VERSION.txt: this is v1.80.2 (#15003)

Signed-off-by: Andrea Gottardo <andrea@gottardo.me>

.github/workflows/checklocks.yml

@@ -18,7 +18,7 @@ jobs:
     runs-on: [ ubuntu-latest ]
     steps:
       - name: Check out code
-        uses: actions/checkout@692973e3d937129bcbf40652eb9f2f61becf3332 # v4.1.7
+        uses: actions/checkout@11bd71901bbe5b1630ceea73d27597364c9af683 # v4.2.2
 
       - name: Build checklocks
         run: ./tool/go build -o /tmp/checklocks gvisor.dev/gvisor/tools/checklocks/cmd/checklocks

.github/workflows/codeql-analysis.yml

@@ -45,17 +45,17 @@ jobs:
 
     steps:
     - name: Checkout repository
-      uses: actions/checkout@692973e3d937129bcbf40652eb9f2f61becf3332 # v4.1.7
+      uses: actions/checkout@11bd71901bbe5b1630ceea73d27597364c9af683 # v4.2.2
 
     # Install a more recent Go that understands modern go.mod content.
     - name: Install Go
-      uses: actions/setup-go@41dfa10bad2bb2ae585af6ee5bb4d7d973ad74ed # v5.1.0
+      uses: actions/setup-go@f111f3307d8850f501ac008e886eec1fd1932a34 # v5.3.0
       with:
         go-version-file: go.mod
 
     # Initializes the CodeQL tools for scanning.
     - name: Initialize CodeQL
-      uses: github/codeql-action/init@aa578102511db1f4524ed59b8cc2bae4f6e88195 # v3.27.6
+      uses: github/codeql-action/init@f6091c0113d1dcf9b98e269ee48e8a7e51b7bdd4 # v3.28.5
       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@aa578102511db1f4524ed59b8cc2bae4f6e88195 # v3.27.6
+      uses: github/codeql-action/autobuild@f6091c0113d1dcf9b98e269ee48e8a7e51b7bdd4 # v3.28.5
 
     # 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@aa578102511db1f4524ed59b8cc2bae4f6e88195 # v3.27.6
+      uses: github/codeql-action/analyze@f6091c0113d1dcf9b98e269ee48e8a7e51b7bdd4 # v3.28.5

.github/workflows/docker-file-build.yml

@@ -10,6 +10,6 @@ jobs:
   deploy:
     runs-on: ubuntu-latest
     steps:
-    - uses: actions/checkout@692973e3d937129bcbf40652eb9f2f61becf3332 # v4.1.7
+    - uses: actions/checkout@11bd71901bbe5b1630ceea73d27597364c9af683 # v4.2.2
     - name: "Build Docker image"
       run: docker build .

.github/workflows/flakehub-publish-tagged.yml

@@ -17,7 +17,7 @@ jobs:
       id-token: "write"
       contents: "read"
     steps:
-      - uses: actions/checkout@692973e3d937129bcbf40652eb9f2f61becf3332 # v4.1.7
+      - uses: actions/checkout@11bd71901bbe5b1630ceea73d27597364c9af683 # v4.2.2
         with:
           ref: "${{ (inputs.tag != null) && format('refs/tags/{0}', inputs.tag) || '' }}"
       - uses: "DeterminateSystems/nix-installer-action@main"

.github/workflows/golangci-lint.yml

@@ -23,16 +23,15 @@ jobs:
     name: lint
     runs-on: ubuntu-latest
     steps:
-      - uses: actions/checkout@692973e3d937129bcbf40652eb9f2f61becf3332 # v4.1.7
+      - uses: actions/checkout@11bd71901bbe5b1630ceea73d27597364c9af683 # v4.2.2
 
-      - uses: actions/setup-go@41dfa10bad2bb2ae585af6ee5bb4d7d973ad74ed # v5.1.0
+      - uses: actions/setup-go@f111f3307d8850f501ac008e886eec1fd1932a34 # v5.3.0
         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

@@ -14,7 +14,7 @@ jobs:
 
     steps:
       - name: Check out code into the Go module directory
-        uses: actions/checkout@692973e3d937129bcbf40652eb9f2f61becf3332 # v4.1.7
+        uses: actions/checkout@11bd71901bbe5b1630ceea73d27597364c9af683 # v4.2.2
 
