		tsNamespace: r.tsNamespace,
+		proxyType:   "proxygroup"}
+	if err := maybeCleanupMetricsResources(ctx, mo, r.Client); err != nil {
+		return false, fmt.Errorf("error cleaning up metrics resources: %w", err)
+	}
+
 	logger.Infof("cleaned up ProxyGroup resources")
 	r.mu.Lock()
-	r.proxyGroups.Remove(pg.UID)
-	gaugeProxyGroupResources.Set(int64(r.proxyGroups.Len()))
+	r.ensureRemovedFromGaugeForProxyGroup(pg)
 	r.mu.Unlock()
 	return true, nil
 }
@@ -353,7 +420,7 @@ func (r *ProxyGroupReconciler) deleteTailnetDevice(ctx context.Context, id tailc
 
 func (r *ProxyGroupReconciler) ensureConfigSecretsCreated(ctx context.Context, pg *tsapi.ProxyGroup, proxyClass *tsapi.ProxyClass) (hash string, err error) {
 	logger := r.logger(pg.Name)
-	var allConfigs []tailscaledConfigs
+	var configSHA256Sum string
 	for i := range pgReplicas(pg) {
 		cfgSecret := &corev1.Secret{
 			ObjectMeta: metav1.ObjectMeta{
@@ -389,7 +456,6 @@ func (r *ProxyGroupReconciler) ensureConfigSecretsCreated(ctx context.Context, p
 		if err != nil {
 			return "", fmt.Errorf("error creating tailscaled config: %w", err)
 		}
-		allConfigs = append(allConfigs, configs)
 
 		for cap, cfg := range configs {
 			cfgJSON, err := json.Marshal(cfg)
@@ -399,6 +465,32 @@ func (r *ProxyGroupReconciler) ensureConfigSecretsCreated(ctx context.Context, p
 			mak.Set(&cfgSecret.StringData, tsoperator.TailscaledConfigFileName(cap), string(cfgJSON))
 		}
 
+		// The config sha256 sum is a value for a hash annotation used to trigger
+		// pod restarts when tailscaled config changes. Any config changes apply
+		// to all replicas, so it is sufficient to only hash the config for the
+		// first replica.
+		//
+		// In future, we're aiming to eliminate restarts altogether and have
+		// pods dynamically reload their config when it changes.
+		if i == 0 {
+			sum := sha256.New()
+			for _, cfg := range configs {
+				// Zero out the auth key so it doesn't affect the sha256 hash when we
+				// remove it from the config after the pods have all authed. Otherwise
+				// all the pods will need to restart immediately after authing.
+				cfg.AuthKey = nil
+				b, err := json.Marshal(cfg)
+				if err != nil {
+					return "", err
+				}
+				if _, err := sum.Write(b); err != nil {
+					return "", err
+				}
+			}
+
+			configSHA256Sum = fmt.Sprintf("%x", sum.Sum(nil))
+		}
+
 		if existingCfgSecret != nil {
 			logger.Debugf("patching the existing ProxyGroup config Secret %s", cfgSecret.Name)
 			if err := r.Patch(ctx, cfgSecret, client.MergeFrom(existingCfgSecret)); err != nil {
@@ -412,16 +504,33 @@ func (r *ProxyGroupReconciler) ensureConfigSecretsCreated(ctx context.Context, p
 		}
 	}
 
-	sum := sha256.New()
-	b, err := json.Marshal(allConfigs)
-	if err != nil {
-		return "", err
-	}
-	if _, err := sum.Write(b); err != nil {
-		return "", err
-	}
+	return configSHA256Sum, nil
+}
 
-	return fmt.Sprintf("%x", sum.Sum(nil)), nil
+// ensureAddedToGaugeForProxyGroup ensures the gauge metric for the ProxyGroup resource is updated when the ProxyGroup
+// is created. r.mu must be held.
+func (r *ProxyGroupReconciler) ensureAddedToGaugeForProxyGroup(pg *tsapi.ProxyGroup) {
+	switch pg.Spec.Type {
+	case tsapi.ProxyGroupTypeEgress:
+		r.egressProxyGroups.Add(pg.UID)
+	case tsapi.ProxyGroupTypeIngress:
+		r.ingressProxyGroups.Add(pg.UID)
+	}
+	gaugeEgressProxyGroupResources.Set(int64(r.egressProxyGroups.Len()))
+	gaugeIngressProxyGroupResources.Set(int64(r.ingressProxyGroups.Len()))
+}
+
+// ensureRemovedFromGaugeForProxyGroup ensures the gauge metric for the ProxyGroup resource type is updated when the
+// ProxyGroup is deleted. r.mu must be held.
+func (r *ProxyGroupReconciler) ensureRemovedFromGaugeForProxyGroup(pg *tsapi.ProxyGroup) {
+	switch pg.Spec.Type {
+	case tsapi.ProxyGroupTypeEgress:
+		r.egressProxyGroups.Remove(pg.UID)
+	case tsapi.ProxyGroupTypeIngress:
+		r.ingressProxyGroups.Remove(pg.UID)
+	}
+	gaugeEgressProxyGroupResources.Set(int64(r.egressProxyGroups.Len()))
+	gaugeIngressProxyGroupResources.Set(int64(r.ingressProxyGroups.Len()))
 }
 
 func pgTailscaledConfig(pg *tsapi.ProxyGroup, class *tsapi.ProxyClass, idx int32, authKey string, oldSecret *corev1.Secret) (tailscaledConfigs, error) {
@@ -434,7 +543,7 @@ func pgTailscaledConfig(pg *tsapi.ProxyGroup, class *tsapi.ProxyClass, idx int32
 	}
 
 	if pg.Spec.HostnamePrefix != "" {
-		conf.Hostname = ptr.To(fmt.Sprintf("%s%d", pg.Spec.HostnamePrefix, idx))
+		conf.Hostname = ptr.To(fmt.Sprintf("%s-%d", pg.Spec.HostnamePrefix, idx))
 	}
 
 	if shouldAcceptRoutes(class) {
@@ -491,12 +600,19 @@ func (r *ProxyGroupReconciler) getNodeMetadata(ctx context.Context, pg *tsapi.Pr
 			continue
 		}
 
-		metadata = append(metadata, nodeMetadata{
+		nm := nodeMetadata{
 			ordinal:     ordinal,
 			stateSecret: &secret,
 			tsID:        id,
 			dnsName:     dnsName,
-		})
+		}
+		pod := &corev1.Pod{}
+		if err := r.Get(ctx, client.ObjectKey{Namespace: r.tsNamespace, Name: secret.Name}, pod); err != nil && !apierrors.IsNotFound(err) {
+			return nil, err
+		} else if err == nil {
+			nm.podUID = string(pod.UID)
+		}
+		metadata = append(metadata, nm)
 	}
 
 	return metadata, nil
@@ -528,6 +644,29 @@ func (r *ProxyGroupReconciler) getDeviceInfo(ctx context.Context, pg *tsapi.Prox
 type nodeMetadata struct {
 	ordinal     int
 	stateSecret *corev1.Secret
-	tsID        tailcfg.StableNodeID
-	dnsName     string
+	// podUID is the UID of the current Pod or empty if the Pod does not exist.
+	podUID  string
+	tsID    tailcfg.StableNodeID
+	dnsName string
+}
+
+// capVerForPG returns best effort capability version for the given ProxyGroup. It attempts to find it by looking at the
+// Secret + Pod for the replica with ordinal 0. Returns -1 if it is not possible to determine the capability version
+// (i.e there is no Pod yet).
+func (r *ProxyGroupReconciler) capVerForPG(ctx context.Context, pg *tsapi.ProxyGroup, logger *zap.SugaredLogger) (tailcfg.CapabilityVersion, error) {
+	metas, err := r.getNodeMetadata(ctx, pg)
+	if err != nil {
+		return -1, fmt.Errorf("error getting node metadata: %w", err)
+	}
+	if len(metas) == 0 {
+		return -1, nil
+	}
+	dev, err := deviceInfo(metas[0].stateSecret, metas[0].podUID, logger)
+	if err != nil {
+		return -1, fmt.Errorf("error getting device info: %w", err)
+	}
+	if dev == nil {
+		return -1, nil
+	}
+	return dev.capver, nil
 }

cmd/k8s-operator/proxygroup_specs.go

@@ -15,12 +15,13 @@ import (
 	"sigs.k8s.io/yaml"
 	tsapi "tailscale.com/k8s-operator/apis/v1alpha1"
 	"tailscale.com/kube/egressservices"
+	"tailscale.com/kube/kubetypes"
 	"tailscale.com/types/ptr"
 )
 
 // Returns the base StatefulSet definition for a ProxyGroup. A ProxyClass may be
 // applied over the top after.
-func pgStatefulSet(pg *tsapi.ProxyGroup, namespace, image, tsFirewallMode, cfgHash string) (*appsv1.StatefulSet, error) {
+func pgStatefulSet(pg *tsapi.ProxyGroup, namespace, image, tsFirewallMode string) (*appsv1.StatefulSet, error) {
 	ss := new(appsv1.StatefulSet)
 	if err := yaml.Unmarshal(proxyYaml, &ss); err != nil {
 		return nil, fmt.Errorf("failed to unmarshal proxy spec: %w", err)
@@ -52,12 +53,13 @@ func pgStatefulSet(pg *tsapi.ProxyGroup, namespace, image, tsFirewallMode, cfgHa
 		Namespace:                  namespace,
 		Labels:                     pgLabels(pg.Name, nil),
 		DeletionGracePeriodSeconds: ptr.To[int64](10),
-		Annotations: map[string]string{
-			podAnnotationLastSetConfigFileHash: cfgHash,
-		},
 	}
 	tmpl.Spec.ServiceAccountName = pg.Name
 	tmpl.Spec.InitContainers[0].Image = image
+	proxyConfigVolName := pgEgressCMName(pg.Name)
+	if pg.Spec.Type == tsapi.ProxyGroupTypeIngress {
+		proxyConfigVolName = pgIngressCMName(pg.Name)
+	}
 	tmpl.Spec.Volumes = func() []corev1.Volume {
 		var volumes []corev1.Volume
 		for i := range pgReplicas(pg) {
@@ -71,18 +73,16 @@ func pgStatefulSet(pg *tsapi.ProxyGroup, namespace, image, tsFirewallMode, cfgHa
 			})
 		}
 
-		if pg.Spec.Type == tsapi.ProxyGroupTypeEgress {
-			volumes = append(volumes, corev1.Volume{
-				Name: pgEgressCMName(pg.Name),
-				VolumeSource: corev1.VolumeSource{
-					ConfigMap: &corev1.ConfigMapVolumeSource{
-						LocalObjectReference: corev1.LocalObjectReference{
-							Name: pgEgressCMName(pg.Name),
-						},
+		volumes = append(volumes, corev1.Volume{
+			Name: proxyConfigVolName,
+			VolumeSource: corev1.VolumeSource{
+				ConfigMap: &corev1.ConfigMapVolumeSource{
+					LocalObjectReference: corev1.LocalObjectReference{
+						Name: proxyConfigVolName,
 					},
 				},
-			})
-		}
+			},
+		})
 
 		return volumes
 	}()
@@ -92,6 +92,10 @@ func pgStatefulSet(pg *tsapi.ProxyGroup, namespace, image, tsFirewallMode, cfgHa
 	c.Image = image
 	c.VolumeMounts = func() []corev1.VolumeMount {
 		var mounts []corev1.VolumeMount
+
+		// TODO(tomhjp): Read config directly from the secret instead. The
+		// mounts change on scaling up/down which causes unnecessary restarts
+		// for pods that haven't meaningfully changed.
 		for i := range pgReplicas(pg) {
 			mounts = append(mounts, corev1.VolumeMount{
 				Name:      fmt.Sprintf("tailscaledconfig-%d", i),
@@ -100,13 +104,11 @@ func pgStatefulSet(pg *tsapi.ProxyGroup, namespace, image, tsFirewallMode, cfgHa
 			})
 		}
 
-		if pg.Spec.Type == tsapi.ProxyGroupTypeEgress {
-			mounts = append(mounts, corev1.VolumeMount{
-				Name:      pgEgressCMName(pg.Name),
-				MountPath: "/etc/proxies",
-				ReadOnly:  true,
-			})
-		}
+		mounts = append(mounts, corev1.VolumeMount{
+			Name:      proxyConfigVolName,
+			MountPath: "/etc/proxies",
+			ReadOnly:  true,
+		})
 
 		return mounts
 	}()
@@ -121,15 +123,6 @@ func pgStatefulSet(pg *tsapi.ProxyGroup, namespace, image, tsFirewallMode, cfgHa
 					},
 				},
 			},
-			{
-				Name: "POD_NAME",
-				ValueFrom: &corev1.EnvVarSource{
-					FieldRef: &corev1.ObjectFieldSelector{
-						// Secret is named after the pod.
-						FieldPath: "metadata.name",
-					},
-				},
-			},
 			{
 				Name:  "TS_KUBE_SECRET",
 				Value: "$(POD_NAME)",
@@ -142,10 +135,6 @@ func pgStatefulSet(pg *tsapi.ProxyGroup, namespace, image, tsFirewallMode, cfgHa
 				Name:  "TS_EXPERIMENTAL_VERSIONED_CONFIG_DIR",
 				Value: "/etc/tsconfig/$(POD_NAME)",
 			},
-			{
-				Name:  "TS_USERSPACE",
-				Value: "false",
-			},
 		}
 
 		if tsFirewallMode != "" {
@@ -159,10 +148,23 @@ func pgStatefulSet(pg *tsapi.ProxyGroup, namespace, image, tsFirewallMode, cfgHa
 			envs = append(envs, corev1.EnvVar{
 				Name:  "TS_EGRESS_SERVICES_CONFIG_PATH",
 				Value: fmt.Sprintf("/etc/proxies/%s", egressservices.KeyEgressServices),
-			})
+			},
+				corev1.EnvVar{
+					Name:  "TS_INTERNAL_APP",
+					Value: kubetypes.AppProxyGroupEgress,
+				},
+			)
+		} else { // ingress
+			envs = append(envs, corev1.EnvVar{
+				Name:  "TS_INTERNAL_APP",
+				Value: kubetypes.AppProxyGroupIngress,
+			},
+				corev1.EnvVar{
+					Name:  "TS_SERVE_CONFIG",
+					Value: fmt.Sprintf("/etc/proxies/%s", serveConfigKey),
+				})
 		}
-
-		return envs
+		return append(c.Env, envs...)
 	}()
 
 	return ss, nil
@@ -206,6 +208,15 @@ func pgRole(pg *tsapi.ProxyGroup, namespace string) *rbacv1.Role {
 					return secrets
 				}(),
 			},
+			{
+				APIGroups: []string{""},
+				Resources: []string{"events"},
+				Verbs: []string{
+					"create",
+					"patch",
+					"get",
+				},
+			},
 		},
 	}
 }
@@ -257,6 +268,16 @@ func pgEgressCM(pg *tsapi.ProxyGroup, namespace string) *corev1.ConfigMap {
 		},
 	}
 }
+func pgIngressCM(pg *tsapi.ProxyGroup, namespace string) *corev1.ConfigMap {
+	return &corev1.ConfigMap{
+		ObjectMeta: metav1.ObjectMeta{
+			Name:            pgIngressCMName(pg.Name),
+			Namespace:       namespace,
+			Labels:          pgLabels(pg.Name, nil),
+			OwnerReferences: pgOwnerReference(pg),
+		},
+	}
+}
 
 func pgSecretLabels(pgName, typ string) map[string]string {
 	return pgLabels(pgName, map[string]string{

cmd/k8s-operator/proxygroup_test.go

@@ -17,6 +17,7 @@ import (
 	appsv1 "k8s.io/api/apps/v1"
 	corev1 "k8s.io/api/core/v1"
 	rbacv1 "k8s.io/api/rbac/v1"
+	apiextensionsv1 "k8s.io/apiextensions-apiserver/pkg/apis/apiextensions/v1"
 	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
 	"k8s.io/client-go/tools/record"
 	"sigs.k8s.io/controller-runtime/pkg/client"
@@ -24,8 +25,11 @@ import (
 	"tailscale.com/client/tailscale"
 	tsoperator "tailscale.com/k8s-operator"
 	tsapi "tailscale.com/k8s-operator/apis/v1alpha1"
+	"tailscale.com/kube/egressservices"
+	"tailscale.com/kube/kubetypes"
 	"tailscale.com/tstest"
 	"tailscale.com/types/ptr"
+	"tailscale.com/util/mak"
 )
 
 const testProxyImage = "tailscale/tailscale:test"
@@ -35,6 +39,8 @@ var defaultProxyClassAnnotations = map[string]string{
 }
 
 func TestProxyGroup(t *testing.T) {
+	const initialCfgHash = "6632726be70cf224049580deb4d317bba065915b5fd415461d60ed621c91b196"
+
 	pc := &tsapi.ProxyClass{
 		ObjectMeta: metav1.ObjectMeta{
 			Name: "default-pc",
@@ -50,6 +56,9 @@ func TestProxyGroup(t *testing.T) {
 			Name:       "test",
 			Finalizers: []string{"tailscale.com/finalizer"},
 		},
+		Spec: tsapi.ProxyGroupSpec{
+			Type: tsapi.ProxyGroupTypeEgress,
+		},
 	}
 
 	fc := fake.NewClientBuilder().
@@ -74,12 +83,21 @@ func TestProxyGroup(t *testing.T) {
 		l:        zl.Sugar(),
 		clock:    cl,
 	}
+	crd := &apiextensionsv1.CustomResourceDefinition{ObjectMeta: metav1.ObjectMeta{Name: serviceMonitorCRD}}
+	opts := configOpts{
+		proxyType:          "proxygroup",
+		stsName:            pg.Name,
+		parentType:         "proxygroup",
+		tailscaleNamespace: "tailscale",
+		resourceVersion:    "1",
+	}
 
 	t.Run("proxyclass_not_ready", func(t *testing.T) {
 		expectReconciled(t, reconciler, "", pg.Name)
 
 		tsoperator.SetProxyGroupCondition(pg, tsapi.ProxyGroupReady, metav1.ConditionFalse, reasonProxyGroupCreating, "the ProxyGroup's ProxyClass default-pc is not yet in a ready state, waiting...", 0, cl, zl.Sugar())
-		expectEqual(t, fc, pg, nil)
+		expectEqual(t, fc, pg)
+		expectProxyGroupResources(t, fc, pg, false, "")
 	})
 
 	t.Run("observe_ProxyGroupCreating_status_reason", func(t *testing.T) {
@@ -99,11 +117,12 @@ func TestProxyGroup(t *testing.T) {
 		expectReconciled(t, reconciler, "", pg.Name)
 
 		tsoperator.SetProxyGroupCondition(pg, tsapi.ProxyGroupReady, metav1.ConditionFalse, reasonProxyGroupCreating, "0/2 ProxyGroup pods running", 0, cl, zl.Sugar())
-		expectEqual(t, fc, pg, nil)
-		if expected := 1; reconciler.proxyGroups.Len() != expected {
-			t.Fatalf("expected %d recorders, got %d", expected, reconciler.proxyGroups.Len())
+		expectEqual(t, fc, pg)
+		expectProxyGroupResources(t, fc, pg, true, "")
+		if expected := 1; reconciler.egressProxyGroups.Len() != expected {
+			t.Fatalf("expected %d egress ProxyGroups, got %d", expected, reconciler.egressProxyGroups.Len())
 		}
-		expectProxyGroupResources(t, fc, pg, true)
+		expectProxyGroupResources(t, fc, pg, true, "")
 		keyReq := tailscale.KeyCapabilities{
 			Devices: tailscale.KeyDeviceCapabilities{
 				Create: tailscale.KeyDeviceCreateCapabilities{
@@ -134,8 +153,8 @@ func TestProxyGroup(t *testing.T) {
 			},
 		}
 		tsoperator.SetProxyGroupCondition(pg, tsapi.ProxyGroupReady, metav1.ConditionTrue, reasonProxyGroupReady, reasonProxyGroupReady, 0, cl, zl.Sugar())
-		expectEqual(t, fc, pg, nil)
-		expectProxyGroupResources(t, fc, pg, true)
+		expectEqual(t, fc, pg)
+		expectProxyGroupResources(t, fc, pg, true, initialCfgHash)
 	})
 
 	t.Run("scale_up_to_3", func(t *testing.T) {
@@ -145,7 +164,8 @@ func TestProxyGroup(t *testing.T) {
 		})
 		expectReconciled(t, reconciler, "", pg.Name)
 		tsoperator.SetProxyGroupCondition(pg, tsapi.ProxyGroupReady, metav1.ConditionFalse, reasonProxyGroupCreating, "2/3 ProxyGroup pods running", 0, cl, zl.Sugar())
-		expectEqual(t, fc, pg, nil)
+		expectEqual(t, fc, pg)
+		expectProxyGroupResources(t, fc, pg, true, initialCfgHash)
 
 		addNodeIDToStateSecrets(t, fc, pg)
 		expectReconciled(t, reconciler, "", pg.Name)
@@ -154,8 +174,8 @@ func TestProxyGroup(t *testing.T) {
 			Hostname:   "hostname-nodeid-2",
 			TailnetIPs: []string{"1.2.3.4", "::1"},
 		})
-		expectEqual(t, fc, pg, nil)
-		expectProxyGroupResources(t, fc, pg, true)
+		expectEqual(t, fc, pg)
+		expectProxyGroupResources(t, fc, pg, true, initialCfgHash)
 	})
 
 	t.Run("scale_down_to_1", func(t *testing.T) {
@@ -163,11 +183,47 @@ func TestProxyGroup(t *testing.T) {
 		mustUpdate(t, fc, "", pg.Name, func(p *tsapi.ProxyGroup) {
 			p.Spec = pg.Spec
 		})
-		expectReconciled(t, reconciler, "", pg.Name)
-		pg.Status.Devices = pg.Status.Devices[:1] // truncate to only the first device.
-		expectEqual(t, fc, pg, nil)
 