       - name: Install govulncheck
         run: ./tool/go install golang.org/x/vuln/cmd/govulncheck@latest
@@ -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:
@@ -29,13 +31,11 @@ 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"
           - "parrotsec/core:latest"
           - "kalilinux/kali-rolling"
           - "kalilinux/kali-dev"
@@ -48,7 +48,7 @@ jobs:
           - "opensuse/leap:latest"
           - "opensuse/tumbleweed:latest"
           - "archlinux:latest"
-          - "alpine:3.14"
+          - "alpine:3.21"
           - "alpine:latest"
           - "alpine:edge"
         deps:
@@ -58,10 +58,6 @@ 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 }}
@@ -95,10 +91,7 @@ jobs:
         || contains(matrix.image, 'parrotsec')
         || contains(matrix.image, 'kalilinux')
     - name: checkout
-      # We cannot use v4, as it requires a newer glibc version than some of the
-      # tested images provide. See
-      # https://github.com/actions/checkout/issues/1487
-      uses: actions/checkout@f43a0e5ff2bd294095638e18286ca9a3d1956744 # v3.6.0
+      uses: actions/checkout@11bd71901bbe5b1630ceea73d27597364c9af683 # v4.2.2
     - name: run installer
       run: scripts/installer.sh
       # Package installation can fail in docker because systemd is not running

.github/workflows/kubemanifests.yaml

@@ -17,7 +17,7 @@ jobs:
     runs-on: [ ubuntu-latest ]
     steps:
     - name: Check out code
-      uses: actions/checkout@692973e3d937129bcbf40652eb9f2f61becf3332 # v4.1.7
+      uses: actions/checkout@11bd71901bbe5b1630ceea73d27597364c9af683 # v4.2.2
     - name: Build and lint Helm chart
       run: |
         eval `./tool/go run ./cmd/mkversion`

.github/workflows/ssh-integrationtest.yml

@@ -17,7 +17,7 @@ jobs:
     runs-on: ubuntu-latest
     steps:
       - name: Check out code
-        uses: actions/checkout@692973e3d937129bcbf40652eb9f2f61becf3332 # v4.1.7
+        uses: actions/checkout@11bd71901bbe5b1630ceea73d27597364c9af683 # v4.2.2
       - name: Run SSH integration tests
         run: |
           make sshintegrationtest

.github/workflows/test.yml

@@ -50,7 +50,7 @@ jobs:
           - shard: '4/4'
     steps:
     - name: checkout
-      uses: actions/checkout@692973e3d937129bcbf40652eb9f2f61becf3332 # v4.1.7
+      uses: actions/checkout@11bd71901bbe5b1630ceea73d27597364c9af683 # v4.2.2
     - name: build test wrapper
       run: ./tool/go build -o /tmp/testwrapper ./cmd/testwrapper
     - name: integration tests as root
@@ -78,7 +78,7 @@ jobs:
     runs-on: ubuntu-22.04
     steps:
     - name: checkout
-      uses: actions/checkout@692973e3d937129bcbf40652eb9f2f61becf3332 # v4.1.7
+      uses: actions/checkout@11bd71901bbe5b1630ceea73d27597364c9af683 # v4.2.2
     - name: Restore Cache
       uses: actions/cache@1bd1e32a3bdc45362d1e726936510720a7c30a57 # v4.2.0
       with:
@@ -150,10 +150,10 @@ jobs:
     runs-on: windows-2022
     steps:
     - name: checkout
-      uses: actions/checkout@692973e3d937129bcbf40652eb9f2f61becf3332 # v4.1.7
+      uses: actions/checkout@11bd71901bbe5b1630ceea73d27597364c9af683 # v4.2.2
 