-		expectProxyGroupResources(t, fc, pg, true)
+		expectReconciled(t, reconciler, "", pg.Name)
+
+		pg.Status.Devices = pg.Status.Devices[:1] // truncate to only the first device.
+		expectEqual(t, fc, pg)
+		expectProxyGroupResources(t, fc, pg, true, initialCfgHash)
+	})
+
+	t.Run("trigger_config_change_and_observe_new_config_hash", func(t *testing.T) {
+		pc.Spec.TailscaleConfig = &tsapi.TailscaleConfig{
+			AcceptRoutes: true,
+		}
+		mustUpdate(t, fc, "", pc.Name, func(p *tsapi.ProxyClass) {
+			p.Spec = pc.Spec
+		})
+
+		expectReconciled(t, reconciler, "", pg.Name)
+
+		expectEqual(t, fc, pg)
+		expectProxyGroupResources(t, fc, pg, true, "518a86e9fae64f270f8e0ec2a2ea6ca06c10f725035d3d6caca132cd61e42a74")
+	})
+
+	t.Run("enable_metrics", func(t *testing.T) {
+		pc.Spec.Metrics = &tsapi.Metrics{Enable: true}
+		mustUpdate(t, fc, "", pc.Name, func(p *tsapi.ProxyClass) {
+			p.Spec = pc.Spec
+		})
+		expectReconciled(t, reconciler, "", pg.Name)
+		expectEqual(t, fc, expectedMetricsService(opts))
+	})
+	t.Run("enable_service_monitor_no_crd", func(t *testing.T) {
+		pc.Spec.Metrics.ServiceMonitor = &tsapi.ServiceMonitor{Enable: true}
+		mustUpdate(t, fc, "", pc.Name, func(p *tsapi.ProxyClass) {
+			p.Spec.Metrics = pc.Spec.Metrics
+		})
+		expectReconciled(t, reconciler, "", pg.Name)
+	})
+	t.Run("create_crd_expect_service_monitor", func(t *testing.T) {
+		mustCreate(t, fc, crd)
+		expectReconciled(t, reconciler, "", pg.Name)
+		expectEqualUnstructured(t, fc, expectedServiceMonitor(t, opts))
 	})
 
 	t.Run("delete_and_cleanup", func(t *testing.T) {
@@ -177,39 +233,195 @@ func TestProxyGroup(t *testing.T) {
 
 		expectReconciled(t, reconciler, "", pg.Name)
 
-		expectMissing[tsapi.Recorder](t, fc, "", pg.Name)
-		if expected := 0; reconciler.proxyGroups.Len() != expected {
-			t.Fatalf("expected %d ProxyGroups, got %d", expected, reconciler.proxyGroups.Len())
+		expectMissing[tsapi.ProxyGroup](t, fc, "", pg.Name)
+		if expected := 0; reconciler.egressProxyGroups.Len() != expected {
+			t.Fatalf("expected %d ProxyGroups, got %d", expected, reconciler.egressProxyGroups.Len())
 		}
 		// 2 nodes should get deleted as part of the scale down, and then finally
 		// the first node gets deleted with the ProxyGroup cleanup.
 		if diff := cmp.Diff(tsClient.deleted, []string{"nodeid-1", "nodeid-2", "nodeid-0"}); diff != "" {
 			t.Fatalf("unexpected deleted devices (-got +want):\n%s", diff)
 		}
+		expectMissing[corev1.Service](t, reconciler, "tailscale", metricsResourceName(pg.Name))
 		// The fake client does not clean up objects whose owner has been
 		// deleted, so we can't test for the owned resources getting deleted.
 	})
 }
 
-func expectProxyGroupResources(t *testing.T, fc client.WithWatch, pg *tsapi.ProxyGroup, shouldExist bool) {
+func TestProxyGroupTypes(t *testing.T) {
+	fc := fake.NewClientBuilder().
+		WithScheme(tsapi.GlobalScheme).
+		Build()
+
+	zl, _ := zap.NewDevelopment()
+	reconciler := &ProxyGroupReconciler{
+		tsNamespace: tsNamespace,
+		proxyImage:  testProxyImage,
+		Client:      fc,
+		l:           zl.Sugar(),
+		tsClient:    &fakeTSClient{},
+		clock:       tstest.NewClock(tstest.ClockOpts{}),
+	}
+
+	t.Run("egress_type", func(t *testing.T) {
+		pg := &tsapi.ProxyGroup{
+			ObjectMeta: metav1.ObjectMeta{
+				Name: "test-egress",
+				UID:  "test-egress-uid",
+			},
+			Spec: tsapi.ProxyGroupSpec{
+				Type:     tsapi.ProxyGroupTypeEgress,
+				Replicas: ptr.To[int32](0),
+			},
+		}
+		if err := fc.Create(context.Background(), pg); err != nil {
+			t.Fatal(err)
+		}
+
+		expectReconciled(t, reconciler, "", pg.Name)
+		verifyProxyGroupCounts(t, reconciler, 0, 1)
+
+		sts := &appsv1.StatefulSet{}
+		if err := fc.Get(context.Background(), client.ObjectKey{Namespace: tsNamespace, Name: pg.Name}, sts); err != nil {
+			t.Fatalf("failed to get StatefulSet: %v", err)
+		}
+		verifyEnvVar(t, sts, "TS_INTERNAL_APP", kubetypes.AppProxyGroupEgress)
+		verifyEnvVar(t, sts, "TS_EGRESS_SERVICES_CONFIG_PATH", fmt.Sprintf("/etc/proxies/%s", egressservices.KeyEgressServices))
+
+		// Verify that egress configuration has been set up.
+		cm := &corev1.ConfigMap{}
+		cmName := fmt.Sprintf("%s-egress-config", pg.Name)
+		if err := fc.Get(context.Background(), client.ObjectKey{Namespace: tsNamespace, Name: cmName}, cm); err != nil {
+			t.Fatalf("failed to get ConfigMap: %v", err)
+		}
+
+		expectedVolumes := []corev1.Volume{
+			{
+				Name: cmName,
+				VolumeSource: corev1.VolumeSource{
+					ConfigMap: &corev1.ConfigMapVolumeSource{
+						LocalObjectReference: corev1.LocalObjectReference{
+							Name: cmName,
+						},
+					},
+				},
+			},
+		}
+
+		expectedVolumeMounts := []corev1.VolumeMount{
+			{
+				Name:      cmName,
+				MountPath: "/etc/proxies",
+				ReadOnly:  true,
+			},
+		}
+
+		if diff := cmp.Diff(expectedVolumes, sts.Spec.Template.Spec.Volumes); diff != "" {
+			t.Errorf("unexpected volumes (-want +got):\n%s", diff)
+		}
+
+		if diff := cmp.Diff(expectedVolumeMounts, sts.Spec.Template.Spec.Containers[0].VolumeMounts); diff != "" {
+			t.Errorf("unexpected volume mounts (-want +got):\n%s", diff)
+		}
+	})
+
+	t.Run("ingress_type", func(t *testing.T) {
+		pg := &tsapi.ProxyGroup{
+			ObjectMeta: metav1.ObjectMeta{
+				Name: "test-ingress",
+				UID:  "test-ingress-uid",
+			},
+			Spec: tsapi.ProxyGroupSpec{
+				Type:     tsapi.ProxyGroupTypeIngress,
+				Replicas: ptr.To[int32](0),
+			},
+		}
+		if err := fc.Create(context.Background(), pg); err != nil {
+			t.Fatal(err)
+		}
+
+		expectReconciled(t, reconciler, "", pg.Name)
+		verifyProxyGroupCounts(t, reconciler, 1, 1)
+
+		sts := &appsv1.StatefulSet{}
+		if err := fc.Get(context.Background(), client.ObjectKey{Namespace: tsNamespace, Name: pg.Name}, sts); err != nil {
+			t.Fatalf("failed to get StatefulSet: %v", err)
+		}
+		verifyEnvVar(t, sts, "TS_INTERNAL_APP", kubetypes.AppProxyGroupIngress)
+		verifyEnvVar(t, sts, "TS_SERVE_CONFIG", "/etc/proxies/serve-config.json")
+
+		// Verify ConfigMap volume mount
+		cmName := fmt.Sprintf("%s-ingress-config", pg.Name)
+		expectedVolume := corev1.Volume{
+			Name: cmName,
+			VolumeSource: corev1.VolumeSource{
+				ConfigMap: &corev1.ConfigMapVolumeSource{
+					LocalObjectReference: corev1.LocalObjectReference{
+						Name: cmName,
+					},
+				},
+			},
+		}
+
+		expectedVolumeMount := corev1.VolumeMount{
+			Name:      cmName,
+			MountPath: "/etc/proxies",
+			ReadOnly:  true,
+		}
+
+		if diff := cmp.Diff([]corev1.Volume{expectedVolume}, sts.Spec.Template.Spec.Volumes); diff != "" {
+			t.Errorf("unexpected volumes (-want +got):\n%s", diff)
+		}
+
+		if diff := cmp.Diff([]corev1.VolumeMount{expectedVolumeMount}, sts.Spec.Template.Spec.Containers[0].VolumeMounts); diff != "" {
+			t.Errorf("unexpected volume mounts (-want +got):\n%s", diff)
+		}
+	})
+}
+
+func verifyProxyGroupCounts(t *testing.T, r *ProxyGroupReconciler, wantIngress, wantEgress int) {
+	t.Helper()
+	if r.ingressProxyGroups.Len() != wantIngress {
+		t.Errorf("expected %d ingress proxy groups, got %d", wantIngress, r.ingressProxyGroups.Len())
+	}
+	if r.egressProxyGroups.Len() != wantEgress {
+		t.Errorf("expected %d egress proxy groups, got %d", wantEgress, r.egressProxyGroups.Len())
+	}
+}
+
+func verifyEnvVar(t *testing.T, sts *appsv1.StatefulSet, name, expectedValue string) {
+	t.Helper()
+	for _, env := range sts.Spec.Template.Spec.Containers[0].Env {
+		if env.Name == name {
+			if env.Value != expectedValue {
+				t.Errorf("expected %s=%s, got %s", name, expectedValue, env.Value)
+			}
+			return
+		}
+	}
+	t.Errorf("%s environment variable not found", name)
+}
+
+func expectProxyGroupResources(t *testing.T, fc client.WithWatch, pg *tsapi.ProxyGroup, shouldExist bool, cfgHash string) {
 	t.Helper()
 
 	role := pgRole(pg, tsNamespace)
 	roleBinding := pgRoleBinding(pg, tsNamespace)
 	serviceAccount := pgServiceAccount(pg, tsNamespace)
-	statefulSet, err := pgStatefulSet(pg, tsNamespace, testProxyImage, "auto", "")
+	statefulSet, err := pgStatefulSet(pg, tsNamespace, testProxyImage, "auto")
 	if err != nil {
 		t.Fatal(err)
 	}
 	statefulSet.Annotations = defaultProxyClassAnnotations
+	if cfgHash != "" {
+		mak.Set(&statefulSet.Spec.Template.Annotations, podAnnotationLastSetConfigFileHash, cfgHash)
+	}
 
 	if shouldExist {
-		expectEqual(t, fc, role, nil)
-		expectEqual(t, fc, roleBinding, nil)
-		expectEqual(t, fc, serviceAccount, nil)
-		expectEqual(t, fc, statefulSet, func(ss *appsv1.StatefulSet) {
-			ss.Spec.Template.Annotations[podAnnotationLastSetConfigFileHash] = ""
-		})
+		expectEqual(t, fc, role)
+		expectEqual(t, fc, roleBinding)
+		expectEqual(t, fc, serviceAccount)
+		expectEqual(t, fc, statefulSet, removeResourceReqs)
 	} else {
 		expectMissing[rbacv1.Role](t, fc, role.Namespace, role.Name)
 		expectMissing[rbacv1.RoleBinding](t, fc, roleBinding.Namespace, roleBinding.Name)
@@ -218,11 +430,13 @@ func expectProxyGroupResources(t *testing.T, fc client.WithWatch, pg *tsapi.Prox
 	}
 
 	var expectedSecrets []string
-	for i := range pgReplicas(pg) {
-		expectedSecrets = append(expectedSecrets,
-			fmt.Sprintf("%s-%d", pg.Name, i),
-			fmt.Sprintf("%s-%d-config", pg.Name, i),
-		)
+	if shouldExist {
+		for i := range pgReplicas(pg) {
+			expectedSecrets = append(expectedSecrets,
+				fmt.Sprintf("%s-%d", pg.Name, i),
+				fmt.Sprintf("%s-%d-config", pg.Name, i),
+			)
+		}
 	}
 	expectSecrets(t, fc, expectedSecrets)
 }

cmd/k8s-operator/sts.go

@@ -15,6 +15,7 @@ import (
 	"net/http"
 	"os"
 	"slices"
+	"strconv"
 	"strings"
 
 	"go.uber.org/zap"
@@ -94,6 +95,12 @@ const (
 	podAnnotationLastSetTailnetTargetFQDN = "tailscale.com/operator-last-set-ts-tailnet-target-fqdn"
 	// podAnnotationLastSetConfigFileHash is sha256 hash of the current tailscaled configuration contents.
 	podAnnotationLastSetConfigFileHash = "tailscale.com/operator-last-set-config-file-hash"
+
+	proxyTypeEgress          = "egress_service"
+	proxyTypeIngressService  = "ingress_service"
+	proxyTypeIngressResource = "ingress_resource"
+	proxyTypeConnector       = "connector"
+	proxyTypeProxyGroup      = "proxygroup"
 )
 
 var (
@@ -122,6 +129,8 @@ type tailscaleSTSConfig struct {
 	Hostname string
 	Tags     []string // if empty, use defaultTags
 
+	proxyType string
+
 	// Connector specifies a configuration of a Connector instance if that's
 	// what this StatefulSet should be created for.
 	Connector *connector
@@ -132,10 +141,13 @@ type tailscaleSTSConfig struct {
 }
 
 type connector struct {
-	// routes is a list of subnet routes that this Connector should expose.
+	// routes is a list of routes that this Connector should advertise either as a subnet router or as an app
+	// connector.
 	routes string
 	// isExitNode defines whether this Connector should act as an exit node.
 	isExitNode bool
+	// isAppConnector defines whether this Connector should act as an app connector.
+	isAppConnector bool
 }
 type tsnetServer interface {
 	CertDomains() []string
@@ -160,8 +172,8 @@ func (sts tailscaleSTSReconciler) validate() error {
 }
 
 // IsHTTPSEnabledOnTailnet reports whether HTTPS is enabled on the tailnet.
-func (a *tailscaleSTSReconciler) IsHTTPSEnabledOnTailnet() bool {
-	return len(a.tsnetServer.CertDomains()) > 0
+func IsHTTPSEnabledOnTailnet(tsnetServer tsnetServer) bool {
+	return len(tsnetServer.CertDomains()) > 0
 }
 
 // Provision ensures that the StatefulSet for the given service is running and
@@ -186,22 +198,30 @@ func (a *tailscaleSTSReconciler) Provision(ctx context.Context, logger *zap.Suga
 	}
 	sts.ProxyClass = proxyClass
 
-	secretName, tsConfigHash, configs, err := a.createOrGetSecret(ctx, logger, sts, hsvc)
+	secretName, tsConfigHash, _, err := a.createOrGetSecret(ctx, logger, sts, hsvc)
 	if err != nil {
 		return nil, fmt.Errorf("failed to create or get API key secret: %w", err)
 	}
-	_, err = a.reconcileSTS(ctx, logger, sts, hsvc, secretName, tsConfigHash, configs)
+	_, err = a.reconcileSTS(ctx, logger, sts, hsvc, secretName, tsConfigHash)
 	if err != nil {
 		return nil, fmt.Errorf("failed to reconcile statefulset: %w", err)
 	}
-
+	mo := &metricsOpts{
+		proxyStsName: hsvc.Name,
+		tsNamespace:  hsvc.Namespace,
+		proxyLabels:  hsvc.Labels,
+		proxyType:    sts.proxyType,
+	}
+	if err = reconcileMetricsResources(ctx, logger, mo, sts.ProxyClass, a.Client); err != nil {
+		return nil, fmt.Errorf("failed to ensure metrics resources: %w", err)
+	}
 	return hsvc, nil
 }
 
 // Cleanup removes all resources associated that were created by Provision with
 // the given labels. It returns true when all resources have been removed,
 // otherwise it returns false and the caller should retry later.
-func (a *tailscaleSTSReconciler) Cleanup(ctx context.Context, logger *zap.SugaredLogger, labels map[string]string) (done bool, _ error) {
+func (a *tailscaleSTSReconciler) Cleanup(ctx context.Context, logger *zap.SugaredLogger, labels map[string]string, typ string) (done bool, _ error) {
 	// Need to delete the StatefulSet first, and delete it with foreground
 	// cascading deletion. That way, the pod that's writing to the Secret will
 	// stop running before we start looking at the Secret's contents, and
@@ -227,21 +247,21 @@ func (a *tailscaleSTSReconciler) Cleanup(ctx context.Context, logger *zap.Sugare
 		return false, nil
 	}
 
-	id, _, _, err := a.DeviceInfo(ctx, labels)
+	dev, err := a.DeviceInfo(ctx, labels, logger)
 	if err != nil {
 		return false, fmt.Errorf("getting device info: %w", err)
 	}
-	if id != "" {
-		logger.Debugf("deleting device %s from control", string(id))
-		if err := a.tsClient.DeleteDevice(ctx, string(id)); err != nil {
+	if dev != nil && dev.id != "" {
+		logger.Debugf("deleting device %s from control", string(dev.id))
+		if err := a.tsClient.DeleteDevice(ctx, string(dev.id)); err != nil {
 			errResp := &tailscale.ErrResponse{}
 			if ok := errors.As(err, errResp); ok && errResp.Status == http.StatusNotFound {
-				logger.Debugf("device %s not found, likely because it has already been deleted from control", string(id))
+				logger.Debugf("device %s not found, likely because it has already been deleted from control", string(dev.id))
 			} else {
 				return false, fmt.Errorf("deleting device: %w", err)
 			}
 		} else {
-			logger.Debugf("device %s deleted from control", string(id))
+			logger.Debugf("device %s deleted from control", string(dev.id))
 		}
 	}
 
@@ -254,6 +274,14 @@ func (a *tailscaleSTSReconciler) Cleanup(ctx context.Context, logger *zap.Sugare
 			return false, err
 		}
 	}
+	mo := &metricsOpts{
+		proxyLabels: labels,
+		tsNamespace: a.operatorNamespace,
+		proxyType:   typ,
+	}
+	if err := maybeCleanupMetricsResources(ctx, mo, a.Client); err != nil {
+		return false, fmt.Errorf("error cleaning up metrics resources: %w", err)
+	}
 	return true, nil
 }
 
@@ -409,44 +437,75 @@ func sanitizeConfigBytes(c ipn.ConfigVAlpha) string {
 	return string(sanitizedBytes)
 }
 
-// DeviceInfo returns the device ID, hostname and IPs for the Tailscale device
-// that acts as an operator proxy. It retrieves info from a Kubernetes Secret
-// labeled with the provided labels.
-// Either of device ID, hostname and IPs can be empty string if not found in the Secret.
-func (a *tailscaleSTSReconciler) DeviceInfo(ctx context.Context, childLabels map[string]string) (id tailcfg.StableNodeID, hostname string, ips []string, err error) {
+// DeviceInfo returns the device ID, hostname, IPs and capver for the Tailscale device that acts as an operator proxy.
+// It retrieves info from a Kubernetes Secret labeled with the provided labels. Capver is cross-validated against the
+// Pod to ensure that it is the currently running Pod that set the capver. If the Pod or the Secret does not exist, the
+// returned capver is -1. Either of device ID, hostname and IPs can be empty string if not found in the Secret.
+func (a *tailscaleSTSReconciler) DeviceInfo(ctx context.Context, childLabels map[string]string, logger *zap.SugaredLogger) (dev *device, err error) {
 	sec, err := getSingleObject[corev1.Secret](ctx, a.Client, a.operatorNamespace, childLabels)
 	if err != nil {
-		return "", "", nil, err
+		return dev, err
 	}
 	if sec == nil {
-		return "", "", nil, nil
+		return dev, nil
 	}
-
-	return deviceInfo(sec)
+	podUID := ""
+	pod := new(corev1.Pod)
+	if err := a.Get(ctx, types.NamespacedName{Namespace: sec.Namespace, Name: sec.Name}, pod); err != nil && !apierrors.IsNotFound(err) {
+		return dev, err
+	} else if err == nil {
+		podUID = string(pod.ObjectMeta.UID)
+	}
+	return deviceInfo(sec, podUID, logger)
 }
 
-func deviceInfo(sec *corev1.Secret) (id tailcfg.StableNodeID, hostname string, ips []string, err error) {
-	id = tailcfg.StableNodeID(sec.Data["device_id"])
+// device contains tailscale state of a proxy device as gathered from its tailscale state Secret.
+type device struct {
+	id       tailcfg.StableNodeID // device's stable ID
+	hostname string               // MagicDNS name of the device
+	ips      []string             // Tailscale IPs of the device
+	// ingressDNSName is the L7 Ingress DNS name. In practice this will be the same value as hostname, but only set
+	// when the device has been configured to serve traffic on it via 'tailscale serve'.
+	ingressDNSName string
+	capver         tailcfg.CapabilityVersion
+}
+
+func deviceInfo(sec *corev1.Secret, podUID string, log *zap.SugaredLogger) (dev *device, err error) {
+	id := tailcfg.StableNodeID(sec.Data[kubetypes.KeyDeviceID])
 	if id == "" {
-		return "", "", nil, nil
+		return dev, nil
 	}
+	dev = &device{id: id}
 	// Kubernetes chokes on well-formed FQDNs with the trailing dot, so we have
 	// to remove it.
-	hostname = strings.TrimSuffix(string(sec.Data["device_fqdn"]), ".")
-	if hostname == "" {
+	dev.hostname = strings.TrimSuffix(string(sec.Data[kubetypes.KeyDeviceFQDN]), ".")
+	if dev.hostname == "" {
 		// Device ID gets stored and retrieved in a different flow than
 		// FQDN and IPs. A device that acts as Kubernetes operator
-		// proxy, but whose route setup has failed might have an device
+		// proxy, but whose route setup has failed might have a device
 		// ID, but no FQDN/IPs. If so, return the ID, to allow the
 		// operator to clean up such devices.
-		return id, "", nil, nil
+		return dev, nil
 	}
-	if rawDeviceIPs, ok := sec.Data["device_ips"]; ok {
-		if err := json.Unmarshal(rawDeviceIPs, &ips); err != nil {
-			return "", "", nil, err
+	dev.ingressDNSName = dev.hostname
+	pcv := proxyCapVer(sec, podUID, log)
+	dev.capver = pcv
+	// TODO(irbekrm): we fall back to using the hostname field to determine Ingress's hostname to ensure backwards
+	// compatibility. In 1.82 we can remove this fallback mechanism.
+	if pcv >= 109 {
+		dev.ingressDNSName = strings.TrimSuffix(string(sec.Data[kubetypes.KeyHTTPSEndpoint]), ".")
+		if strings.EqualFold(dev.ingressDNSName, kubetypes.ValueNoHTTPS) {
+			dev.ingressDNSName = ""
 		}
 	}
-	return id, hostname, ips, nil
+	if rawDeviceIPs, ok := sec.Data[kubetypes.KeyDeviceIPs]; ok {
+		ips := make([]string, 0)
+		if err := json.Unmarshal(rawDeviceIPs, &ips); err != nil {
+			return nil, err
+		}
+		dev.ips = ips
+	}
+	return dev, nil
 }
 
 func newAuthKey(ctx context.Context, tsClient tsClient, tags []string) (string, error) {
@@ -473,7 +532,7 @@ var proxyYaml []byte
 //go:embed deploy/manifests/userspace-proxy.yaml
 var userspaceProxyYaml []byte
 
-func (a *tailscaleSTSReconciler) reconcileSTS(ctx context.Context, logger *zap.SugaredLogger, sts *tailscaleSTSConfig, headlessSvc *corev1.Service, proxySecret, tsConfigHash string, configs map[tailcfg.CapabilityVersion]ipn.ConfigVAlpha) (*appsv1.StatefulSet, error) {
+func (a *tailscaleSTSReconciler) reconcileSTS(ctx context.Context, logger *zap.SugaredLogger, sts *tailscaleSTSConfig, headlessSvc *corev1.Service, proxySecret, tsConfigHash string) (*appsv1.StatefulSet, error) {
 	ss := new(appsv1.StatefulSet)
 	if sts.ServeConfig != nil && sts.ForwardClusterTrafficViaL7IngressProxy != true { // If forwarding cluster traffic via is required we need non-userspace + NET_ADMIN + forwarding
 		if err := yaml.Unmarshal(userspaceProxyYaml, &ss); err != nil {
@@ -518,11 +577,6 @@ func (a *tailscaleSTSReconciler) reconcileSTS(ctx context.Context, logger *zap.S
 			Name:  "TS_KUBE_SECRET",
 			Value: proxySecret,
 		},
-		corev1.EnvVar{
-			// Old tailscaled config key is still used for backwards compatibility.
-			Name:  "EXPERIMENTAL_TS_CONFIGFILE_PATH",
-			Value: "/etc/tsconfig/tailscaled",
-		},
 		corev1.EnvVar{
 			// New style is in the form of cap-<capability-version>.hujson.
 			Name:  "TS_EXPERIMENTAL_VERSIONED_CONFIG_DIR",
@@ -535,8 +589,6 @@ func (a *tailscaleSTSReconciler) reconcileSTS(ctx context.Context, logger *zap.S
 			Value: "true",
 		})
 	}
-	// Configure containeboot to run tailscaled with a configfile read from the state Secret.
-	mak.Set(&ss.Spec.Template.Annotations, podAnnotationLastSetConfigFileHash, tsConfigHash)
 
 	configVolume := corev1.Volume{
 		Name: "tailscaledconfig",
@@ -606,6 +658,12 @@ func (a *tailscaleSTSReconciler) reconcileSTS(ctx context.Context, logger *zap.S
 			},
 		})
 	}
+
+	dev, err := a.DeviceInfo(ctx, sts.ChildResourceLabels, logger)
+	if err != nil {
+		return nil, fmt.Errorf("failed to get device info: %w", err)
+	}
+
 	app, err := appInfoForProxy(sts)
 	if err != nil {
 		// No need to error out if now or in future we end up in a
@@ -624,7 +682,25 @@ func (a *tailscaleSTSReconciler) reconcileSTS(ctx context.Context, logger *zap.S
 		ss = applyProxyClassToStatefulSet(sts.ProxyClass, ss, sts, logger)
 	}
 	updateSS := func(s *appsv1.StatefulSet) {
+		// This is a temporary workaround to ensure that proxies with capver older than 110
+		// are restarted when tailscaled configfile contents have changed.
+		// This workaround ensures that:
+		// 1. The hash mechanism is used to trigger pod restarts for proxies below capver 110.
+		// 2. Proxies above capver are not unnecessarily restarted when the configfile contents change.
+		// 3. If the hash has alreay been set, but the capver is above 110, the old hash is preserved to avoid
+		// unnecessary pod restarts that could result in an update loop where capver cannot be determined for a
+		// restarting Pod and the hash is re-added again.
+		// Note that the hash annotation is only set on updates not creation, because if the StatefulSet is
+		// being created, there is no need for a restart.
+		// TODO(irbekrm): remove this in 1.84.
+		hash := tsConfigHash
+		if dev != nil && dev.capver >= 110 {
+			hash = s.Spec.Template.GetAnnotations()[podAnnotationLastSetConfigFileHash]
+		}
 		s.Spec = ss.Spec
+		if hash != "" {
+			mak.Set(&s.Spec.Template.Annotations, podAnnotationLastSetConfigFileHash, hash)
+		}
 		s.ObjectMeta.Labels = ss.Labels
 		s.ObjectMeta.Annotations = ss.Annotations
 	}
@@ -668,24 +744,42 @@ func mergeStatefulSetLabelsOrAnnots(current, custom map[string]string, managed [
 	return custom
 }
 
+func debugSetting(pc *tsapi.ProxyClass) bool {
+	if pc == nil ||
+		pc.Spec.StatefulSet == nil ||
+		pc.Spec.StatefulSet.Pod == nil ||
+		pc.Spec.StatefulSet.Pod.TailscaleContainer == nil ||
+		pc.Spec.StatefulSet.Pod.TailscaleContainer.Debug == nil {
+		// This default will change to false in 1.82.0.
+		return pc.Spec.Metrics != nil && pc.Spec.Metrics.Enable
+	}
+
+	return pc.Spec.StatefulSet.Pod.TailscaleContainer.Debug.Enable
+}
+
 func applyProxyClassToStatefulSet(pc *tsapi.ProxyClass, ss *appsv1.StatefulSet, stsCfg *tailscaleSTSConfig, logger *zap.SugaredLogger) *appsv1.StatefulSet {
 	if pc == nil || ss == nil {
 		return ss
 	}
-	if stsCfg != nil && pc.Spec.Metrics != nil && pc.Spec.Metrics.Enable {
-		if stsCfg.TailnetTargetFQDN == "" && stsCfg.TailnetTargetIP == "" && !stsCfg.ForwardClusterTrafficViaL7IngressProxy {
-			enableMetrics(ss, pc)
-		} else if stsCfg.ForwardClusterTrafficViaL7IngressProxy {
+
+	metricsEnabled := pc.Spec.Metrics != nil && pc.Spec.Metrics.Enable
+	debugEnabled := debugSetting(pc)
+	if metricsEnabled || debugEnabled {
+		isEgress := stsCfg != nil && (stsCfg.TailnetTargetFQDN != "" || stsCfg.TailnetTargetIP != "")
+		isForwardingL7Ingress := stsCfg != nil && stsCfg.ForwardClusterTrafficViaL7IngressProxy
+		if isEgress {
 			// TODO (irbekrm): fix this
 			// For Ingress proxies that have been configured with
 			// tailscale.com/experimental-forward-cluster-traffic-via-ingress
 			// annotation, all cluster traffic is forwarded to the
 			// Ingress backend(s).
-			logger.Info("ProxyClass specifies that metrics should be enabled, but this is currently not supported for Ingress proxies that accept cluster traffic.")
-		} else {
+			logger.Info("ProxyClass specifies that metrics should be enabled, but this is currently not supported for egress proxies.")
+		} else if isForwardingL7Ingress {
 			// TODO (irbekrm): fix this
 			// For egress proxies, currently all cluster traffic is forwarded to the tailnet target.
 			logger.Info("ProxyClass specifies that metrics should be enabled, but this is currently not supported for Ingress proxies that accept cluster traffic.")
+		} else {
+			enableEndpoints(ss, metricsEnabled, debugEnabled)
 		}
 	}
 
@@ -694,7 +788,7 @@ func applyProxyClassToStatefulSet(pc *tsapi.ProxyClass, ss *appsv1.StatefulSet,
 	}
 
 	// Update StatefulSet metadata.
-	if wantsSSLabels := pc.Spec.StatefulSet.Labels; len(wantsSSLabels) > 0 {
+	if wantsSSLabels := pc.Spec.StatefulSet.Labels.Parse(); len(wantsSSLabels) > 0 {
 		ss.ObjectMeta.Labels = mergeStatefulSetLabelsOrAnnots(ss.ObjectMeta.Labels, wantsSSLabels, tailscaleManagedLabels)
 	}
 	if wantsSSAnnots := pc.Spec.StatefulSet.Annotations; len(wantsSSAnnots) > 0 {
@@ -706,7 +800,7 @@ func applyProxyClassToStatefulSet(pc *tsapi.ProxyClass, ss *appsv1.StatefulSet,
 		return ss
 	}
 	wantsPod := pc.Spec.StatefulSet.Pod
-	if wantsPodLabels := wantsPod.Labels; len(wantsPodLabels) > 0 {
+	if wantsPodLabels := wantsPod.Labels.Parse(); len(wantsPodLabels) > 0 {
 		ss.Spec.Template.ObjectMeta.Labels = mergeStatefulSetLabelsOrAnnots(ss.Spec.Template.ObjectMeta.Labels, wantsPodLabels, tailscaleManagedLabels)
 	}
 	if wantsPodAnnots := wantsPod.Annotations; len(wantsPodAnnots) > 0 {
@@ -763,16 +857,58 @@ func applyProxyClassToStatefulSet(pc *tsapi.ProxyClass, ss *appsv1.StatefulSet,
 	return ss
 }
 
-func enableMetrics(ss *appsv1.StatefulSet, pc *tsapi.ProxyClass) {
+func enableEndpoints(ss *appsv1.StatefulSet, metrics, debug bool) {
 	for i, c := range ss.Spec.Template.Spec.Containers {
 		if c.Name == "tailscale" {
-			// Serve metrics on on <pod-ip>:9001/debug/metrics. If
-			// we didn't specify Pod IP here, the proxy would, in
-			// some cases, also listen to its Tailscale IP- we don't
-			// want folks to start relying on this side-effect as a
-			// feature.
-			ss.Spec.Template.Spec.Containers[i].Env = append(ss.Spec.Template.Spec.Containers[i].Env, corev1.EnvVar{Name: "TS_TAILSCALED_EXTRA_ARGS", Value: "--debug=$(POD_IP):9001"})
-			ss.Spec.Template.Spec.Containers[i].Ports = append(ss.Spec.Template.Spec.Containers[i].Ports, corev1.ContainerPort{Name: "metrics", Protocol: "TCP", HostPort: 9001, ContainerPort: 9001})
+			if debug {
+				ss.Spec.Template.Spec.Containers[i].Env = append(ss.Spec.Template.Spec.Containers[i].Env,
+					// Serve tailscaled's debug metrics on on
+					// <pod-ip>:9001/debug/metrics. If we didn't specify Pod IP
+					// here, the proxy would, in some cases, also listen to its
+					// Tailscale IP- we don't want folks to start relying on this
+					// side-effect as a feature.
+					corev1.EnvVar{
+						Name:  "TS_DEBUG_ADDR_PORT",
+						Value: "$(POD_IP):9001",
+					},
+					// TODO(tomhjp): Can remove this env var once 1.76.x is no
+					// longer supported.
+					corev1.EnvVar{
+						Name:  "TS_TAILSCALED_EXTRA_ARGS",
+						Value: "--debug=$(TS_DEBUG_ADDR_PORT)",
+					},
+				)
+
+				ss.Spec.Template.Spec.Containers[i].Ports = append(ss.Spec.Template.Spec.Containers[i].Ports,
+					corev1.ContainerPort{
+						Name:          "debug",
+						Protocol:      "TCP",
+						ContainerPort: 9001,
+					},
+				)
+			}
+
+			if metrics {
+				ss.Spec.Template.Spec.Containers[i].Env = append(ss.Spec.Template.Spec.Containers[i].Env,
+					// Serve client metrics on <pod-ip>:9002/metrics.
+					corev1.EnvVar{
+						Name:  "TS_LOCAL_ADDR_PORT",
+						Value: "$(POD_IP):9002",
+					},
+					corev1.EnvVar{
+						Name:  "TS_ENABLE_METRICS",
+						Value: "true",
+					},
+				)
+				ss.Spec.Template.Spec.Containers[i].Ports = append(ss.Spec.Template.Spec.Containers[i].Ports,
+					corev1.ContainerPort{
+						Name:          "metrics",
+						Protocol:      "TCP",
+						ContainerPort: 9002,
+					},
+				)
+			}
+
 			break
 		}
 	}
@@ -786,15 +922,9 @@ func readAuthKey(secret *corev1.Secret, key string) (*string, error) {
 	return origConf.AuthKey, nil
 }
 
-// tailscaledConfig takes a proxy config, a newly generated auth key if
-// generated and a Secret with the previous proxy state and auth key and
-// returns tailscaled configuration and a hash of that configuration.
-//
-// As of 2024-05-09 it also returns legacy tailscaled config without the
-// later added NoStatefulFilter field to support proxies older than cap95.
-// TODO (irbekrm): remove the legacy config once we no longer need to support
-// versions older than cap94,
-// https://tailscale.com/kb/1236/kubernetes-operator#operator-and-proxies
+// tailscaledConfig takes a proxy config, a newly generated auth key if generated and a Secret with the previous proxy
+// state and auth key and returns tailscaled config files for currently supported proxy versions and a hash of that
+// configuration.
 func tailscaledConfig(stsC *tailscaleSTSConfig, newAuthkey string, oldSecret *corev1.Secret) (tailscaledConfigs, error) {
 	conf := &ipn.ConfigVAlpha{
 		Version:             "alpha0",
@@ -802,21 +932,19 @@ func tailscaledConfig(stsC *tailscaleSTSConfig, newAuthkey string, oldSecret *co
 		AcceptRoutes:        "false", // AcceptRoutes defaults to true
 		Locked:              "false",
 		Hostname:            &stsC.Hostname,
-		NoStatefulFiltering: "false",
+		NoStatefulFiltering: "true", // Explicitly enforce default value, see #14216
+		AppConnector:        &ipn.AppConnectorPrefs{Advertise: false},
 	}
 
-	// For egress proxies only, we need to ensure that stateful filtering is
-	// not in place so that traffic from cluster can be forwarded via
-	// Tailscale IPs.
-	if stsC.TailnetTargetFQDN != "" || stsC.TailnetTargetIP != "" {
-		conf.NoStatefulFiltering = "true"
-	}
 	if stsC.Connector != nil {
 		routes, err := netutil.CalcAdvertiseRoutes(stsC.Connector.routes, stsC.Connector.isExitNode)
 		if err != nil {
 			return nil, fmt.Errorf("error calculating routes: %w", err)
 		}
 		conf.AdvertiseRoutes = routes
+		if stsC.Connector.isAppConnector {
+			conf.AppConnector.Advertise = true
+		}
 	}
 	if shouldAcceptRoutes(stsC.ProxyClass) {
 		conf.AcceptRoutes = "true"
@@ -831,11 +959,13 @@ func tailscaledConfig(stsC *tailscaleSTSConfig, newAuthkey string, oldSecret *co
 		}
 		conf.AuthKey = key
 	}
+
 	capVerConfigs := make(map[tailcfg.CapabilityVersion]ipn.ConfigVAlpha)
+	capVerConfigs[107] = *conf
+
+	// AppConnector config option is only understood by clients of capver 107 and newer.
+	conf.AppConnector = nil
 	capVerConfigs[95] = *conf
-	// legacy config should not contain NoStatefulFiltering field.
-	conf.NoStatefulFiltering.Clear()
-	capVerConfigs[94] = *conf
 	return capVerConfigs, nil
 }
 