     - name: Install Go
-      uses: actions/setup-go@41dfa10bad2bb2ae585af6ee5bb4d7d973ad74ed # v5.1.0
+      uses: actions/setup-go@f111f3307d8850f501ac008e886eec1fd1932a34 # v5.3.0
       with:
         go-version-file: go.mod
         cache: false
@@ -190,7 +190,7 @@ jobs:
       options: --privileged
     steps:
     - name: checkout
-      uses: actions/checkout@692973e3d937129bcbf40652eb9f2f61becf3332 # v4.1.7
+      uses: actions/checkout@11bd71901bbe5b1630ceea73d27597364c9af683 # v4.2.2
     - name: chown
       run: chown -R $(id -u):$(id -g) $PWD
     - name: privileged tests
@@ -202,7 +202,7 @@ jobs:
     if: github.repository == 'tailscale/tailscale'
     steps:
     - name: checkout
-      uses: actions/checkout@692973e3d937129bcbf40652eb9f2f61becf3332 # v4.1.7
+      uses: actions/checkout@11bd71901bbe5b1630ceea73d27597364c9af683 # v4.2.2
     - name: Run VM tests
       run: ./tool/go test ./tstest/integration/vms -v -no-s3 -run-vm-tests -run=TestRunUbuntu2004
       env:
@@ -214,7 +214,7 @@ jobs:
     runs-on: ubuntu-22.04
     steps:
     - name: checkout
-      uses: actions/checkout@692973e3d937129bcbf40652eb9f2f61becf3332 # v4.1.7
+      uses: actions/checkout@11bd71901bbe5b1630ceea73d27597364c9af683 # v4.2.2
     - name: build all
       run: ./tool/go install -race ./cmd/...
     - name: build tests
@@ -258,7 +258,7 @@ jobs:
     runs-on: ubuntu-22.04
     steps:
     - name: checkout
-      uses: actions/checkout@692973e3d937129bcbf40652eb9f2f61becf3332 # v4.1.7
+      uses: actions/checkout@11bd71901bbe5b1630ceea73d27597364c9af683 # v4.2.2
     - name: Restore Cache
       uses: actions/cache@1bd1e32a3bdc45362d1e726936510720a7c30a57 # v4.2.0
       with:
@@ -295,7 +295,7 @@ jobs:
     runs-on: ubuntu-22.04
     steps:
     - name: checkout
-      uses: actions/checkout@692973e3d937129bcbf40652eb9f2f61becf3332 # v4.1.7
+      uses: actions/checkout@11bd71901bbe5b1630ceea73d27597364c9af683 # v4.2.2
     - name: build some
       run: ./tool/go build ./ipn/... ./wgengine/ ./types/... ./control/controlclient
       env:
@@ -313,11 +313,17 @@ 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
+      uses: actions/checkout@11bd71901bbe5b1630ceea73d27597364c9af683 # v4.2.2
     - name: Restore Cache
       uses: actions/cache@1bd1e32a3bdc45362d1e726936510720a7c30a57 # v4.2.0
       with:
@@ -350,7 +356,7 @@ jobs:
     runs-on: ubuntu-22.04
     steps:
     - name: checkout
-      uses: actions/checkout@692973e3d937129bcbf40652eb9f2f61becf3332 # v4.1.7
+      uses: actions/checkout@11bd71901bbe5b1630ceea73d27597364c9af683 # v4.2.2
       # Super minimal Android build that doesn't even use CGO and doesn't build everything that's needed
       # and is only arm64. But it's a smoke build: it's not meant to catch everything. But it'll catch
       # some Android breakages early.
@@ -365,7 +371,7 @@ jobs:
     runs-on: ubuntu-22.04
     steps:
     - name: checkout
-      uses: actions/checkout@692973e3d937129bcbf40652eb9f2f61becf3332 # v4.1.7
+      uses: actions/checkout@11bd71901bbe5b1630ceea73d27597364c9af683 # v4.2.2
     - name: Restore Cache
       uses: actions/cache@1bd1e32a3bdc45362d1e726936510720a7c30a57 # v4.2.0
       with:
@@ -399,7 +405,7 @@ jobs:
     runs-on: ubuntu-22.04
     steps:
     - name: checkout
-      uses: actions/checkout@692973e3d937129bcbf40652eb9f2f61becf3332 # v4.1.7
+      uses: actions/checkout@11bd71901bbe5b1630ceea73d27597364c9af683 # v4.2.2
     - name: test tailscale_go
       run: ./tool/go test -tags=tailscale_go,ts_enable_sockstats ./net/sockstats/...
 