@@ -1008,3 +1138,24 @@ func nameForService(svc *corev1.Service) string {
 func isValidFirewallMode(m string) bool {
 	return m == "auto" || m == "nftables" || m == "iptables"
 }
+
+// proxyCapVer accepts a proxy state Secret and UID of the current proxy Pod returns the capability version of the
+// tailscale running in that Pod. This is best effort - if the capability version can not (currently) be determined, it
+// returns -1.
+func proxyCapVer(sec *corev1.Secret, podUID string, log *zap.SugaredLogger) tailcfg.CapabilityVersion {
+	if sec == nil || podUID == "" {
+		return tailcfg.CapabilityVersion(-1)
+	}
+	if len(sec.Data[kubetypes.KeyCapVer]) == 0 || len(sec.Data[kubetypes.KeyPodUID]) == 0 {
+		return tailcfg.CapabilityVersion(-1)
+	}
+	capVer, err := strconv.Atoi(string(sec.Data[kubetypes.KeyCapVer]))
+	if err != nil {
+		log.Infof("[unexpected]: unexpected capability version in proxy's state Secret, expected an integer, got %q", string(sec.Data[kubetypes.KeyCapVer]))
+		return tailcfg.CapabilityVersion(-1)
+	}
+	if !strings.EqualFold(podUID, string(sec.Data[kubetypes.KeyPodUID])) {
+		return tailcfg.CapabilityVersion(-1)
+	}
+	return tailcfg.CapabilityVersion(capVer)
+}

cmd/k8s-operator/sts_test.go

@@ -61,10 +61,10 @@ func Test_applyProxyClassToStatefulSet(t *testing.T) {
 	proxyClassAllOpts := &tsapi.ProxyClass{
 		Spec: tsapi.ProxyClassSpec{
 			StatefulSet: &tsapi.StatefulSet{
-				Labels:      map[string]string{"foo": "bar"},
+				Labels:      tsapi.Labels{"foo": "bar"},
 				Annotations: map[string]string{"foo.io/bar": "foo"},
 				Pod: &tsapi.Pod{
-					Labels:      map[string]string{"bar": "foo"},
+					Labels:      tsapi.Labels{"bar": "foo"},
 					Annotations: map[string]string{"bar.io/foo": "foo"},
 					SecurityContext: &corev1.PodSecurityContext{
 						RunAsUser: ptr.To(int64(0)),
@@ -116,21 +116,36 @@ func Test_applyProxyClassToStatefulSet(t *testing.T) {
 	proxyClassJustLabels := &tsapi.ProxyClass{
 		Spec: tsapi.ProxyClassSpec{
 			StatefulSet: &tsapi.StatefulSet{
-				Labels:      map[string]string{"foo": "bar"},
+				Labels:      tsapi.Labels{"foo": "bar"},
 				Annotations: map[string]string{"foo.io/bar": "foo"},
 				Pod: &tsapi.Pod{
-					Labels:      map[string]string{"bar": "foo"},
+					Labels:      tsapi.Labels{"bar": "foo"},
 					Annotations: map[string]string{"bar.io/foo": "foo"},
 				},
 			},
 		},
 	}
-	proxyClassMetrics := &tsapi.ProxyClass{
-		Spec: tsapi.ProxyClassSpec{
-			Metrics: &tsapi.Metrics{Enable: true},
-		},
-	}
 
+	proxyClassWithMetricsDebug := func(metrics bool, debug *bool) *tsapi.ProxyClass {
+		return &tsapi.ProxyClass{
+			Spec: tsapi.ProxyClassSpec{
+				Metrics: &tsapi.Metrics{Enable: metrics},
+				StatefulSet: func() *tsapi.StatefulSet {
+					if debug == nil {
+						return nil
+					}
+
+					return &tsapi.StatefulSet{
+						Pod: &tsapi.Pod{
+							TailscaleContainer: &tsapi.Container{
+								Debug: &tsapi.Debug{Enable: *debug},
+							},
+						},
+					}
+				}(),
+			},
+		}
+	}
 	var userspaceProxySS, nonUserspaceProxySS appsv1.StatefulSet
 	if err := yaml.Unmarshal(userspaceProxyYaml, &userspaceProxySS); err != nil {
 		t.Fatalf("unmarshaling userspace proxy template: %v", err)
@@ -160,9 +175,9 @@ func Test_applyProxyClassToStatefulSet(t *testing.T) {
 	// 1. Test that a ProxyClass with all fields set gets correctly applied
 	// to a Statefulset built from non-userspace proxy template.
 	wantSS := nonUserspaceProxySS.DeepCopy()
-	wantSS.ObjectMeta.Labels = mergeMapKeys(wantSS.ObjectMeta.Labels, proxyClassAllOpts.Spec.StatefulSet.Labels)
-	wantSS.ObjectMeta.Annotations = mergeMapKeys(wantSS.ObjectMeta.Annotations, proxyClassAllOpts.Spec.StatefulSet.Annotations)
-	wantSS.Spec.Template.Labels = proxyClassAllOpts.Spec.StatefulSet.Pod.Labels
+	updateMap(wantSS.ObjectMeta.Labels, proxyClassAllOpts.Spec.StatefulSet.Labels.Parse())
+	updateMap(wantSS.ObjectMeta.Annotations, proxyClassAllOpts.Spec.StatefulSet.Annotations)
+	wantSS.Spec.Template.Labels = proxyClassAllOpts.Spec.StatefulSet.Pod.Labels.Parse()
 	wantSS.Spec.Template.Annotations = proxyClassAllOpts.Spec.StatefulSet.Pod.Annotations
 	wantSS.Spec.Template.Spec.SecurityContext = proxyClassAllOpts.Spec.StatefulSet.Pod.SecurityContext
 	wantSS.Spec.Template.Spec.ImagePullSecrets = proxyClassAllOpts.Spec.StatefulSet.Pod.ImagePullSecrets
@@ -184,28 +199,28 @@ func Test_applyProxyClassToStatefulSet(t *testing.T) {
 
 	gotSS := applyProxyClassToStatefulSet(proxyClassAllOpts, nonUserspaceProxySS.DeepCopy(), new(tailscaleSTSConfig), zl.Sugar())
 	if diff := cmp.Diff(gotSS, wantSS); diff != "" {
-		t.Fatalf("Unexpected result applying ProxyClass with all fields set to a StatefulSet for non-userspace proxy (-got +want):\n%s", diff)
+		t.Errorf("Unexpected result applying ProxyClass with all fields set to a StatefulSet for non-userspace proxy (-got +want):\n%s", diff)
 	}
 
 	// 2. Test that a ProxyClass with custom labels and annotations for
 	// StatefulSet and Pod set gets correctly applied to a Statefulset built
 	// from non-userspace proxy template.
 	wantSS = nonUserspaceProxySS.DeepCopy()
-	wantSS.ObjectMeta.Labels = mergeMapKeys(wantSS.ObjectMeta.Labels, proxyClassJustLabels.Spec.StatefulSet.Labels)
-	wantSS.ObjectMeta.Annotations = mergeMapKeys(wantSS.ObjectMeta.Annotations, proxyClassJustLabels.Spec.StatefulSet.Annotations)
-	wantSS.Spec.Template.Labels = proxyClassJustLabels.Spec.StatefulSet.Pod.Labels
+	updateMap(wantSS.ObjectMeta.Labels, proxyClassJustLabels.Spec.StatefulSet.Labels.Parse())
+	updateMap(wantSS.ObjectMeta.Annotations, proxyClassJustLabels.Spec.StatefulSet.Annotations)
+	wantSS.Spec.Template.Labels = proxyClassJustLabels.Spec.StatefulSet.Pod.Labels.Parse()
 	wantSS.Spec.Template.Annotations = proxyClassJustLabels.Spec.StatefulSet.Pod.Annotations
 	gotSS = applyProxyClassToStatefulSet(proxyClassJustLabels, nonUserspaceProxySS.DeepCopy(), new(tailscaleSTSConfig), zl.Sugar())
 	if diff := cmp.Diff(gotSS, wantSS); diff != "" {
-		t.Fatalf("Unexpected result applying ProxyClass with custom labels and annotations to a StatefulSet for non-userspace proxy (-got +want):\n%s", diff)
+		t.Errorf("Unexpected result applying ProxyClass with custom labels and annotations to a StatefulSet for non-userspace proxy (-got +want):\n%s", diff)
 	}
 
 	// 3. Test that a ProxyClass with all fields set gets correctly applied
 	// to a Statefulset built from a userspace proxy template.
 	wantSS = userspaceProxySS.DeepCopy()
-	wantSS.ObjectMeta.Labels = mergeMapKeys(wantSS.ObjectMeta.Labels, proxyClassAllOpts.Spec.StatefulSet.Labels)
-	wantSS.ObjectMeta.Annotations = mergeMapKeys(wantSS.ObjectMeta.Annotations, proxyClassAllOpts.Spec.StatefulSet.Annotations)
-	wantSS.Spec.Template.Labels = proxyClassAllOpts.Spec.StatefulSet.Pod.Labels
+	updateMap(wantSS.ObjectMeta.Labels, proxyClassAllOpts.Spec.StatefulSet.Labels.Parse())
+	updateMap(wantSS.ObjectMeta.Annotations, proxyClassAllOpts.Spec.StatefulSet.Annotations)
+	wantSS.Spec.Template.Labels = proxyClassAllOpts.Spec.StatefulSet.Pod.Labels.Parse()
 	wantSS.Spec.Template.Annotations = proxyClassAllOpts.Spec.StatefulSet.Pod.Annotations
 	wantSS.Spec.Template.Spec.SecurityContext = proxyClassAllOpts.Spec.StatefulSet.Pod.SecurityContext
 	wantSS.Spec.Template.Spec.ImagePullSecrets = proxyClassAllOpts.Spec.StatefulSet.Pod.ImagePullSecrets
@@ -221,36 +236,61 @@ func Test_applyProxyClassToStatefulSet(t *testing.T) {
 	wantSS.Spec.Template.Spec.Containers[0].Image = "ghcr.io/my-repo/tailscale:v0.01testsomething"
 	gotSS = applyProxyClassToStatefulSet(proxyClassAllOpts, userspaceProxySS.DeepCopy(), new(tailscaleSTSConfig), zl.Sugar())
 	if diff := cmp.Diff(gotSS, wantSS); diff != "" {
-		t.Fatalf("Unexpected result applying ProxyClass with all options to a StatefulSet for a userspace proxy (-got +want):\n%s", diff)
+		t.Errorf("Unexpected result applying ProxyClass with all options to a StatefulSet for a userspace proxy (-got +want):\n%s", diff)
 	}
 
 	// 4. Test that a ProxyClass with custom labels and annotations gets correctly applied
 	// to a Statefulset built from a userspace proxy template.
 	wantSS = userspaceProxySS.DeepCopy()
-	wantSS.ObjectMeta.Labels = mergeMapKeys(wantSS.ObjectMeta.Labels, proxyClassJustLabels.Spec.StatefulSet.Labels)
-	wantSS.ObjectMeta.Annotations = mergeMapKeys(wantSS.ObjectMeta.Annotations, proxyClassJustLabels.Spec.StatefulSet.Annotations)
-	wantSS.Spec.Template.Labels = proxyClassJustLabels.Spec.StatefulSet.Pod.Labels
+	updateMap(wantSS.ObjectMeta.Labels, proxyClassJustLabels.Spec.StatefulSet.Labels.Parse())
+	updateMap(wantSS.ObjectMeta.Annotations, proxyClassJustLabels.Spec.StatefulSet.Annotations)
+	wantSS.Spec.Template.Labels = proxyClassJustLabels.Spec.StatefulSet.Pod.Labels.Parse()
 	wantSS.Spec.Template.Annotations = proxyClassJustLabels.Spec.StatefulSet.Pod.Annotations
 	gotSS = applyProxyClassToStatefulSet(proxyClassJustLabels, userspaceProxySS.DeepCopy(), new(tailscaleSTSConfig), zl.Sugar())
 	if diff := cmp.Diff(gotSS, wantSS); diff != "" {
-		t.Fatalf("Unexpected result applying ProxyClass with custom labels and annotations to a StatefulSet for a userspace proxy (-got +want):\n%s", diff)
+		t.Errorf("Unexpected result applying ProxyClass with custom labels and annotations to a StatefulSet for a userspace proxy (-got +want):\n%s", diff)
 	}
 
-	// 5. Test that a ProxyClass with metrics enabled gets correctly applied to a StatefulSet.
+	// 5. Metrics enabled defaults to enabling both metrics and debug.
 	wantSS = nonUserspaceProxySS.DeepCopy()
-	wantSS.Spec.Template.Spec.Containers[0].Env = append(wantSS.Spec.Template.Spec.Containers[0].Env, corev1.EnvVar{Name: "TS_TAILSCALED_EXTRA_ARGS", Value: "--debug=$(POD_IP):9001"})
-	wantSS.Spec.Template.Spec.Containers[0].Ports = []corev1.ContainerPort{{Name: "metrics", Protocol: "TCP", ContainerPort: 9001, HostPort: 9001}}
-	gotSS = applyProxyClassToStatefulSet(proxyClassMetrics, nonUserspaceProxySS.DeepCopy(), new(tailscaleSTSConfig), zl.Sugar())
+	wantSS.Spec.Template.Spec.Containers[0].Env = append(wantSS.Spec.Template.Spec.Containers[0].Env,
+		corev1.EnvVar{Name: "TS_DEBUG_ADDR_PORT", Value: "$(POD_IP):9001"},
+		corev1.EnvVar{Name: "TS_TAILSCALED_EXTRA_ARGS", Value: "--debug=$(TS_DEBUG_ADDR_PORT)"},
+		corev1.EnvVar{Name: "TS_LOCAL_ADDR_PORT", Value: "$(POD_IP):9002"},
+		corev1.EnvVar{Name: "TS_ENABLE_METRICS", Value: "true"},
+	)
+	wantSS.Spec.Template.Spec.Containers[0].Ports = []corev1.ContainerPort{
+		{Name: "debug", Protocol: "TCP", ContainerPort: 9001},
+		{Name: "metrics", Protocol: "TCP", ContainerPort: 9002},
+	}
+	gotSS = applyProxyClassToStatefulSet(proxyClassWithMetricsDebug(true, nil), nonUserspaceProxySS.DeepCopy(), new(tailscaleSTSConfig), zl.Sugar())
 	if diff := cmp.Diff(gotSS, wantSS); diff != "" {
-		t.Fatalf("Unexpected result applying ProxyClass with metrics enabled to a StatefulSet (-got +want):\n%s", diff)
+		t.Errorf("Unexpected result applying ProxyClass with metrics enabled to a StatefulSet (-got +want):\n%s", diff)
 	}
-}
 
-func mergeMapKeys(a, b map[string]string) map[string]string {
-	for key, val := range b {
-		a[key] = val
+	// 6. Enable _just_ metrics by explicitly disabling debug.
+	wantSS = nonUserspaceProxySS.DeepCopy()
+	wantSS.Spec.Template.Spec.Containers[0].Env = append(wantSS.Spec.Template.Spec.Containers[0].Env,
+		corev1.EnvVar{Name: "TS_LOCAL_ADDR_PORT", Value: "$(POD_IP):9002"},
+		corev1.EnvVar{Name: "TS_ENABLE_METRICS", Value: "true"},
+	)
+	wantSS.Spec.Template.Spec.Containers[0].Ports = []corev1.ContainerPort{{Name: "metrics", Protocol: "TCP", ContainerPort: 9002}}
+	gotSS = applyProxyClassToStatefulSet(proxyClassWithMetricsDebug(true, ptr.To(false)), nonUserspaceProxySS.DeepCopy(), new(tailscaleSTSConfig), zl.Sugar())
+	if diff := cmp.Diff(gotSS, wantSS); diff != "" {
+		t.Errorf("Unexpected result applying ProxyClass with metrics enabled to a StatefulSet (-got +want):\n%s", diff)
+	}
+
+	// 7. Enable _just_ debug without metrics.
+	wantSS = nonUserspaceProxySS.DeepCopy()
+	wantSS.Spec.Template.Spec.Containers[0].Env = append(wantSS.Spec.Template.Spec.Containers[0].Env,
+		corev1.EnvVar{Name: "TS_DEBUG_ADDR_PORT", Value: "$(POD_IP):9001"},
+		corev1.EnvVar{Name: "TS_TAILSCALED_EXTRA_ARGS", Value: "--debug=$(TS_DEBUG_ADDR_PORT)"},
+	)
+	wantSS.Spec.Template.Spec.Containers[0].Ports = []corev1.ContainerPort{{Name: "debug", Protocol: "TCP", ContainerPort: 9001}}
+	gotSS = applyProxyClassToStatefulSet(proxyClassWithMetricsDebug(false, ptr.To(true)), nonUserspaceProxySS.DeepCopy(), new(tailscaleSTSConfig), zl.Sugar())
+	if diff := cmp.Diff(gotSS, wantSS); diff != "" {
+		t.Errorf("Unexpected result applying ProxyClass with metrics enabled to a StatefulSet (-got +want):\n%s", diff)
 	}
-	return a
 }
 
 func Test_mergeStatefulSetLabelsOrAnnots(t *testing.T) {
@@ -344,3 +384,10 @@ func Test_mergeStatefulSetLabelsOrAnnots(t *testing.T) {
 		})
 	}
 }
+
+// updateMap updates map a with the values from map b.
+func updateMap(a, b map[string]string) {
+	for key, val := range b {
+		a[key] = val
+	}
+}

cmd/k8s-operator/svc.go

@@ -121,7 +121,15 @@ func (a *ServiceReconciler) Reconcile(ctx context.Context, req reconcile.Request
 		return reconcile.Result{}, a.maybeCleanup(ctx, logger, svc)
 	}
 
-	return reconcile.Result{}, a.maybeProvision(ctx, logger, svc)
+	if err := a.maybeProvision(ctx, logger, svc); err != nil {
+		if strings.Contains(err.Error(), optimisticLockErrorMsg) {
+			logger.Infof("optimistic lock error, retrying: %s", err)
+		} else {
+			return reconcile.Result{}, err
+		}
+	}
+
+	return reconcile.Result{}, nil
 }
 
 // maybeCleanup removes any existing resources related to serving svc over tailscale.
@@ -131,7 +139,7 @@ func (a *ServiceReconciler) Reconcile(ctx context.Context, req reconcile.Request
 func (a *ServiceReconciler) maybeCleanup(ctx context.Context, logger *zap.SugaredLogger, svc *corev1.Service) (err error) {
 	oldSvcStatus := svc.Status.DeepCopy()
 	defer func() {
-		if !apiequality.Semantic.DeepEqual(oldSvcStatus, svc.Status) {
+		if !apiequality.Semantic.DeepEqual(oldSvcStatus, &svc.Status) {
 			// An error encountered here should get returned by the Reconcile function.
 			err = errors.Join(err, a.Client.Status().Update(ctx, svc))
 		}
@@ -152,7 +160,12 @@ func (a *ServiceReconciler) maybeCleanup(ctx context.Context, logger *zap.Sugare
 		return nil
 	}
 
-	if done, err := a.ssr.Cleanup(ctx, logger, childResourceLabels(svc.Name, svc.Namespace, "svc")); err != nil {
+	proxyTyp := proxyTypeEgress
+	if a.shouldExpose(svc) {
+		proxyTyp = proxyTypeIngressService
+	}
+
+	if done, err := a.ssr.Cleanup(ctx, logger, childResourceLabels(svc.Name, svc.Namespace, "svc"), proxyTyp); err != nil {
 		return fmt.Errorf("failed to cleanup: %w", err)
 	} else if !done {
 		logger.Debugf("cleanup not done yet, waiting for next reconcile")
@@ -191,7 +204,7 @@ func (a *ServiceReconciler) maybeCleanup(ctx context.Context, logger *zap.Sugare
 func (a *ServiceReconciler) maybeProvision(ctx context.Context, logger *zap.SugaredLogger, svc *corev1.Service) (err error) {
 	oldSvcStatus := svc.Status.DeepCopy()
 	defer func() {
-		if !apiequality.Semantic.DeepEqual(oldSvcStatus, svc.Status) {
+		if !apiequality.Semantic.DeepEqual(oldSvcStatus, &svc.Status) {
 			// An error encountered here should get returned by the Reconcile function.
 			err = errors.Join(err, a.Client.Status().Update(ctx, svc))
 		}
@@ -256,6 +269,10 @@ func (a *ServiceReconciler) maybeProvision(ctx context.Context, logger *zap.Suga
 		ChildResourceLabels: crl,
 		ProxyClassName:      proxyClass,
 	}
+	sts.proxyType = proxyTypeEgress
+	if a.shouldExpose(svc) {
+		sts.proxyType = proxyTypeIngressService
+	}
 
 	a.mu.Lock()
 	if a.shouldExposeClusterIP(svc) {
@@ -311,11 +328,11 @@ func (a *ServiceReconciler) maybeProvision(ctx context.Context, logger *zap.Suga
 		return nil
 	}
 
-	_, tsHost, tsIPs, err := a.ssr.DeviceInfo(ctx, crl)
+	dev, err := a.ssr.DeviceInfo(ctx, crl, logger)
 	if err != nil {
 		return fmt.Errorf("failed to get device ID: %w", err)
 	}
-	if tsHost == "" {
+	if dev == nil || dev.hostname == "" {
 		msg := "no Tailscale hostname known yet, waiting for proxy pod to finish auth"
 		logger.Debug(msg)
 		// No hostname yet. Wait for the proxy pod to auth.
@@ -324,9 +341,9 @@ func (a *ServiceReconciler) maybeProvision(ctx context.Context, logger *zap.Suga
 		return nil
 	}
 
-	logger.Debugf("setting Service LoadBalancer status to %q, %s", tsHost, strings.Join(tsIPs, ", "))
+	logger.Debugf("setting Service LoadBalancer status to %q, %s", dev.hostname, strings.Join(dev.ips, ", "))
 	ingress := []corev1.LoadBalancerIngress{
-		{Hostname: tsHost},
+		{Hostname: dev.hostname},
 	}
 	clusterIPAddr, err := netip.ParseAddr(svc.Spec.ClusterIP)
 	if err != nil {
@@ -334,7 +351,7 @@ func (a *ServiceReconciler) maybeProvision(ctx context.Context, logger *zap.Suga
 		tsoperator.SetServiceCondition(svc, tsapi.ProxyReady, metav1.ConditionFalse, reasonProxyFailed, msg, a.clock, logger)
 		return errors.New(msg)
 	}
-	for _, ip := range tsIPs {
+	for _, ip := range dev.ips {
 		addr, err := netip.ParseAddr(ip)
 		if err != nil {
 			continue

cmd/k8s-operator/testutils_test.go

@@ -8,6 +8,8 @@ package main
 import (
 	"context"
 	"encoding/json"
+	"fmt"
+	"net/http"
 	"net/netip"
 	"reflect"
 	"strings"
@@ -21,12 +23,14 @@ import (
 	corev1 "k8s.io/api/core/v1"
 	apierrors "k8s.io/apimachinery/pkg/api/errors"
 	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
+	"k8s.io/apimachinery/pkg/apis/meta/v1/unstructured"
 	"k8s.io/apimachinery/pkg/types"
 	"k8s.io/client-go/tools/record"
 	"sigs.k8s.io/controller-runtime/pkg/client"
 	"sigs.k8s.io/controller-runtime/pkg/reconcile"
 	"tailscale.com/client/tailscale"
 	"tailscale.com/ipn"
+	"tailscale.com/ipn/ipnstate"
 	tsapi "tailscale.com/k8s-operator/apis/v1alpha1"
 	"tailscale.com/types/ptr"
 	"tailscale.com/util/mak"
@@ -39,7 +43,10 @@ type configOpts struct {
 	secretName                                     string
 	hostname                                       string
 	namespace                                      string
+	tailscaleNamespace                             string
+	namespaced                                     bool
 	parentType                                     string
+	proxyType                                      string
 	priorityClassName                              string
 	firewallMode                                   string
 	tailnetTargetIP                                string
@@ -48,6 +55,7 @@ type configOpts struct {
 	clusterTargetDNS                               string
 	subnetRoutes                                   string
 	isExitNode                                     bool
+	isAppConnector                                 bool
 	confFileHash                                   string
 	serveConfig                                    *ipn.ServeConfig
 	shouldEnableForwardingClusterTrafficViaIngress bool
@@ -55,6 +63,10 @@ type configOpts struct {
 	app                                            string
 	shouldRemoveAuthKey                            bool
 	secretExtraData                                map[string][]byte
+	resourceVersion                                string
+
+	enableMetrics        bool
+	serviceMonitorLabels tsapi.Labels
 }
 
 func expectedSTS(t *testing.T, cl client.Client, opts configOpts) *appsv1.StatefulSet {
@@ -69,14 +81,13 @@ func expectedSTS(t *testing.T, cl client.Client, opts configOpts) *appsv1.Statef
 		Env: []corev1.EnvVar{
 			{Name: "TS_USERSPACE", Value: "false"},
 			{Name: "POD_IP", ValueFrom: &corev1.EnvVarSource{FieldRef: &corev1.ObjectFieldSelector{APIVersion: "", FieldPath: "status.podIP"}, ResourceFieldRef: nil, ConfigMapKeyRef: nil, SecretKeyRef: nil}},
+			{Name: "POD_NAME", ValueFrom: &corev1.EnvVarSource{FieldRef: &corev1.ObjectFieldSelector{APIVersion: "", FieldPath: "metadata.name"}, ResourceFieldRef: nil, ConfigMapKeyRef: nil, SecretKeyRef: nil}},
+			{Name: "POD_UID", ValueFrom: &corev1.EnvVarSource{FieldRef: &corev1.ObjectFieldSelector{APIVersion: "", FieldPath: "metadata.uid"}, ResourceFieldRef: nil, ConfigMapKeyRef: nil, SecretKeyRef: nil}},
 			{Name: "TS_KUBE_SECRET", Value: opts.secretName},
-			{Name: "EXPERIMENTAL_TS_CONFIGFILE_PATH", Value: "/etc/tsconfig/tailscaled"},
 			{Name: "TS_EXPERIMENTAL_VERSIONED_CONFIG_DIR", Value: "/etc/tsconfig"},
 		},
 		SecurityContext: &corev1.SecurityContext{
-			Capabilities: &corev1.Capabilities{
-				Add: []corev1.Capability{"NET_ADMIN"},
-			},
+			Privileged: ptr.To(true),
 		},
 		ImagePullPolicy: "Always",
 	}
@@ -86,7 +97,7 @@ func expectedSTS(t *testing.T, cl client.Client, opts configOpts) *appsv1.Statef
 			Value: "true",
 		})
 	}
-	annots := make(map[string]string)
+	var annots map[string]string
 	var volumes []corev1.Volume
 	volumes = []corev1.Volume{
 		{
@@ -104,7 +115,7 @@ func expectedSTS(t *testing.T, cl client.Client, opts configOpts) *appsv1.Statef
 		MountPath: "/etc/tsconfig",
 	}}
 	if opts.confFileHash != "" {
-		annots["tailscale.com/operator-last-set-config-file-hash"] = opts.confFileHash
+		mak.Set(&annots, "tailscale.com/operator-last-set-config-file-hash", opts.confFileHash)
 	}
 	if opts.firewallMode != "" {
 		tsContainer.Env = append(tsContainer.Env, corev1.EnvVar{
@@ -113,13 +124,13 @@ func expectedSTS(t *testing.T, cl client.Client, opts configOpts) *appsv1.Statef
 		})
 	}
 	if opts.tailnetTargetIP != "" {
-		annots["tailscale.com/operator-last-set-ts-tailnet-target-ip"] = opts.tailnetTargetIP
+		mak.Set(&annots, "tailscale.com/operator-last-set-ts-tailnet-target-ip", opts.tailnetTargetIP)
 		tsContainer.Env = append(tsContainer.Env, corev1.EnvVar{
 			Name:  "TS_TAILNET_TARGET_IP",
 			Value: opts.tailnetTargetIP,
 		})
 	} else if opts.tailnetTargetFQDN != "" {
-		annots["tailscale.com/operator-last-set-ts-tailnet-target-fqdn"] = opts.tailnetTargetFQDN
+		mak.Set(&annots, "tailscale.com/operator-last-set-ts-tailnet-target-fqdn", opts.tailnetTargetFQDN)
 		tsContainer.Env = append(tsContainer.Env, corev1.EnvVar{
 			Name:  "TS_TAILNET_TARGET_FQDN",
 			Value: opts.tailnetTargetFQDN,
@@ -130,13 +141,13 @@ func expectedSTS(t *testing.T, cl client.Client, opts configOpts) *appsv1.Statef
 			Name:  "TS_DEST_IP",
 			Value: opts.clusterTargetIP,
 		})
-		annots["tailscale.com/operator-last-set-cluster-ip"] = opts.clusterTargetIP
+		mak.Set(&annots, "tailscale.com/operator-last-set-cluster-ip", opts.clusterTargetIP)
 	} else if opts.clusterTargetDNS != "" {
 		tsContainer.Env = append(tsContainer.Env, corev1.EnvVar{
 			Name:  "TS_EXPERIMENTAL_DEST_DNS_NAME",
 			Value: opts.clusterTargetDNS,
 		})
-		annots["tailscale.com/operator-last-set-cluster-dns-name"] = opts.clusterTargetDNS
+		mak.Set(&annots, "tailscale.com/operator-last-set-cluster-dns-name", opts.clusterTargetDNS)
 	}
 	if opts.serveConfig != nil {
 		tsContainer.Env = append(tsContainer.Env, corev1.EnvVar{
@@ -150,6 +161,29 @@ func expectedSTS(t *testing.T, cl client.Client, opts configOpts) *appsv1.Statef
 		Name:  "TS_INTERNAL_APP",
 		Value: opts.app,
 	})
+	if opts.enableMetrics {
+		tsContainer.Env = append(tsContainer.Env,
+			corev1.EnvVar{
+				Name:  "TS_DEBUG_ADDR_PORT",
+				Value: "$(POD_IP):9001"},
+			corev1.EnvVar{
+				Name:  "TS_TAILSCALED_EXTRA_ARGS",
+				Value: "--debug=$(TS_DEBUG_ADDR_PORT)",
+			},
+			corev1.EnvVar{
+				Name:  "TS_LOCAL_ADDR_PORT",
+				Value: "$(POD_IP):9002",
+			},
+			corev1.EnvVar{
+				Name:  "TS_ENABLE_METRICS",
+				Value: "true",
+			},
+		)
+		tsContainer.Ports = append(tsContainer.Ports,
+			corev1.ContainerPort{Name: "debug", ContainerPort: 9001, Protocol: "TCP"},
+			corev1.ContainerPort{Name: "metrics", ContainerPort: 9002, Protocol: "TCP"},
+		)
+	}
 	ss := &appsv1.StatefulSet{
 		TypeMeta: metav1.TypeMeta{
 			Kind:       "StatefulSet",
@@ -228,8 +262,9 @@ func expectedSTSUserspace(t *testing.T, cl client.Client, opts configOpts) *apps
 		Env: []corev1.EnvVar{
 			{Name: "TS_USERSPACE", Value: "true"},
 			{Name: "POD_IP", ValueFrom: &corev1.EnvVarSource{FieldRef: &corev1.ObjectFieldSelector{APIVersion: "", FieldPath: "status.podIP"}, ResourceFieldRef: nil, ConfigMapKeyRef: nil, SecretKeyRef: nil}},
+			{Name: "POD_NAME", ValueFrom: &corev1.EnvVarSource{FieldRef: &corev1.ObjectFieldSelector{APIVersion: "", FieldPath: "metadata.name"}, ResourceFieldRef: nil, ConfigMapKeyRef: nil, SecretKeyRef: nil}},
+			{Name: "POD_UID", ValueFrom: &corev1.EnvVarSource{FieldRef: &corev1.ObjectFieldSelector{APIVersion: "", FieldPath: "metadata.uid"}, ResourceFieldRef: nil, ConfigMapKeyRef: nil, SecretKeyRef: nil}},
 			{Name: "TS_KUBE_SECRET", Value: opts.secretName},
-			{Name: "EXPERIMENTAL_TS_CONFIGFILE_PATH", Value: "/etc/tsconfig/tailscaled"},
 			{Name: "TS_EXPERIMENTAL_VERSIONED_CONFIG_DIR", Value: "/etc/tsconfig"},
 			{Name: "TS_SERVE_CONFIG", Value: "/etc/tailscaled/serve-config"},
 			{Name: "TS_INTERNAL_APP", Value: opts.app},
@@ -240,6 +275,29 @@ func expectedSTSUserspace(t *testing.T, cl client.Client, opts configOpts) *apps
 			{Name: "serve-config", ReadOnly: true, MountPath: "/etc/tailscaled"},
 		},
 	}
+	if opts.enableMetrics {
+		tsContainer.Env = append(tsContainer.Env,
+			corev1.EnvVar{
+				Name:  "TS_DEBUG_ADDR_PORT",
+				Value: "$(POD_IP):9001"},
+			corev1.EnvVar{
+				Name:  "TS_TAILSCALED_EXTRA_ARGS",
+				Value: "--debug=$(TS_DEBUG_ADDR_PORT)",
+			},
+			corev1.EnvVar{
+				Name:  "TS_LOCAL_ADDR_PORT",
+				Value: "$(POD_IP):9002",
+			},
+			corev1.EnvVar{
+				Name:  "TS_ENABLE_METRICS",
+				Value: "true",
+			},
+		)
+		tsContainer.Ports = append(tsContainer.Ports, corev1.ContainerPort{
+			Name: "debug", ContainerPort: 9001, Protocol: "TCP"},
+			corev1.ContainerPort{Name: "metrics", ContainerPort: 9002, Protocol: "TCP"},
+		)
+	}
 	volumes := []corev1.Volume{
 		{
 			Name: "tailscaledconfig",
@@ -334,6 +392,90 @@ func expectedHeadlessService(name string, parentType string) *corev1.Service {
 	}
 }
 
+func expectedMetricsService(opts configOpts) *corev1.Service {
+	labels := metricsLabels(opts)
+	selector := map[string]string{
+		"tailscale.com/managed":              "true",
+		"tailscale.com/parent-resource":      "test",
+		"tailscale.com/parent-resource-type": opts.parentType,
+	}
+	if opts.namespaced {
+		selector["tailscale.com/parent-resource-ns"] = opts.namespace
+	}
+	return &corev1.Service{
+		ObjectMeta: metav1.ObjectMeta{
+			Name:      metricsResourceName(opts.stsName),
+			Namespace: opts.tailscaleNamespace,
+			Labels:    labels,
+		},
+		Spec: corev1.ServiceSpec{
+			Selector: selector,
+			Type:     corev1.ServiceTypeClusterIP,
+			Ports:    []corev1.ServicePort{{Protocol: "TCP", Port: 9002, Name: "metrics"}},
+		},
+	}
+}
+
+func metricsLabels(opts configOpts) map[string]string {
+	promJob := fmt.Sprintf("ts_%s_default_test", opts.proxyType)
+	if !opts.namespaced {
+		promJob = fmt.Sprintf("ts_%s_test", opts.proxyType)
+	}
+	labels := map[string]string{
+		"tailscale.com/managed":        "true",
+		"tailscale.com/metrics-target": opts.stsName,
+		"ts_prom_job":                  promJob,
+		"ts_proxy_type":                opts.proxyType,
+		"ts_proxy_parent_name":         "test",
+	}
+	if opts.namespaced {
+		labels["ts_proxy_parent_namespace"] = "default"
+	}
+	return labels
+}
+
+func expectedServiceMonitor(t *testing.T, opts configOpts) *unstructured.Unstructured {
+	t.Helper()
+	smLabels := metricsLabels(opts)
+	if len(opts.serviceMonitorLabels) != 0 {
+		smLabels = mergeMapKeys(smLabels, opts.serviceMonitorLabels.Parse())
+	}
+	name := metricsResourceName(opts.stsName)
+	sm := &ServiceMonitor{
+		ObjectMeta: metav1.ObjectMeta{
+			Name:            name,
+			Namespace:       opts.tailscaleNamespace,
+			Labels:          smLabels,
+			ResourceVersion: opts.resourceVersion,
+			OwnerReferences: []metav1.OwnerReference{{APIVersion: "v1", Kind: "Service", Name: name, BlockOwnerDeletion: ptr.To(true), Controller: ptr.To(true)}},
+		},
+		TypeMeta: metav1.TypeMeta{
+			Kind:       "ServiceMonitor",
+			APIVersion: "monitoring.coreos.com/v1",
+		},
+		Spec: ServiceMonitorSpec{
+			Selector: metav1.LabelSelector{MatchLabels: metricsLabels(opts)},
+			Endpoints: []ServiceMonitorEndpoint{{
+				Port: "metrics",
+			}},
+			NamespaceSelector: ServiceMonitorNamespaceSelector{
+				MatchNames: []string{opts.tailscaleNamespace},
+			},
+			JobLabel: "ts_prom_job",
+			TargetLabels: []string{
+				"ts_proxy_parent_name",
+				"ts_proxy_parent_namespace",
+				"ts_proxy_type",
+			},
+		},
+	}
+	u, err := serviceMonitorToUnstructured(sm)
+	if err != nil {
+		t.Fatalf("error converting ServiceMonitor to unstructured: %v", err)
+	}
+	return u
+}
+
 func expectedSecret(t *testing.T, cl client.Client, opts configOpts) *corev1.Secret {
 	t.Helper()
 	s := &corev1.Secret{
@@ -350,12 +492,14 @@ func expectedSecret(t *testing.T, cl client.Client, opts configOpts) *corev1.Sec
 		mak.Set(&s.StringData, "serve-config", string(serveConfigBs))
 	}
 	conf := &ipn.ConfigVAlpha{
-		Version:      "alpha0",
-		AcceptDNS:    "false",
-		Hostname:     &opts.hostname,
-		Locked:       "false",
-		AuthKey:      ptr.To("secret-authkey"),
-		AcceptRoutes: "false",
+		Version:             "alpha0",
+		AcceptDNS:           "false",
+		Hostname:            &opts.hostname,
+		Locked:              "false",
+		AuthKey:             ptr.To("secret-authkey"),
+		AcceptRoutes:        "false",
+		AppConnector:        &ipn.AppConnectorPrefs{Advertise: false},
+		NoStatefulFiltering: "true",
 	}
 	if opts.proxyClass != "" {
 		t.Logf("applying configuration from ProxyClass %s", opts.proxyClass)
@@ -370,6 +514,9 @@ func expectedSecret(t *testing.T, cl client.Client, opts configOpts) *corev1.Sec
 	if opts.shouldRemoveAuthKey {
 		conf.AuthKey = nil
 	}
+	if opts.isAppConnector {
+		conf.AppConnector = &ipn.AppConnectorPrefs{Advertise: true}
+	}
 	var routes []netip.Prefix
 	if opts.subnetRoutes != "" || opts.isExitNode {
 		r := opts.subnetRoutes
@@ -385,21 +532,17 @@ func expectedSecret(t *testing.T, cl client.Client, opts configOpts) *corev1.Sec
 		}
 	}
 	conf.AdvertiseRoutes = routes
-	b, err := json.Marshal(conf)
+	bnn, err := json.Marshal(conf)
 	if err != nil {
 		t.Fatalf("error marshalling tailscaled config")
 	}
-	if opts.tailnetTargetFQDN != "" || opts.tailnetTargetIP != "" {
-		conf.NoStatefulFiltering = "true"
-	} else {
-		conf.NoStatefulFiltering = "false"
-	}
+	conf.AppConnector = nil
 	bn, err := json.Marshal(conf)
 	if err != nil {
 		t.Fatalf("error marshalling tailscaled config")
 	}
-	mak.Set(&s.StringData, "tailscaled", string(b))
 	mak.Set(&s.StringData, "cap-95.hujson", string(bn))
+	mak.Set(&s.StringData, "cap-107.hujson", string(bnn))
 	labels := map[string]string{
 		"tailscale.com/managed":              "true",
 		"tailscale.com/parent-resource":      "test",
@@ -477,7 +620,7 @@ func mustUpdateStatus[T any, O ptrObject[T]](t *testing.T, client client.Client,
 // modify func to ensure that they are removed from the cluster object and the
 // object passed as 'want'. If no such modifications are needed, you can pass
 // nil in place of the modify function.
-func expectEqual[T any, O ptrObject[T]](t *testing.T, client client.Client, want O, modifier func(O)) {
+func expectEqual[T any, O ptrObject[T]](t *testing.T, client client.Client, want O, modifiers ...func(O)) {
 	t.Helper()
 	got := O(new(T))
 	if err := client.Get(context.Background(), types.NamespacedName{
@@ -491,7 +634,7 @@ func expectEqual[T any, O ptrObject[T]](t *testing.T, client client.Client, want
 	// so just remove it from both got and want.
 	got.SetResourceVersion("")
 	want.SetResourceVersion("")
-	if modifier != nil {
+	for _, modifier := range modifiers {
 		modifier(want)
 		modifier(got)
 	}
@@ -500,13 +643,29 @@ func expectEqual[T any, O ptrObject[T]](t *testing.T, client client.Client, want
 	}
 }
 