@@ -461,7 +467,7 @@ jobs:
       run: |
         echo "artifacts_path=$(realpath .)" >> $GITHUB_ENV
     - name: upload crash
-      uses: actions/upload-artifact@b4b15b8c7c6ac21ea08fcf65892d2ee8f75cf882 # v4.4.3
+      uses: actions/upload-artifact@65c4c4a1ddee5b72f698fdd19549f0f0fb45cf08 # v4.6.0
       if: steps.run.outcome != 'success' && steps.build.outcome == 'success'
       with:
         name: artifacts
@@ -471,17 +477,17 @@ jobs:
     runs-on: ubuntu-22.04
     steps:
     - name: checkout
-      uses: actions/checkout@692973e3d937129bcbf40652eb9f2f61becf3332 # v4.1.7
+      uses: actions/checkout@11bd71901bbe5b1630ceea73d27597364c9af683 # v4.2.2
     - name: check depaware
       run: |
         export PATH=$(./tool/go env GOROOT)/bin:$PATH
-        find . -name 'depaware.txt' | xargs -n1 dirname | xargs ./tool/go run github.com/tailscale/depaware --check
+        find . -name 'depaware.txt' | xargs -n1 dirname | xargs ./tool/go run github.com/tailscale/depaware --check --internal
 
   go_generate:
     runs-on: ubuntu-22.04
     steps:
     - name: checkout
-      uses: actions/checkout@692973e3d937129bcbf40652eb9f2f61becf3332 # v4.1.7
+      uses: actions/checkout@11bd71901bbe5b1630ceea73d27597364c9af683 # v4.2.2
     - name: check that 'go generate' is clean
       run: |
         pkgs=$(./tool/go list ./... | grep -Ev 'dnsfallback|k8s-operator|xdp')
@@ -494,7 +500,7 @@ jobs:
     runs-on: ubuntu-22.04
     steps:
     - name: checkout
-      uses: actions/checkout@692973e3d937129bcbf40652eb9f2f61becf3332 # v4.1.7
+      uses: actions/checkout@11bd71901bbe5b1630ceea73d27597364c9af683 # v4.2.2
     - name: check that 'go mod tidy' is clean
       run: |
         ./tool/go mod tidy
@@ -506,7 +512,7 @@ jobs:
     runs-on: ubuntu-22.04
     steps:
     - name: checkout
-      uses: actions/checkout@692973e3d937129bcbf40652eb9f2f61becf3332 # v4.1.7
+      uses: actions/checkout@11bd71901bbe5b1630ceea73d27597364c9af683 # v4.2.2
     - name: check licenses
       run: ./scripts/check_license_headers.sh .
 
@@ -522,7 +528,7 @@ jobs:
             goarch: "386"
     steps:
     - name: checkout
-      uses: actions/checkout@692973e3d937129bcbf40652eb9f2f61becf3332 # v4.1.7
+      uses: actions/checkout@11bd71901bbe5b1630ceea73d27597364c9af683 # v4.2.2
     - name: install staticcheck
       run: GOBIN=~/.local/bin ./tool/go install honnef.co/go/tools/cmd/staticcheck
     - name: run staticcheck
@@ -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

@@ -21,7 +21,7 @@ jobs:
 
     steps:
       - name: Check out code
-        uses: actions/checkout@692973e3d937129bcbf40652eb9f2f61becf3332 # v4.1.7
+        uses: actions/checkout@11bd71901bbe5b1630ceea73d27597364c9af683 # v4.2.2
 
       - name: Run update-flakes
         run: ./update-flake.sh
@@ -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

@@ -14,7 +14,7 @@ jobs:
 
     steps:
       - name: Check out code
-        uses: actions/checkout@692973e3d937129bcbf40652eb9f2f61becf3332 # v4.1.7
+        uses: actions/checkout@11bd71901bbe5b1630ceea73d27597364c9af683 # v4.2.2
 
       - name: Run go get
         run: |
@@ -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>

.github/workflows/webclient.yml

@@ -24,7 +24,7 @@ jobs:
 
     steps:
       - name: Check out code
-        uses: actions/checkout@692973e3d937129bcbf40652eb9f2f61becf3332 # v4.1.7
+        uses: actions/checkout@11bd71901bbe5b1630ceea73d27597364c9af683 # v4.2.2
       - name: Install deps
         run: ./tool/yarn --cwd client/web
       - name: Run lint