+func expectEqualUnstructured(t *testing.T, client client.Client, want *unstructured.Unstructured) {
+	t.Helper()
+	got := &unstructured.Unstructured{}
+	got.SetGroupVersionKind(want.GroupVersionKind())
+	if err := client.Get(context.Background(), types.NamespacedName{
+		Name:      want.GetName(),
+		Namespace: want.GetNamespace(),
+	}, got); err != nil {
+		t.Fatalf("getting %q: %v", want.GetName(), err)
+	}
+	if diff := cmp.Diff(got, want); diff != "" {
+		t.Fatalf("unexpected contents of Unstructured (-got +want):\n%s", diff)
+	}
+}
+
 func expectMissing[T any, O ptrObject[T]](t *testing.T, client client.Client, ns, name string) {
 	t.Helper()
 	obj := O(new(T))
-	if err := client.Get(context.Background(), types.NamespacedName{
+	err := client.Get(context.Background(), types.NamespacedName{
 		Name:      name,
 		Namespace: ns,
-	}, obj); !apierrors.IsNotFound(err) {
+	}, obj)
+	if !apierrors.IsNotFound(err) {
 		t.Fatalf("%s %s/%s unexpectedly present, wanted missing", reflect.TypeOf(obj).Elem().Name(), ns, name)
 	}
 }
@@ -580,6 +739,7 @@ type fakeTSClient struct {
 	sync.Mutex
 	keyRequests []tailscale.KeyCapabilities
 	deleted     []string
+	vipServices map[string]*VIPService
 }
 type fakeTSNetServer struct {
 	certDomains []string
@@ -637,12 +797,21 @@ func (c *fakeTSClient) Deleted() []string {
 // change to the configfile contents).
 func removeHashAnnotation(sts *appsv1.StatefulSet) {
 	delete(sts.Spec.Template.Annotations, podAnnotationLastSetConfigFileHash)
+	if len(sts.Spec.Template.Annotations) == 0 {
+		sts.Spec.Template.Annotations = nil
+	}
+}
+
+func removeResourceReqs(sts *appsv1.StatefulSet) {
+	if sts != nil {
+		sts.Spec.Template.Spec.Resources = nil
+	}
 }
 
 func removeTargetPortsFromSvc(svc *corev1.Service) {
 	newPorts := make([]corev1.ServicePort, 0)
 	for _, p := range svc.Spec.Ports {
-		newPorts = append(newPorts, corev1.ServicePort{Protocol: p.Protocol, Port: p.Port})
+		newPorts = append(newPorts, corev1.ServicePort{Protocol: p.Protocol, Port: p.Port, Name: p.Name})
 	}
 	svc.Spec.Ports = newPorts
 }
@@ -650,18 +819,6 @@ func removeTargetPortsFromSvc(svc *corev1.Service) {
 func removeAuthKeyIfExistsModifier(t *testing.T) func(s *corev1.Secret) {
 	return func(secret *corev1.Secret) {
 		t.Helper()
-		if len(secret.StringData["tailscaled"]) != 0 {
-			conf := &ipn.ConfigVAlpha{}
-			if err := json.Unmarshal([]byte(secret.StringData["tailscaled"]), conf); err != nil {
-				t.Fatalf("error unmarshalling 'tailscaled' contents: %v", err)
-			}
-			conf.AuthKey = nil
-			b, err := json.Marshal(conf)
-			if err != nil {
-				t.Fatalf("error marshalling updated 'tailscaled' config: %v", err)
-			}
-			mak.Set(&secret.StringData, "tailscaled", string(b))
-		}
 		if len(secret.StringData["cap-95.hujson"]) != 0 {
 			conf := &ipn.ConfigVAlpha{}
 			if err := json.Unmarshal([]byte(secret.StringData["cap-95.hujson"]), conf); err != nil {
@@ -674,5 +831,64 @@ func removeAuthKeyIfExistsModifier(t *testing.T) func(s *corev1.Secret) {
 			}
 			mak.Set(&secret.StringData, "cap-95.hujson", string(b))
 		}
+		if len(secret.StringData["cap-107.hujson"]) != 0 {
+			conf := &ipn.ConfigVAlpha{}
+			if err := json.Unmarshal([]byte(secret.StringData["cap-107.hujson"]), conf); err != nil {
+				t.Fatalf("error umarshalling 'cap-107.hujson' contents: %v", err)
+			}
+			conf.AuthKey = nil
+			b, err := json.Marshal(conf)
+			if err != nil {
+				t.Fatalf("error marshalling 'cap-107.huson' contents: %v", err)
+			}
+			mak.Set(&secret.StringData, "cap-107.hujson", string(b))
+		}
 	}
 }
+
+func (c *fakeTSClient) getVIPServiceByName(ctx context.Context, name string) (*VIPService, error) {
+	c.Lock()
+	defer c.Unlock()
+	if c.vipServices == nil {
+		return nil, &tailscale.ErrResponse{Status: http.StatusNotFound}
+	}
+	svc, ok := c.vipServices[name]
+	if !ok {
+		return nil, &tailscale.ErrResponse{Status: http.StatusNotFound}
+	}
+	return svc, nil
+}
+
+func (c *fakeTSClient) createOrUpdateVIPServiceByName(ctx context.Context, svc *VIPService) error {
+	c.Lock()
+	defer c.Unlock()
+	if c.vipServices == nil {
+		c.vipServices = make(map[string]*VIPService)
+	}
+	c.vipServices[svc.Name] = svc
+	return nil
+}
+
+func (c *fakeTSClient) deleteVIPServiceByName(ctx context.Context, name string) error {
+	c.Lock()
+	defer c.Unlock()
+	if c.vipServices != nil {
+		delete(c.vipServices, name)
+	}
+	return nil
+}
+
+type fakeLocalClient struct {
+	status *ipnstate.Status
+}
+
+func (f *fakeLocalClient) StatusWithoutPeers(ctx context.Context) (*ipnstate.Status, error) {
+	if f.status == nil {
+		return &ipnstate.Status{
+			Self: &ipnstate.PeerStatus{
+				DNSName: "test-node.test.ts.net.",
+			},
+		}, nil
+	}
+	return f.status, nil
+}

cmd/k8s-operator/tsclient.go

@@ -0,0 +1,185 @@
+// Copyright (c) Tailscale Inc & AUTHORS
+// SPDX-License-Identifier: BSD-3-Clause
+
+//go:build !plan9
+
+package main
+
+import (
+	"bytes"
+	"context"
+	"encoding/json"
+	"fmt"
+	"io"
+	"net/http"
+	"net/url"
+	"os"
+
+	"golang.org/x/oauth2/clientcredentials"
+	"tailscale.com/client/tailscale"
+	"tailscale.com/util/httpm"
+)
+
+// defaultTailnet is a value that can be used in Tailscale API calls instead of tailnet name to indicate that the API
+// call should be performed on the default tailnet for the provided credentials.
+const (
+	defaultTailnet = "-"
+	defaultBaseURL = "https://api.tailscale.com"
+)
+
+func newTSClient(ctx context.Context, clientIDPath, clientSecretPath string) (tsClient, error) {
+	clientID, err := os.ReadFile(clientIDPath)
+	if err != nil {
+		return nil, fmt.Errorf("error reading client ID %q: %w", clientIDPath, err)
+	}
+	clientSecret, err := os.ReadFile(clientSecretPath)
+	if err != nil {
+		return nil, fmt.Errorf("reading client secret %q: %w", clientSecretPath, err)
+	}
+	credentials := clientcredentials.Config{
+		ClientID:     string(clientID),
+		ClientSecret: string(clientSecret),
+		TokenURL:     "https://login.tailscale.com/api/v2/oauth/token",
+	}
+	c := tailscale.NewClient(defaultTailnet, nil)
+	c.UserAgent = "tailscale-k8s-operator"
+	c.HTTPClient = credentials.Client(ctx)
+	tsc := &tsClientImpl{
+		Client:  c,
+		baseURL: defaultBaseURL,
+		tailnet: defaultTailnet,
+	}
+	return tsc, nil
+}
+
+type tsClient interface {
+	CreateKey(ctx context.Context, caps tailscale.KeyCapabilities) (string, *tailscale.Key, error)
+	Device(ctx context.Context, deviceID string, fields *tailscale.DeviceFieldsOpts) (*tailscale.Device, error)
+	DeleteDevice(ctx context.Context, nodeStableID string) error
+	getVIPServiceByName(ctx context.Context, name string) (*VIPService, error)
+	createOrUpdateVIPServiceByName(ctx context.Context, svc *VIPService) error
+	deleteVIPServiceByName(ctx context.Context, name string) error
+}
+
+type tsClientImpl struct {
+	*tailscale.Client
+	baseURL string
+	tailnet string
+}
+
+// VIPService is a Tailscale VIPService with Tailscale API JSON representation.
+type VIPService struct {
+	// Name is the leftmost label of the DNS name of the VIP service.
+	// Name is required.
+	Name string `json:"name,omitempty"`
+	// Addrs are the IP addresses of the VIP Service. There are two addresses:
+	// the first is IPv4 and the second is IPv6.
+	// When creating a new VIP Service, the IP addresses are optional: if no
+	// addresses are specified then they will be selected. If an IPv4 address is
+	// specified at index 0, then that address will attempt to be used. An IPv6
+	// address can not be specified upon creation.
+	Addrs []string `json:"addrs,omitempty"`
+	// Comment is an optional text string for display in the admin panel.
+	Comment string `json:"comment,omitempty"`
+	// Ports are the ports of a VIPService that will be configured via Tailscale serve config.
+	// If set, any node wishing to advertise this VIPService must have this port configured via Tailscale serve.
+	Ports []string `json:"ports,omitempty"`
+	// Tags are optional ACL tags that will be applied to the VIPService.
+	Tags []string `json:"tags,omitempty"`
+}
+
+// GetVIPServiceByName retrieves a VIPService by its name. It returns 404 if the VIPService is not found.
+func (c *tsClientImpl) getVIPServiceByName(ctx context.Context, name string) (*VIPService, error) {
+	path := fmt.Sprintf("%s/api/v2/tailnet/%s/vip-services/by-name/%s", c.baseURL, c.tailnet, url.PathEscape(name))
+	req, err := http.NewRequestWithContext(ctx, httpm.GET, path, nil)
+	if err != nil {
+		return nil, fmt.Errorf("error creating new HTTP request: %w", err)
+	}
+	b, resp, err := c.sendRequest(req)
+	if err != nil {
+		return nil, fmt.Errorf("error making Tailsale API request: %w", err)
+	}
+	// If status code was not successful, return the error.
+	// TODO: Change the check for the StatusCode to include other 2XX success codes.
+	if resp.StatusCode != http.StatusOK {
+		return nil, handleErrorResponse(b, resp)
+	}
+	svc := &VIPService{}
+	if err := json.Unmarshal(b, svc); err != nil {
+		return nil, err
+	}
+	return svc, nil
+}
+
+// CreateOrUpdateVIPServiceByName creates or updates a VIPService by its name. Caller must ensure that, if the
+// VIPService already exists, the VIPService is fetched first to ensure that any auto-allocated IP addresses are not
+// lost during the update. If the VIPService was created without any IP addresses explicitly set (so that they were
+// auto-allocated by Tailscale) any subsequent request to this function that does not set any IP addresses will error.
+func (c *tsClientImpl) createOrUpdateVIPServiceByName(ctx context.Context, svc *VIPService) error {
+	data, err := json.Marshal(svc)
+	if err != nil {
+		return err
+	}
+	path := fmt.Sprintf("%s/api/v2/tailnet/%s/vip-services/by-name/%s", c.baseURL, c.tailnet, url.PathEscape(svc.Name))
+	req, err := http.NewRequestWithContext(ctx, httpm.PUT, path, bytes.NewBuffer(data))
+	if err != nil {
+		return fmt.Errorf("error creating new HTTP request: %w", err)
+	}
+	b, resp, err := c.sendRequest(req)
+	if err != nil {
+		return fmt.Errorf("error making Tailscale API request: %w", err)
+	}
+	// If status code was not successful, return the error.
+	// TODO: Change the check for the StatusCode to include other 2XX success codes.
+	if resp.StatusCode != http.StatusOK {
+		return handleErrorResponse(b, resp)
+	}
+	return nil
+}
+
+// DeleteVIPServiceByName deletes a VIPService by its name. It returns an error if the VIPService
+// does not exist or if the deletion fails.
+func (c *tsClientImpl) deleteVIPServiceByName(ctx context.Context, name string) error {
+	path := fmt.Sprintf("%s/api/v2/tailnet/%s/vip-services/by-name/%s", c.baseURL, c.tailnet, url.PathEscape(name))
+	req, err := http.NewRequestWithContext(ctx, httpm.DELETE, path, nil)
+	if err != nil {
+		return fmt.Errorf("error creating new HTTP request: %w", err)
+	}
+	b, resp, err := c.sendRequest(req)
+	if err != nil {
+		return fmt.Errorf("error making Tailscale API request: %w", err)
+	}
+	// If status code was not successful, return the error.
+	if resp.StatusCode != http.StatusOK {
+		return handleErrorResponse(b, resp)
+	}
+	return nil
+}
+
+// sendRequest add the authentication key to the request and sends it. It
+// receives the response and reads up to 10MB of it.
+func (c *tsClientImpl) sendRequest(req *http.Request) ([]byte, *http.Response, error) {
+	resp, err := c.Do(req)
+	if err != nil {
+		return nil, resp, fmt.Errorf("error actually doing request: %w", err)
+	}
+	defer resp.Body.Close()
+
+	// Read response
+	b, err := io.ReadAll(resp.Body)
+	if err != nil {
+		err = fmt.Errorf("error reading response body: %v", err)
+	}
+	return b, resp, err
+}
+
+// handleErrorResponse decodes the error message from the server and returns
+// an ErrResponse from it.
+func handleErrorResponse(b []byte, resp *http.Response) error {
+	var errResp tailscale.ErrResponse
+	if err := json.Unmarshal(b, &errResp); err != nil {
+		return err
+	}
+	errResp.Status = resp.StatusCode
+	return errResp
+}

cmd/k8s-operator/tsrecorder.go

@@ -11,6 +11,7 @@ import (
 	"fmt"
 	"net/http"
 	"slices"
+	"strings"
 	"sync"
 
 	"github.com/pkg/errors"
@@ -38,6 +39,7 @@ import (
 
 const (
 	reasonRecorderCreationFailed = "RecorderCreationFailed"
+	reasonRecorderCreating       = "RecorderCreating"
 	reasonRecorderCreated        = "RecorderCreated"
 	reasonRecorderInvalid        = "RecorderInvalid"
 
@@ -102,7 +104,7 @@ func (r *RecorderReconciler) Reconcile(ctx context.Context, req reconcile.Reques
 	oldTSRStatus := tsr.Status.DeepCopy()
 	setStatusReady := func(tsr *tsapi.Recorder, status metav1.ConditionStatus, reason, message string) (reconcile.Result, error) {
 		tsoperator.SetRecorderCondition(tsr, tsapi.RecorderReady, status, reason, message, tsr.Generation, r.clock, logger)
-		if !apiequality.Semantic.DeepEqual(oldTSRStatus, tsr.Status) {
+		if !apiequality.Semantic.DeepEqual(oldTSRStatus, &tsr.Status) {
 			// An error encountered here should get returned by the Reconcile function.
 			if updateErr := r.Client.Status().Update(ctx, tsr); updateErr != nil {
 				err = errors.Wrap(err, updateErr.Error())
@@ -119,23 +121,28 @@ func (r *RecorderReconciler) Reconcile(ctx context.Context, req reconcile.Reques
 		logger.Infof("ensuring Recorder is set up")
 		tsr.Finalizers = append(tsr.Finalizers, FinalizerName)
 		if err := r.Update(ctx, tsr); err != nil {
-			logger.Errorf("error adding finalizer: %w", err)
 			return setStatusReady(tsr, metav1.ConditionFalse, reasonRecorderCreationFailed, reasonRecorderCreationFailed)
 		}
 	}
 
 	if err := r.validate(tsr); err != nil {
-		logger.Errorf("error validating Recorder spec: %w", err)
 		message := fmt.Sprintf("Recorder is invalid: %s", err)
 		r.recorder.Eventf(tsr, corev1.EventTypeWarning, reasonRecorderInvalid, message)
 		return setStatusReady(tsr, metav1.ConditionFalse, reasonRecorderInvalid, message)
 	}
 
 	if err = r.maybeProvision(ctx, tsr); err != nil {
-		logger.Errorf("error creating Recorder resources: %w", err)
+		reason := reasonRecorderCreationFailed
 		message := fmt.Sprintf("failed creating Recorder: %s", err)
-		r.recorder.Eventf(tsr, corev1.EventTypeWarning, reasonRecorderCreationFailed, message)
-		return setStatusReady(tsr, metav1.ConditionFalse, reasonRecorderCreationFailed, message)
+		if strings.Contains(err.Error(), optimisticLockErrorMsg) {
+			reason = reasonRecorderCreating
+			message = fmt.Sprintf("optimistic lock error, retrying: %s", err)
+			err = nil
+			logger.Info(message)
+		} else {
+			r.recorder.Eventf(tsr, corev1.EventTypeWarning, reasonRecorderCreationFailed, message)
+		}
+		return setStatusReady(tsr, metav1.ConditionFalse, reason, message)
 	}
 
 	logger.Info("Recorder resources synced")

cmd/k8s-operator/tsrecorder_specs.go

@@ -130,6 +130,15 @@ func tsrRole(tsr *tsapi.Recorder, namespace string) *rbacv1.Role {
 					fmt.Sprintf("%s-0", tsr.Name), // Contains the node state.
 				},
 			},
+			{
+				APIGroups: []string{""},
+				Resources: []string{"events"},
+				Verbs: []string{
+					"get",
+					"create",
+					"patch",
+				},
+			},
 		},
 	}
 }
@@ -203,6 +212,14 @@ func env(tsr *tsapi.Recorder) []corev1.EnvVar {
 				},
 			},
 		},
+		{
+			Name: "POD_UID",
+			ValueFrom: &corev1.EnvVarSource{
+				FieldRef: &corev1.ObjectFieldSelector{
+					FieldPath: "metadata.uid",
+				},
+			},
+		},
 		{
 			Name:  "TS_STATE",
 			Value: "kube:$(POD_NAME)",

cmd/k8s-operator/tsrecorder_test.go

@@ -57,7 +57,7 @@ func TestRecorder(t *testing.T) {
 
 		msg := "Recorder is invalid: must either enable UI or use S3 storage to ensure recordings are accessible"
 		tsoperator.SetRecorderCondition(tsr, tsapi.RecorderReady, metav1.ConditionFalse, reasonRecorderInvalid, msg, 0, cl, zl.Sugar())
-		expectEqual(t, fc, tsr, nil)
+		expectEqual(t, fc, tsr)
 		if expected := 0; reconciler.recorders.Len() != expected {
 			t.Fatalf("expected %d recorders, got %d", expected, reconciler.recorders.Len())
 		}
@@ -76,7 +76,7 @@ func TestRecorder(t *testing.T) {
 		expectReconciled(t, reconciler, "", tsr.Name)
 
 		tsoperator.SetRecorderCondition(tsr, tsapi.RecorderReady, metav1.ConditionTrue, reasonRecorderCreated, reasonRecorderCreated, 0, cl, zl.Sugar())
-		expectEqual(t, fc, tsr, nil)
+		expectEqual(t, fc, tsr)
 		if expected := 1; reconciler.recorders.Len() != expected {
 			t.Fatalf("expected %d recorders, got %d", expected, reconciler.recorders.Len())
 		}
@@ -112,7 +112,7 @@ func TestRecorder(t *testing.T) {
 				URL:        "https://test-0.example.ts.net",
 			},
 		}
-		expectEqual(t, fc, tsr, nil)
+		expectEqual(t, fc, tsr)
 	})
 
 	t.Run("delete the Recorder and observe cleanup", func(t *testing.T) {
@@ -145,12 +145,12 @@ func expectRecorderResources(t *testing.T, fc client.WithWatch, tsr *tsapi.Recor
 	statefulSet := tsrStatefulSet(tsr, tsNamespace)
 
 	if shouldExist {
-		expectEqual(t, fc, auth, nil)
-		expectEqual(t, fc, state, nil)
-		expectEqual(t, fc, role, nil)
-		expectEqual(t, fc, roleBinding, nil)
-		expectEqual(t, fc, serviceAccount, nil)
-		expectEqual(t, fc, statefulSet, nil)
+		expectEqual(t, fc, auth)
+		expectEqual(t, fc, state)
+		expectEqual(t, fc, role)
+		expectEqual(t, fc, roleBinding)
+		expectEqual(t, fc, serviceAccount)
+		expectEqual(t, fc, statefulSet, removeResourceReqs)
 	} else {
 		expectMissing[corev1.Secret](t, fc, auth.Namespace, auth.Name)
 		expectMissing[corev1.Secret](t, fc, state.Namespace, state.Name)

cmd/lopower/README.md

@@ -1,39 +0,0 @@
-# Tailscale LOPOWER
-
-"Little Opinionated Proxy Over Wireguard-encrypted Routes"
-
-**STATUS**: in-development alpha (as of 2024-11-03)
- 
-## Background
-
-Some small devices such as ESP32 microcontrollers [support WireGuard](https://github.com/ciniml/WireGuard-ESP32-Arduino) but are too small to run Tailscale.
-
-Tailscale LOPOWER is a proxy that you run nearby that bridges a low-power WireGuard-speaking device on one side to Tailscale on the other side. That way network traffic from the low-powered device never hits the network unencrypted but is still able to communicate to/from other Tailscale devices on your Tailnet.
-
-## Diagram
-
-<img src="./lopower.svg">
-
-## Features
-
-* Runs separate Wireguard server with separate keys (unknown to the Tailscale control plane) that proxy on to Tailscale
-* Outputs WireGuard-standard configuration to enrolls devices, including in QR code form.
-* embeds `tsnet`, with an identity on which the device(s) behind the proxy appear on your Tailnet
-* optional IPv4 support. IPv6 is always enabled, as it never conflicts with anything. But IPv4 (or CGNAT) might already be in use on your client's network.
-* includes a DNS server (at `fd7a:115c:a1e0:9909::1` by default and optionally also at `10.90.0.1`) to serve both MagicDNS names as well as forwarding non-Tailscale DNS names onwards
-    * if IPv4 is disabled, MagicDNS `A` records are filtered out, and only `AAAA` records are served.
-
-## Limitations
-
-* this runs in userspace using gVisor's netstack. That means it's portable (and doesn't require kernel/system configuration), but that does mean it doesn't operate at a packet level but rather it stitches together two separate TCP (or UDP) flows and doesn't support IP protocols such as SCTP or other things that aren't TCP or UDP.
-* the standard WireGuard configuration doesn't support specifying DNS search domains, so resolving bare names like the `go` in `http://go/foo` won't work and you need to resolve names using the fully qualified `go.your-tailnet.ts.net` names.
-* since it's based on userspace tsnet mode, it doesn't pick up your system DNS configuration (yet?) and instead resolves non-tailnet DNS names using either your "Override DNS" tailnet settings for the global DNS resolver, or else defaults to `8.8.8.8` and `1.1.1.1` (using DoH) if that isn't set.
-
-## TODO
-
-* provisioning more than one low-powered device is possible, but requires manual config file edits. It should be possible to enroll multiple devices (including QR code support) easily.
-* incoming connections (from Tailscale to `lopower`) don't yet forward to the low-powered devices. When there's only one low-powered device, the mapping policy is obvious. When there are multiple, it's not as obvious. Maybe the answer is supporting [4via6 subnet routers](https://tailscale.com/kb/1201/4via6-subnets).
-
-## Installing
-
-* git clone this repo, switch to `lp` branch, `go install ./cmd/lopower` and see `lopower --help`.