Makefile

@@ -17,7 +17,7 @@ lint: ## Run golangci-lint
 updatedeps: ## Update depaware deps
 	# depaware (via x/tools/go/packages) shells back to "go", so make sure the "go"
 	# it finds in its $$PATH is the right one.
-	PATH="$$(./tool/go env GOROOT)/bin:$$PATH" ./tool/go run github.com/tailscale/depaware --update \
+	PATH="$$(./tool/go env GOROOT)/bin:$$PATH" ./tool/go run github.com/tailscale/depaware --update --internal \
 		tailscale.com/cmd/tailscaled \
 		tailscale.com/cmd/tailscale \
 		tailscale.com/cmd/derper \
@@ -27,7 +27,7 @@ updatedeps: ## Update depaware deps
 depaware: ## Run depaware checks
 	# depaware (via x/tools/go/packages) shells back to "go", so make sure the "go"
 	# it finds in its $$PATH is the right one.
-	PATH="$$(./tool/go env GOROOT)/bin:$$PATH" ./tool/go run github.com/tailscale/depaware --check \
+	PATH="$$(./tool/go env GOROOT)/bin:$$PATH" ./tool/go run github.com/tailscale/depaware --check --internal \
 		tailscale.com/cmd/tailscaled \
 		tailscale.com/cmd/tailscale \
 		tailscale.com/cmd/derper \

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 @@
-1.79.0
+1.80.2

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,ts_omit_capture"
 		;;
 	--box)
 		shift

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 {

client/web/src/components/views/login-view.tsx

@@ -1,13 +1,11 @@
 // Copyright (c) Tailscale Inc & AUTHORS
 // SPDX-License-Identifier: BSD-3-Clause
 
-import React, { useState } from "react"
+import React from "react"
 import { useAPI } from "src/api"
 import TailscaleIcon from "src/assets/icons/tailscale-icon.svg?react"
 import { NodeData } from "src/types"
 import Button from "src/ui/button"
-import Collapsible from "src/ui/collapsible"
-import Input from "src/ui/input"
 
 /**
  * LoginView is rendered when the client is not authenticated
@@ -15,8 +13,6 @@ import Input from "src/ui/input"
  */
 export default function LoginView({ data }: { data: NodeData }) {
   const api = useAPI()
-  const [controlURL, setControlURL] = useState<string>("")
-  const [authKey, setAuthKey] = useState<string>("")
 
   return (
     <div className="mb-8 py-6 px-8 bg-white rounded-md shadow-2xl">
@@ -88,8 +84,6 @@ export default function LoginView({ data }: { data: NodeData }) {
                 action: "up",
                 data: {
                   Reauthenticate: true,
-                  ControlURL: controlURL,
-                  AuthKey: authKey,
                 },
               })
             }
@@ -98,34 +92,6 @@ export default function LoginView({ data }: { data: NodeData }) {
           >
             Log In
           </Button>
-          <Collapsible trigger="Advanced options">
-            <h4 className="font-medium mb-1 mt-2">Auth Key</h4>
-            <p className="text-sm text-gray-500">
-              Connect with a pre-authenticated key.{" "}
-              <a
-                href="https://tailscale.com/kb/1085/auth-keys/"
-                className="link"
-                target="_blank"
-                rel="noreferrer"
-              >
-                Learn more &rarr;
-              </a>
-            </p>
-            <Input
-              className="mt-2"
-              value={authKey}
-              onChange={(e) => setAuthKey(e.target.value)}
-              placeholder="tskey-auth-XXX"
-            />
-            <h4 className="font-medium mt-3 mb-1">Server URL</h4>
-            <p className="text-sm text-gray-500">Base URL of control server.</p>
-            <Input
-              className="mt-2"
-              value={controlURL}
-              onChange={(e) => setControlURL(e.target.value)}
-              placeholder="https://login.tailscale.com/"
-            />
-          </Collapsible>
         </>
       )}
     </div>

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"
 )
 