cmd/lopower/lopower.go

@@ -1,872 +0,0 @@
-// The lopower server is a "Little Opinionated Proxy Over
-// Wireguard-Encrypted Route". It bridges a static WireGuard
-// client into a Tailscale network.
-package main
-
-import (
-	"bytes"
-	"context"
-	"encoding/base64"
-	"encoding/binary"
-	"encoding/hex"
-	"encoding/json"
-	"errors"
-	"flag"
-	"fmt"
-	"io"
-	"log"
-	"math/rand/v2"
-	"net"
-	"net/http"
-	"net/netip"
-	"os"
-	"os/signal"
-	"path/filepath"
-	"slices"
-	"strings"
-	"sync"
-	"sync/atomic"
-	"time"
-
-	"github.com/google/gopacket"
-	"github.com/google/gopacket/layers"
-	qrcode "github.com/skip2/go-qrcode"
-	"github.com/tailscale/wireguard-go/conn"
-	"github.com/tailscale/wireguard-go/device"
-	"github.com/tailscale/wireguard-go/tun"
-	"golang.org/x/net/dns/dnsmessage"
-	"golang.org/x/sys/unix"
-	"gvisor.dev/gvisor/pkg/buffer"
-	"gvisor.dev/gvisor/pkg/tcpip"
-	"gvisor.dev/gvisor/pkg/tcpip/adapters/gonet"
-	"gvisor.dev/gvisor/pkg/tcpip/link/channel"
-	"gvisor.dev/gvisor/pkg/tcpip/network/ipv4"
-	"gvisor.dev/gvisor/pkg/tcpip/network/ipv6"
-	"gvisor.dev/gvisor/pkg/tcpip/stack"
-	"gvisor.dev/gvisor/pkg/tcpip/transport/icmp"
-	"gvisor.dev/gvisor/pkg/tcpip/transport/tcp"
-	"gvisor.dev/gvisor/pkg/tcpip/transport/udp"
-	"gvisor.dev/gvisor/pkg/waiter"
-	"tailscale.com/net/packet"
-	"tailscale.com/net/tsaddr"
-	"tailscale.com/syncs"
-	"tailscale.com/tsnet"
-	"tailscale.com/types/dnstype"
-	"tailscale.com/types/ipproto"
-	"tailscale.com/types/key"
-	"tailscale.com/types/logger"
-	"tailscale.com/util/must"
-	"tailscale.com/wgengine/wgcfg"
-)
-
-var (
-	wgListenPort   = flag.Int("wg-port", 51820, "port number to listen on for WireGuard from the client")
-	confDir        = flag.String("dir", filepath.Join(os.Getenv("HOME"), ".config/lopower"), "directory to store configuration in")
-	wgPubHost      = flag.String("wg-host", "0.0.0.1", "IP address of lopower's WireGuard server that's accessible from the client")
-	qrListenAddr   = flag.String("qr-listen", "127.0.0.1:8014", "HTTP address to serve a QR code for client's WireGuard configuration, or empty for none")
-	printConfig    = flag.Bool("print-config", true, "print the client's WireGuard configuration to stdout on startup")
-	includeV4      = flag.Bool("include-v4", true, "include IPv4 (CGNAT) in the WireGuard configuration; incompatible with some carriers. IPv6 is always included.")
-	verbosePackets = flag.Bool("verbose-packets", false, "log packet contents")
-)
-
-type config struct {
-	PrivKey key.NodePrivate // the proxy server's key
-	Peers   []Peer
-
-	// V4 and V6 are the local IPs.
-	V4 netip.Addr
-	V6 netip.Addr
-
-	// CIDRs are used to allocate IPs to peers.
-	V4CIDR netip.Prefix
-	V6CIDR netip.Prefix
-}
-
-// IsLocalIP reports whether ip is one of the local IPs.
-func (c *config) IsLocalIP(ip netip.Addr) bool {
-	return ip.IsValid() && (ip == c.V4 || ip == c.V6)
-}
-
-type Peer struct {
-	PrivKey key.NodePrivate // e.g. proxy client's
-	V4      netip.Addr
-	V6      netip.Addr
-}
-
-func (lp *lpServer) storeConfigLocked() {
-	path := filepath.Join(lp.dir, "config.json")
-	if err := os.MkdirAll(filepath.Dir(path), 0700); err != nil {
-		log.Fatalf("os.MkdirAll(%q): %v", filepath.Dir(path), err)
-	}
-	f, err := os.OpenFile(path, os.O_CREATE|os.O_WRONLY|os.O_TRUNC, 0600)
-	if err != nil {
-		log.Fatalf("os.OpenFile(%q): %v", path, err)
-	}
-	defer f.Close()
-	must.Do(json.NewEncoder(f).Encode(lp.c))
-	if err := f.Close(); err != nil {
-		log.Fatalf("f.Close: %v", err)
-	}
-}
-
-func (lp *lpServer) loadConfig() {
-	path := filepath.Join(lp.dir, "config.json")
-	f, err := os.Open(path)
-	if err == nil {
-		defer f.Close()
-		var cfg *config
-		must.Do(json.NewDecoder(f).Decode(&cfg))
-		if len(cfg.Peers) > 0 { // as early version didn't set this
-			lp.mu.Lock()
-			defer lp.mu.Unlock()
-			lp.c = cfg
-		}
-		return
-	}
-	if !os.IsNotExist(err) {
-		log.Fatalf("os.OpenFile(%q): %v", path, err)
-	}
-	const defaultV4CIDR = "10.90.0.0/24"
-	const defaultV6CIDR = "fd7a:115c:a1e0:9909::/64" // 9909 = above QWERTY "LOPO"(wer)
-	c := &config{
-		PrivKey: key.NewNode(),
-		V4CIDR:  netip.MustParsePrefix(defaultV4CIDR),
-		V6CIDR:  netip.MustParsePrefix(defaultV6CIDR),
-	}
-	c.V4 = c.V4CIDR.Addr().Next()
-	c.V6 = c.V6CIDR.Addr().Next()
-	c.Peers = append(c.Peers, Peer{
-		PrivKey: key.NewNode(),
-		V4:      c.V4.Next(),
-		V6:      c.V6.Next(),
-	})
-
-	lp.mu.Lock()
-	defer lp.mu.Unlock()
-	lp.c = c
-	lp.storeConfigLocked()
-	return
-}
-
-func (lp *lpServer) reconfig() {
-	lp.mu.Lock()
-	wc := &wgcfg.Config{
-		Name:       "lopower0",
-		PrivateKey: lp.c.PrivKey,
-		ListenPort: uint16(*wgListenPort),
-		Addresses: []netip.Prefix{
-			netip.PrefixFrom(lp.c.V4, 32),
-			netip.PrefixFrom(lp.c.V6, 128),
-		},
-	}
-	for _, p := range lp.c.Peers {
-		wc.Peers = append(wc.Peers, wgcfg.Peer{
-			PublicKey: p.PrivKey.Public(),
-			AllowedIPs: []netip.Prefix{
-				netip.PrefixFrom(p.V4, 32),
-				netip.PrefixFrom(p.V6, 128),
-			},
-		})
-	}
-	lp.mu.Unlock()
-	must.Do(wgcfg.ReconfigDevice(lp.d, wc, log.Printf))
-}
-
-func newLP(ctx context.Context) *lpServer {
-	logf := log.Printf
-	deviceLogger := &device.Logger{
-		Verbosef: logger.Discard,
-		Errorf:   logf,
-	}
-	lp := &lpServer{
-		ctx:    ctx,
-		dir:    *confDir,
-		readCh: make(chan *stack.PacketBuffer, 16),
-	}
-	lp.loadConfig()
-	lp.initNetstack(ctx)
-	nst := &nsTUN{
-		lp:      lp,
-		closeCh: make(chan struct{}),
-		evChan:  make(chan tun.Event),
-	}
-
-	wgdev := wgcfg.NewDevice(nst, conn.NewDefaultBind(), deviceLogger)
-	lp.d = wgdev
-	must.Do(wgdev.Up())
-	lp.reconfig()
-
-	if *printConfig {
-		log.Printf("Device Wireguard config is:\n%s", lp.wgConfigForQR())
-	}
-
-	lp.startTSNet(ctx)
-	return lp
-}
-
-type lpServer struct {
-	dir    string
-	tsnet  *tsnet.Server
-	d      *device.Device
-	ns     *stack.Stack
-	ctx    context.Context // canceled on shutdown
-	linkEP *channel.Endpoint
-	readCh chan *stack.PacketBuffer // from gvisor/dns server => out to network
-
-	// protocolConns tracks the number of active connections for each connection.
-	// It is used to add and remove protocol addresses from netstack as needed.
-	protocolConns syncs.Map[tcpip.ProtocolAddress, *atomic.Int32]
-
-	mu sync.Mutex // protects following
-	c  *config
-}
-
-// MaxPacketSize is the maximum size (in bytes)
-// of a packet that can be injected into lpServer.
-const MaxPacketSize = device.MaxContentSize
-const nicID = 1
-
-func (lp *lpServer) initNetstack(ctx context.Context) error {
-	ns := stack.New(stack.Options{
-		NetworkProtocols: []stack.NetworkProtocolFactory{
-			ipv4.NewProtocol,
-			ipv6.NewProtocol,
-		},
-		TransportProtocols: []stack.TransportProtocolFactory{
-			tcp.NewProtocol,
-			icmp.NewProtocol4,
-			udp.NewProtocol,
-		},
-	})
-	lp.ns = ns
-	sackEnabledOpt := tcpip.TCPSACKEnabled(true) // TCP SACK is disabled by default
-	if tcpipErr := ns.SetTransportProtocolOption(tcp.ProtocolNumber, &sackEnabledOpt); tcpipErr != nil {
-		return fmt.Errorf("SetTransportProtocolOption SACK: %v", tcpipErr)
-	}
-	lp.linkEP = channel.New(512, 1280, "")
-	if tcpipProblem := ns.CreateNIC(nicID, lp.linkEP); tcpipProblem != nil {
-		return fmt.Errorf("CreateNIC: %v", tcpipProblem)
-	}
-	ns.SetPromiscuousMode(nicID, true)
-
-	lp.mu.Lock()
-	v4, v6 := lp.c.V4, lp.c.V6
-	lp.mu.Unlock()
-	prefix := tcpip.AddrFrom4Slice(v4.AsSlice()).WithPrefix()
-	if *includeV4 {
-		if tcpProb := ns.AddProtocolAddress(nicID, tcpip.ProtocolAddress{
-			Protocol:          ipv4.ProtocolNumber,
-			AddressWithPrefix: prefix,
-		}, stack.AddressProperties{}); tcpProb != nil {
-			return errors.New(tcpProb.String())
-		}
-	}
-	prefix = tcpip.AddrFrom16Slice(v6.AsSlice()).WithPrefix()
-	if tcpProb := ns.AddProtocolAddress(nicID, tcpip.ProtocolAddress{
-		Protocol:          ipv6.ProtocolNumber,
-		AddressWithPrefix: prefix,
-	}, stack.AddressProperties{}); tcpProb != nil {
-		return errors.New(tcpProb.String())
-	}
-
-	ipv4Subnet, err := tcpip.NewSubnet(tcpip.AddrFromSlice(make([]byte, 4)), tcpip.MaskFromBytes(make([]byte, 4)))
-	if err != nil {
-		return fmt.Errorf("could not create IPv4 subnet: %v", err)
-	}
-	ipv6Subnet, err := tcpip.NewSubnet(tcpip.AddrFromSlice(make([]byte, 16)), tcpip.MaskFromBytes(make([]byte, 16)))
-	if err != nil {
-		return fmt.Errorf("could not create IPv6 subnet: %v", err)
-	}
-
-	routes := []tcpip.Route{{
-		Destination: ipv4Subnet,
-		NIC:         nicID,
-	}, {
-		Destination: ipv6Subnet,
-		NIC:         nicID,
-	}}
-	if !*includeV4 {
-		routes = routes[1:]
-	}
-
-	ns.SetRouteTable(routes)
-
-	const tcpReceiveBufferSize = 0 // default
-	const maxInFlightConnectionAttempts = 8192
-	tcpFwd := tcp.NewForwarder(ns, tcpReceiveBufferSize, maxInFlightConnectionAttempts, lp.acceptTCP)
-	udpFwd := udp.NewForwarder(ns, lp.acceptUDP)
-	ns.SetTransportProtocolHandler(tcp.ProtocolNumber, func(tei stack.TransportEndpointID, pb *stack.PacketBuffer) (handled bool) {
-		return tcpFwd.HandlePacket(tei, pb)
-	})
-	ns.SetTransportProtocolHandler(udp.ProtocolNumber, func(tei stack.TransportEndpointID, pb *stack.PacketBuffer) (handled bool) {
-		return udpFwd.HandlePacket(tei, pb)
-	})
-
-	go func() {
-		for {
-			pkt := lp.linkEP.ReadContext(ctx)
-			if pkt == nil {
-				if ctx.Err() != nil {
-					// Return without logging.
-					log.Printf("linkEP.ReadContext: %v", ctx.Err())
-					return
-				}
-				continue
-			}
-			size := pkt.Size()
-			if size > MaxPacketSize || size == 0 {
-				pkt.DecRef()
-				continue
-			}
-			select {
-			case lp.readCh <- pkt:
-			case <-ctx.Done():
-			}
-		}
-	}()
-	return nil
-}
-
-func netaddrIPFromNetstackIP(s tcpip.Address) netip.Addr {
-	switch s.Len() {
-	case 4:
-		return netip.AddrFrom4(s.As4())
-	case 16:
-		return netip.AddrFrom16(s.As16()).Unmap()
-	}
-	return netip.Addr{}
-}
-
-func (lp *lpServer) trackProtocolAddr(destIP netip.Addr) (untrack func()) {
-	pa := tcpip.ProtocolAddress{
-		AddressWithPrefix: tcpip.AddrFromSlice(destIP.AsSlice()).WithPrefix(),
-	}
-	if destIP.Is4() {
-		pa.Protocol = ipv4.ProtocolNumber
-	} else if destIP.Is6() {
-		pa.Protocol = ipv6.ProtocolNumber
-	}
-
-	addrConns, _ := lp.protocolConns.LoadOrInit(pa, func() *atomic.Int32 { return new(atomic.Int32) })
-	if addrConns.Add(1) == 1 {
-		lp.ns.AddProtocolAddress(nicID, pa, stack.AddressProperties{
-			PEB:        stack.CanBePrimaryEndpoint, // zero value default
-			ConfigType: stack.AddressConfigStatic,  // zero value default
-		})
-	}
-	return func() {
-		if addrConns.Add(-1) == 0 {
-			lp.ns.RemoveAddress(nicID, pa.AddressWithPrefix.Address)
-		}
-	}
-}
-
-func (lp *lpServer) acceptUDP(r *udp.ForwarderRequest) {
-	log.Printf("acceptUDP: %v", r.ID())
-	destIP := netaddrIPFromNetstackIP(r.ID().LocalAddress)
-	untrack := lp.trackProtocolAddr(destIP)
-	var wq waiter.Queue
-	ep, udpErr := r.CreateEndpoint(&wq)
-	if udpErr != nil {
-		log.Printf("CreateEndpoint: %v", udpErr)
-		return
-	}
-	go func() {
-		defer untrack()
-		defer ep.Close()
-		reqDetails := r.ID()
-
-		clientRemoteIP := netaddrIPFromNetstackIP(reqDetails.RemoteAddress)
-		destPort := reqDetails.LocalPort
-		if !clientRemoteIP.IsValid() {
-			log.Printf("acceptUDP: invalid remote IP %v", reqDetails.RemoteAddress)
-			return
-		}
-
-		randPort := rand.IntN(65536-1024) + 1024
-		v4, v6 := lp.tsnet.TailscaleIPs()
-		var listenAddr netip.Addr
-		if destIP.Is4() {
-			listenAddr = v4
-		} else {
-			listenAddr = v6
-		}
-		backendConn, err := lp.tsnet.ListenPacket("udp", fmt.Sprintf("%s:%d", listenAddr, randPort))
-		if err != nil {
-			log.Printf("ListenPacket: %v", err)
-			return
-		}
-		defer backendConn.Close()
-		clientConn := gonet.NewUDPConn(&wq, ep)
-		defer clientConn.Close()
-		errCh := make(chan error, 2)
-		go func() (err error) {
-			defer func() { errCh <- err }()
-			var buf [64]byte
-			for {
-				n, _, err := backendConn.ReadFrom(buf[:])
-				if err != nil {
-					log.Printf("UDP read: %v", err)
-					return err
-				}
-				_, err = clientConn.Write(buf[:n])
-				if err != nil {
-					return err
-				}
-			}
-		}()
-		dstAddr, err := net.ResolveUDPAddr("udp", fmt.Sprintf("%s:%d", destIP, destPort))
-		if err != nil {
-			log.Printf("ResolveUDPAddr: %v", err)
-			return
-		}
-		go func() (err error) {
-			defer func() { errCh <- err }()
-			var buf [2048]byte
-			for {
-				n, err := clientConn.Read(buf[:])
-				if err != nil {
-					log.Printf("UDP read: %v", err)
-					return err
-				}
-				_, err = backendConn.WriteTo(buf[:n], dstAddr)
-				if err != nil {
-					return err
-				}
-			}
-		}()
-		err = <-errCh
-		if err != nil {
-			log.Printf("io.Copy: %v", err)
-		}
-	}()
-}
-
-func (lp *lpServer) acceptTCP(r *tcp.ForwarderRequest) {
-	log.Printf("acceptTCP: %v", r.ID())
-	reqDetails := r.ID()
-	destIP := netaddrIPFromNetstackIP(reqDetails.LocalAddress)
-	clientRemoteIP := netaddrIPFromNetstackIP(reqDetails.RemoteAddress)
-	destPort := reqDetails.LocalPort
-	if !clientRemoteIP.IsValid() {
-		log.Printf("acceptTCP: invalid remote IP %v", reqDetails.RemoteAddress)
-		r.Complete(true) // sends a RST
-		return
-	}
-	untrack := lp.trackProtocolAddr(destIP)
-	defer untrack()
-
-	var wq waiter.Queue
-	ep, tcpErr := r.CreateEndpoint(&wq)
-	if tcpErr != nil {
-		log.Printf("CreateEndpoint: %v", tcpErr)
-		r.Complete(true)
-		return
-	}
-	defer ep.Close()
-	ep.SocketOptions().SetKeepAlive(true)
-
-	if destPort == 53 && lp.c.IsLocalIP(destIP) {
-		tc := gonet.NewTCPConn(&wq, ep)
-		defer tc.Close()
-		r.Complete(false) // accept TCP connection
-		lp.handleTCPDNSQuery(tc, netip.AddrPortFrom(clientRemoteIP, reqDetails.RemotePort))
-		return
-	}
-
-	dialCtx, cancel := context.WithTimeout(context.Background(), 10*time.Second)
-	c, err := lp.tsnet.Dial(dialCtx, "tcp", fmt.Sprintf("%s:%d", destIP, destPort))
-	cancel()
-	if err != nil {
-		log.Printf("Dial(%s:%d): %v", destIP, destPort, err)
-		r.Complete(true) // sends a RST
-		return
-	}
-	defer c.Close()
-
-	tc := gonet.NewTCPConn(&wq, ep)
-	defer tc.Close()
-	r.Complete(false) // accept TCP connection
-
-	errc := make(chan error, 2)
-	go func() { _, err := io.Copy(tc, c); errc <- err }()
-	go func() { _, err := io.Copy(c, tc); errc <- err }()
-	err = <-errc
-	if err != nil {
-		log.Printf("io.Copy: %v", err)
-	}
-}
-
-func (lp *lpServer) wgConfigForQR() string {
-	var b strings.Builder
-
-	p := lp.c.Peers[0]
-	privHex, _ := p.PrivKey.MarshalText()
-	privHex = bytes.TrimPrefix(privHex, []byte("privkey:"))
-	priv := make([]byte, 32)
-	got, err := hex.Decode(priv, privHex)
-	if err != nil || got != 32 {
-		log.Printf("marshal text was: %q", privHex)
-		log.Fatalf("bad private key: %v, % bytes", err, got)
-	}
-	privb64 := base64.StdEncoding.EncodeToString(priv)
-
-	fmt.Fprintf(&b, "[Interface]\nPrivateKey = %s\n", privb64)
-	fmt.Fprintf(&b, "Address = %v,%v\n", p.V6, p.V4)
-
-	pubBin, _ := lp.c.PrivKey.Public().MarshalBinary()
-	if len(pubBin) != 34 {
-		log.Fatalf("bad pubkey length: %d", len(pubBin))
-	}
-	pubBin = pubBin[2:] // trim off "np"
-	pubb64 := base64.StdEncoding.EncodeToString(pubBin)
-
-	fmt.Fprintf(&b, "\n[Peer]\nPublicKey = %v\n", pubb64)
-	if *includeV4 {
-		fmt.Fprintf(&b, "AllowedIPs = %v/32,%v/128,%v,%v\n", lp.c.V4, lp.c.V6, tsaddr.TailscaleULARange(), tsaddr.CGNATRange())
-	} else {
-		fmt.Fprintf(&b, "AllowedIPs = %v/128,%v\n", lp.c.V6, tsaddr.TailscaleULARange())
-	}
-	fmt.Fprintf(&b, "Endpoint = %v\n", net.JoinHostPort(*wgPubHost, fmt.Sprint(*wgListenPort)))
-
-	return b.String()
-}
-
-func (lp *lpServer) serveQR() {
-	ln, err := net.Listen("tcp", *qrListenAddr)
-	if err != nil {
-		log.Fatalf("qr: %v", err)
-	}
-	log.Printf("# Serving QR code at http://%s/", ln.Addr())
-	hs := &http.Server{
-		Handler: http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
-			if r.URL.Path != "/" {
-				http.NotFound(w, r)
-				return
-			}
-			w.Header().Set("Content-Type", "image/png")
-			conf := lp.wgConfigForQR()
-			v, err := qrcode.Encode(conf, qrcode.Medium, 512)
-			if err != nil {
-				http.Error(w, err.Error(), http.StatusInternalServerError)
-				return
-			}
-			w.Write(v)
-		}),
-	}
-	if err := hs.Serve(ln); err != nil {
-		log.Fatalf("qr: %v", err)
-	}
-}
-
-type nsTUN struct {
-	lp      *lpServer
-	closeCh chan struct{}
-	evChan  chan tun.Event
-}
-
-func (t *nsTUN) File() *os.File {
-	panic("nsTUN.File() called, which makes no sense")
-}
-
-func (t *nsTUN) Close() error {
-	close(t.closeCh)
-	close(t.evChan)
-	return nil
-}
-
-// Read reads packets from gvisor (or the DNS server) to send out to the network.
-func (t *nsTUN) Read(out [][]byte, sizes []int, offset int) (int, error) {
-	select {
-	case <-t.closeCh:
-		return 0, io.EOF
-	case resPacket := <-t.lp.readCh:
-		defer resPacket.DecRef()
-		pkt := out[0][offset:]
-		n := copy(pkt, resPacket.NetworkHeader().Slice())
-		n += copy(pkt[n:], resPacket.TransportHeader().Slice())
-		n += copy(pkt[n:], resPacket.Data().AsRange().ToSlice())
-		if *verbosePackets {
-			log.Printf("[v] nsTUN.Read (out): % 02x", pkt[:n])
-		}
-		sizes[0] = n
-		return 1, nil
-	}
-}
-
-// Write accepts incoming packets. The packets begin at buffs[:][offset:],
-// like wireguard-go/tun.Device.Write. Write is called per-peer via
-// wireguard-go/device.Peer.RoutineSequentialReceiver, so it MUST be
-// thread-safe.
-func (t *nsTUN) Write(buffs [][]byte, offset int) (int, error) {
-	var pkt packet.Parsed
-	for _, buff := range buffs {
-		raw := buff[offset:]
-		pkt.Decode(raw)
-		packetBuf := stack.NewPacketBuffer(stack.PacketBufferOptions{
-			Payload: buffer.MakeWithData(slices.Clone(raw)),
-		})
-		if *verbosePackets {
-			log.Printf("[v] nsTUN.Write (in): % 02x", raw)
-		}
-		if pkt.IPProto == ipproto.UDP && pkt.Dst.Port() == 53 && t.lp.c.IsLocalIP(pkt.Dst.Addr()) {
-			// Handle DNS queries before sending to gvisor.
-			t.lp.handleDNSUDPQuery(raw)
-			continue
-		}
-		if pkt.IPVersion == 4 {
-			t.lp.linkEP.InjectInbound(ipv4.ProtocolNumber, packetBuf)
-		} else if pkt.IPVersion == 6 {
-			t.lp.linkEP.InjectInbound(ipv6.ProtocolNumber, packetBuf)
-		}
-	}
-	return len(buffs), nil
-}
-
-func (t *nsTUN) Flush() error             { return nil }
-func (t *nsTUN) MTU() (int, error)        { return 1500, nil }
-func (t *nsTUN) Name() (string, error)    { return "nstun", nil }
-func (t *nsTUN) Events() <-chan tun.Event { return t.evChan }
-func (t *nsTUN) BatchSize() int           { return 1 }
-
-func (lp *lpServer) startTSNet(ctx context.Context) {
-	hostname, err := os.Hostname()
-	if err != nil {
-		log.Fatal(err)
-	}
-
-	ts := &tsnet.Server{
-		Dir:       filepath.Join(lp.dir, "tsnet"),
-		Hostname:  hostname,
-		UserLogf:  log.Printf,
-		Ephemeral: false,
-	}
-	lp.tsnet = ts
-	ts.PreStart = func() error {
-		dnsMgr := ts.Sys().DNSManager.Get()
-		dnsMgr.SetForceAAAA(true)
-
-		// Force fallback resolvers to Google and Cloudflare as an ultimate
-		// fallback in case the Tailnet DNS servers are not set/forced. Normally
-		// tailscaled would resort to using the OS DNS resolvers, but
-		// tsnet/userspace binaries don't do that (yet?), so this is the
-		// "Opionated" part of the "LOPOWER" name. The opinion is just using
-		// big providers known to work. (Normally stock tailscaled never
-		// makes such opinions and never defaults to any big provider, unless
-		// you're already running on that big provider's network so have
-		// already indicated you're fine with them.))
-		dnsMgr.SetForceFallbackResolvers([]*dnstype.Resolver{
-			{Addr: "8.8.8.8"},
-			{Addr: "1.1.1.1"},
-		})
-		return nil
-	}
-
-	if _, err := ts.Up(ctx); err != nil {
-		log.Fatal(err)
-	}
-}
-
-// filteredDNSQuery wraps the MagicDNS server response but filters out A record responses
-// for *.ts.net if IPv4 is not enabled. This is so the e.g. a phone on a CGNAT-using
-// network doesn't prefer the "A" record over AAAA when dialing and dial into the
-// the carrier's CGNAT range into of the AAAA record into the Tailscale IPv6 ULA range.
-func (lp *lpServer) filteredDNSQuery(ctx context.Context, q []byte, family string, from netip.AddrPort) ([]byte, error) {
-	m, ok := lp.tsnet.Sys().DNSManager.GetOK()
-	if !ok {
-		return nil, errors.New("DNSManager not ready")
-	}
-	origRes, err := m.Query(ctx, q, family, from)
-	if err != nil {
-		return nil, err
-	}
-	if *includeV4 {
-		return origRes, nil
-	}
-
-	// Filter out *.ts.net A records.
-
-	var msg dnsmessage.Message
-	if err := msg.Unpack(origRes); err != nil {
-		return nil, err
-	}
-	newAnswers := msg.Answers[:0]
-	for _, a := range msg.Answers {
-		name := a.Header.Name.String()
-		if a.Header.Type == dnsmessage.TypeA && strings.HasSuffix(name, ".ts.net.") {
-			// Drop.
-			continue
-		}
-		newAnswers = append(newAnswers, a)
-	}
-
-	if len(newAnswers) == len(msg.Answers) {
-		// Nothing was filtered. No need to reencode it.
-		return origRes, nil
-	}
-
-	msg.Answers = newAnswers
-	return msg.Pack()
-}
-
-func (lp *lpServer) handleTCPDNSQuery(c net.Conn, src netip.AddrPort) {
-	defer c.Close()
-	var lenBuf [2]byte
-	for {
-		c.SetReadDeadline(time.Now().Add(30 * time.Second))
-		_, err := io.ReadFull(c, lenBuf[:])
-		if err != nil {
-			return
-		}
-		n := binary.BigEndian.Uint16(lenBuf[:])
-		buf := make([]byte, n)
-		c.SetReadDeadline(time.Now().Add(30 * time.Second))
-		_, err = io.ReadFull(c, buf[:])
-		if err != nil {
-			return
-		}
-		res, err := lp.filteredDNSQuery(context.Background(), buf, "tcp", src)
-		if err != nil {
-			log.Printf("TCP DNS query error: %v", err)
-			return
-		}
-		binary.BigEndian.PutUint16(lenBuf[:], uint16(len(res)))
-		c.SetWriteDeadline(time.Now().Add(30 * time.Second))
-		_, err = c.Write(lenBuf[:])
-		if err != nil {
-			return
-		}
-		c.SetWriteDeadline(time.Now().Add(30 * time.Second))
-		_, err = c.Write(res)
-		if err != nil {
-			return
-		}
-	}
-}
-
-// caller owns the raw memory.
-func (lp *lpServer) handleDNSUDPQuery(raw []byte) {
-	var pkt packet.Parsed
-	pkt.Decode(raw)
-	if pkt.IPProto != ipproto.UDP || pkt.Dst.Port() != 53 || !lp.c.IsLocalIP(pkt.Dst.Addr()) {
-		panic("caller error")
-	}
-
-	dnsRes, err := lp.filteredDNSQuery(context.Background(), pkt.Payload(), "udp", pkt.Src)
-	if err != nil {
-		log.Printf("DNS query error: %v", err)
-		return
-	}
-
-	ipLayer := mkIPLayer(layers.IPProtocolUDP, pkt.Dst.Addr(), pkt.Src.Addr())
-	udpLayer := &layers.UDP{
-		SrcPort: 53,
-		DstPort: layers.UDPPort(pkt.Src.Port()),
-	}
-
-	resPkt, err := mkPacket(ipLayer, udpLayer, gopacket.Payload(dnsRes))
-	if err != nil {
-		log.Printf("mkPacket: %v", err)
-		return
-	}
-	pktBuf := stack.NewPacketBuffer(stack.PacketBufferOptions{
-		Payload: buffer.MakeWithData(resPkt),
-	})
-	select {
-	case lp.readCh <- pktBuf:
-	case <-lp.ctx.Done():
-	}
-}
-
-type serializableNetworkLayer interface {
-	gopacket.SerializableLayer
-	gopacket.NetworkLayer
-}
-
-func mkIPLayer(proto layers.IPProtocol, src, dst netip.Addr) serializableNetworkLayer {
-	if src.Is4() {
-		return &layers.IPv4{
-			Protocol: proto,
-			SrcIP:    src.AsSlice(),
-			DstIP:    dst.AsSlice(),
-		}
-	}
-	if src.Is6() {
-		return &layers.IPv6{
-			NextHeader: proto,
-			SrcIP:      src.AsSlice(),
-			DstIP:      dst.AsSlice(),
-		}
-	}
-	panic("invalid src IP")
-}
-
-// mkPacket is a serializes a number of layers into a packet.
-//
-// It's a convenience wrapper around gopacket.SerializeLayers
-// that does some things automatically:
-//
-// * layers.IPv4/IPv6 Version is set to 4/6 if not already set
-// * layers.IPv4/IPv6 TTL/HopLimit is set to 64 if not already set
-// * the TCP/UDP/ICMPv6 checksum is set based on the network layer
-//
-// The provided layers in ll must be sorted from lowest (e.g. *layers.Ethernet)
-// to highest. (Depending on the need, the first layer will be either *layers.Ethernet
-// or *layers.IPv4/IPv6).
-func mkPacket(ll ...gopacket.SerializableLayer) ([]byte, error) {
-	var nl gopacket.NetworkLayer
-	for _, la := range ll {
-		switch la := la.(type) {
-		case *layers.IPv4:
-			nl = la
-			if la.Version == 0 {
-				la.Version = 4
-			}
-			if la.TTL == 0 {
-				la.TTL = 64
-			}
-		case *layers.IPv6:
-			nl = la
-			if la.Version == 0 {
-				la.Version = 6
-			}
-			if la.HopLimit == 0 {
-				la.HopLimit = 64
-			}
-		}
-	}
-	for _, la := range ll {
-		switch la := la.(type) {
-		case *layers.TCP:
-			la.SetNetworkLayerForChecksum(nl)
-		case *layers.UDP:
-			la.SetNetworkLayerForChecksum(nl)
-		case *layers.ICMPv6:
-			la.SetNetworkLayerForChecksum(nl)
-		}
-	}
-	buf := gopacket.NewSerializeBuffer()
-	opts := gopacket.SerializeOptions{FixLengths: true, ComputeChecksums: true}
-	if err := gopacket.SerializeLayers(buf, opts, ll...); err != nil {
-		return nil, fmt.Errorf("serializing packet: %v", err)
-	}
-	return buf.Bytes(), nil
-}
-
-func main() {
-	flag.Parse()
-	log.Printf("lopower starting")
-
-	ctx, cancel := context.WithCancel(context.Background())
-	defer cancel()
-
-	lp := newLP(ctx)
-
-	if *qrListenAddr != "" {
-		go lp.serveQR()
-	}
-
-	sigCh := make(chan os.Signal, 1)
-	signal.Notify(sigCh, unix.SIGTERM, os.Interrupt)
-	<-sigCh
-}