@@ -211,15 +211,25 @@ func NewServer(opts ServerOpts) (s *Server, err error) {
 	// The client is secured by limiting the interface it listens on,
 	// or by authenticating requests before they reach the web client.
 	csrfProtect := csrf.Protect(s.csrfKey(), csrf.Secure(false))
+
+	// signal to the CSRF middleware that the request is being served over
+	// plaintext HTTP to skip TLS-only header checks.
+	withSetPlaintext := func(h http.Handler) http.Handler {
+		return http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+			r = csrf.PlaintextHTTPRequest(r)
+			h.ServeHTTP(w, r)
+		})
+	}
+
 	switch s.mode {
 	case LoginServerMode:
-		s.apiHandler = csrfProtect(http.HandlerFunc(s.serveLoginAPI))
+		s.apiHandler = csrfProtect(withSetPlaintext(http.HandlerFunc(s.serveLoginAPI)))
 		metric = "web_login_client_initialization"
 	case ReadOnlyServerMode:
-		s.apiHandler = csrfProtect(http.HandlerFunc(s.serveLoginAPI))
+		s.apiHandler = csrfProtect(withSetPlaintext(http.HandlerFunc(s.serveLoginAPI)))
 		metric = "web_readonly_client_initialization"
 	case ManageServerMode:
-		s.apiHandler = csrfProtect(http.HandlerFunc(s.serveAPI))
+		s.apiHandler = csrfProtect(withSetPlaintext(http.HandlerFunc(s.serveAPI)))
 		metric = "web_client_initialization"
 	}
 
@@ -695,16 +705,16 @@ 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 +814,8 @@ 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 +874,14 @@ 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 +901,6 @@ 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/containerboot/healthz.go

@@ -6,9 +6,12 @@
 package main
 
 import (
+	"fmt"
 	"log"
 	"net/http"
 	"sync"
+
+	"tailscale.com/kube/kubetypes"
 )
 
 // healthz is a simple health check server, if enabled it returns 200 OK if
@@ -17,6 +20,7 @@ import (
 type healthz struct {
 	sync.Mutex
 	hasAddrs bool
+	podIPv4  string
 }
 
 func (h *healthz) ServeHTTP(w http.ResponseWriter, r *http.Request) {
@@ -24,7 +28,10 @@ func (h *healthz) ServeHTTP(w http.ResponseWriter, r *http.Request) {
 	defer h.Unlock()
 
 	if h.hasAddrs {
-		w.Write([]byte("ok"))
+		w.Header().Add(kubetypes.PodIPv4Header, h.podIPv4)
+		if _, err := w.Write([]byte("ok")); err != nil {
+			http.Error(w, fmt.Sprintf("error writing status: %v", err), http.StatusInternalServerError)
+		}
 	} else {
 		http.Error(w, "node currently has no tailscale IPs", http.StatusServiceUnavailable)
 	}
@@ -43,8 +50,8 @@ func (h *healthz) update(healthy bool) {
 // 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 healthHandlers(mux *http.ServeMux) *healthz {
-	h := &healthz{}
+func healthHandlers(mux *http.ServeMux, podIPv4 string) *healthz {
+	h := &healthz{podIPv4: podIPv4}
 	mux.Handle("GET /healthz", h)
 	return h
 }

cmd/containerboot/kube.go

@@ -8,15 +8,22 @@ package main
 import (
 	"context"
 	"encoding/json"
+	"errors"
 	"fmt"
+	"log"
 	"net/http"
 	"net/netip"
 	"os"
+	"strings"
+	"time"
 
+	"tailscale.com/ipn"
 	"tailscale.com/kube/kubeapi"
 	"tailscale.com/kube/kubeclient"
 	"tailscale.com/kube/kubetypes"
+	"tailscale.com/logtail/backoff"
 	"tailscale.com/tailcfg"
+	"tailscale.com/types/logger"
 )
 