cmd/stunc/stunc.go

@@ -5,24 +5,40 @@
 package main
 
 import (
+	"flag"
 	"log"
 	"net"
 	"os"
 	"strconv"
+	"time"
 
 	"tailscale.com/net/stun"
 )
 
 func main() {
 	log.SetFlags(0)
-
-	if len(os.Args) < 2 || len(os.Args) > 3 {
-		log.Fatalf("usage: %s <hostname> [port]", os.Args[0])
-	}
-	host := os.Args[1]
+	var host string
 	port := "3478"
-	if len(os.Args) == 3 {
-		port = os.Args[2]
+
+	var readTimeout time.Duration
+	flag.DurationVar(&readTimeout, "timeout", 3*time.Second, "response wait timeout")
+
+	flag.Parse()
+
+	values := flag.Args()
+	if len(values) < 1 || len(values) > 2 {
+		log.Printf("usage: %s <hostname> [port]", os.Args[0])
+		flag.PrintDefaults()
+		os.Exit(1)
+	} else {
+		for i, value := range values {
+			switch i {
+			case 0:
+				host = value
+			case 1:
+				port = value
+			}
+		}
 	}
 	_, err := strconv.ParseUint(port, 10, 16)
 	if err != nil {
@@ -46,6 +62,10 @@ func main() {
 		log.Fatal(err)
 	}
 
+	err = c.SetReadDeadline(time.Now().Add(readTimeout))
+	if err != nil {
+		log.Fatal(err)
+	}
 	var buf [1024]byte
 	n, raddr, err := c.ReadFromUDPAddrPort(buf[:])
 	if err != nil {

cmd/stund/depaware.txt

@@ -8,12 +8,11 @@ tailscale.com/cmd/stund dependencies: (generated by github.com/tailscale/depawar
         github.com/go-json-experiment/json/internal/jsonopts         from github.com/go-json-experiment/json+
         github.com/go-json-experiment/json/internal/jsonwire         from github.com/go-json-experiment/json+
         github.com/go-json-experiment/json/jsontext                  from github.com/go-json-experiment/json+
-        github.com/google/uuid                                       from tailscale.com/util/fastuuid
+        github.com/munnerz/goautoneg                                 from github.com/prometheus/common/expfmt
      💣 github.com/prometheus/client_golang/prometheus               from tailscale.com/tsweb/promvarz
         github.com/prometheus/client_golang/prometheus/internal      from github.com/prometheus/client_golang/prometheus
         github.com/prometheus/client_model/go                        from github.com/prometheus/client_golang/prometheus+
         github.com/prometheus/common/expfmt                          from github.com/prometheus/client_golang/prometheus+
-        github.com/prometheus/common/internal/bitbucket.org/ww/goautoneg from github.com/prometheus/common/expfmt
         github.com/prometheus/common/model                           from github.com/prometheus/client_golang/prometheus+
   LD    github.com/prometheus/procfs                                 from github.com/prometheus/client_golang/prometheus
   LD    github.com/prometheus/procfs/internal/fs                     from github.com/prometheus/procfs
@@ -56,6 +55,7 @@ tailscale.com/cmd/stund dependencies: (generated by github.com/tailscale/depawar
         tailscale.com/net/stun                                       from tailscale.com/net/stunserver
         tailscale.com/net/stunserver                                 from tailscale.com/cmd/stund
         tailscale.com/net/tsaddr                                     from tailscale.com/tsweb
+        tailscale.com/syncs                                          from tailscale.com/metrics
         tailscale.com/tailcfg                                        from tailscale.com/version
         tailscale.com/tsweb                                          from tailscale.com/cmd/stund
         tailscale.com/tsweb/promvarz                                 from tailscale.com/tsweb
@@ -67,15 +67,17 @@ tailscale.com/cmd/stund dependencies: (generated by github.com/tailscale/depawar
         tailscale.com/types/logger                                   from tailscale.com/tsweb
         tailscale.com/types/opt                                      from tailscale.com/envknob+
         tailscale.com/types/ptr                                      from tailscale.com/tailcfg+
+        tailscale.com/types/result                                   from tailscale.com/util/lineiter
         tailscale.com/types/structs                                  from tailscale.com/tailcfg+
         tailscale.com/types/tkatype                                  from tailscale.com/tailcfg+
         tailscale.com/types/views                                    from tailscale.com/net/tsaddr+
         tailscale.com/util/ctxkey                                    from tailscale.com/tsweb+
    L 💣 tailscale.com/util/dirwalk                                   from tailscale.com/metrics
         tailscale.com/util/dnsname                                   from tailscale.com/tailcfg
-        tailscale.com/util/fastuuid                                  from tailscale.com/tsweb
-        tailscale.com/util/lineread                                  from tailscale.com/version/distro
+        tailscale.com/util/lineiter                                  from tailscale.com/version/distro
+        tailscale.com/util/mak                                       from tailscale.com/syncs
         tailscale.com/util/nocasemaps                                from tailscale.com/types/ipproto
+        tailscale.com/util/rands                                     from tailscale.com/tsweb
         tailscale.com/util/slicesx                                   from tailscale.com/tailcfg
         tailscale.com/util/vizerror                                  from tailscale.com/tailcfg+
         tailscale.com/version                                        from tailscale.com/envknob+
@@ -132,7 +134,6 @@ tailscale.com/cmd/stund dependencies: (generated by github.com/tailscale/depawar
         crypto/tls                                                   from net/http+
         crypto/x509                                                  from crypto/tls
         crypto/x509/pkix                                             from crypto/x509
-        database/sql/driver                                          from github.com/google/uuid
         embed                                                        from crypto/internal/nistec+
         encoding                                                     from encoding/json+
         encoding/asn1                                                from crypto/x509+
@@ -154,7 +155,6 @@ tailscale.com/cmd/stund dependencies: (generated by github.com/tailscale/depawar
         html                                                         from net/http/pprof+
         io                                                           from bufio+
         io/fs                                                        from crypto/x509+
-        io/ioutil                                                    from google.golang.org/protobuf/internal/impl
         iter                                                         from maps+
         log                                                          from expvar+
         log/internal                                                 from log
@@ -163,7 +163,7 @@ tailscale.com/cmd/stund dependencies: (generated by github.com/tailscale/depawar
         math/big                                                     from crypto/dsa+
         math/bits                                                    from compress/flate+
         math/rand                                                    from math/big+
-        math/rand/v2                                                 from tailscale.com/util/fastuuid+
+        math/rand/v2                                                 from internal/concurrent+
         mime                                                         from github.com/prometheus/common/expfmt+
         mime/multipart                                               from net/http
         mime/quotedprintable                                         from mime/multipart