 // kubeClient is a wrapper around Tailscale's internal kube client that knows how to talk to the kube API server. We use
@@ -126,3 +133,62 @@ func (kc *kubeClient) storeCapVerUID(ctx context.Context, podUID string) error {
 	}
 	return kc.StrategicMergePatchSecret(ctx, kc.stateSecret, s, "tailscale-container")
 }
+
+// waitForConsistentState waits for tailscaled to finish writing state if it
+// looks like it's started. It is designed to reduce the likelihood that
+// tailscaled gets shut down in the window between authenticating to control
+// and finishing writing state. However, it's not bullet proof because we can't
+// atomically authenticate and write state.
+func (kc *kubeClient) waitForConsistentState(ctx context.Context) error {
+	var logged bool
+
+	bo := backoff.NewBackoff("", logger.Discard, 2*time.Second)
+	for {
+		select {
+		case <-ctx.Done():
+			return ctx.Err()
+		default:
+		}
+		secret, err := kc.GetSecret(ctx, kc.stateSecret)
+		if ctx.Err() != nil || kubeclient.IsNotFoundErr(err) {
+			return nil
+		}
+		if err != nil {
+			return fmt.Errorf("getting Secret %q: %v", kc.stateSecret, err)
+		}
+
+		if hasConsistentState(secret.Data) {
+			return nil
+		}
+
+		if !logged {
+			log.Printf("Waiting for tailscaled to finish writing state to Secret %q", kc.stateSecret)
+			logged = true
+		}
+		bo.BackOff(ctx, errors.New("")) // Fake error to trigger actual sleep.
+	}
+}
+
+// hasConsistentState returns true is there is either no state or the full set
+// of expected keys are present.
+func hasConsistentState(d map[string][]byte) bool {
+	var (
+		_, hasCurrent = d[string(ipn.CurrentProfileStateKey)]
+		_, hasKnown   = d[string(ipn.KnownProfilesStateKey)]
+		_, hasMachine = d[string(ipn.MachineKeyStateKey)]
+		hasProfile    bool
+	)
+
+	for k := range d {
+		if strings.HasPrefix(k, "profile-") {
+			if hasProfile {
+				return false // We only expect one profile.
+			}
+			hasProfile = true
+		}
+	}
+
+	// Approximate check, we don't want to reimplement all of profileManager.
+	return (hasCurrent && hasKnown && hasMachine && hasProfile) ||
+		(!hasCurrent && !hasKnown && !hasMachine && !hasProfile)
+}

cmd/containerboot/kube_test.go

@@ -9,8 +9,10 @@ import (
 	"context"
 	"errors"
 	"testing"
+	"time"
 
 	"github.com/google/go-cmp/cmp"
+	"tailscale.com/ipn"
 	"tailscale.com/kube/kubeapi"
 	"tailscale.com/kube/kubeclient"
 )
@@ -205,3 +207,34 @@ func TestSetupKube(t *testing.T) {
 		})
 	}
 }
+
+func TestWaitForConsistentState(t *testing.T) {
+	data := map[string][]byte{
+		// Missing _current-profile.
+		string(ipn.KnownProfilesStateKey): []byte(""),
+		string(ipn.MachineKeyStateKey):    []byte(""),
+		"profile-foo":                     []byte(""),
+	}
+	kc := &kubeClient{
+		Client: &kubeclient.FakeClient{
+			GetSecretImpl: func(context.Context, string) (*kubeapi.Secret, error) {
+				return &kubeapi.Secret{
+					Data: data,
+				}, nil
+			},
+		},
+	}
+
+	ctx, cancel := context.WithTimeout(context.Background(), time.Second)
+	defer cancel()
+	if err := kc.waitForConsistentState(ctx); err != context.DeadlineExceeded {
+		t.Fatalf("expected DeadlineExceeded, got %v", err)
+	}
+
+	ctx, cancel = context.WithTimeout(context.Background(), time.Second)
+	defer cancel()
+	data[string(ipn.CurrentProfileStateKey)] = []byte("")
+	if err := kc.waitForConsistentState(ctx); err != nil {
+		t.Fatalf("expected nil, got %v", err)
+	}
+}

cmd/containerboot/main.go

@@ -137,53 +137,83 @@ func newNetfilterRunner(logf logger.Logf) (linuxfw.NetfilterRunner, error) {
 }
 
 func main() {
+	if err := run(); err != nil && !errors.Is(err, context.Canceled) {
+		log.Fatal(err)
+	}
+}
+
+func run() error {
 	log.SetPrefix("boot: ")
 	tailscale.I_Acknowledge_This_API_Is_Unstable = true
 
 	cfg, err := configFromEnv()
 	if err != nil {
-		log.Fatalf("invalid configuration: %v", err)
+		return fmt.Errorf("invalid configuration: %w", err)
 	}
 
 	if !cfg.UserspaceMode {
 		if err := ensureTunFile(cfg.Root); err != nil {
-			log.Fatalf("Unable to create tuntap device file: %v", err)
+			return fmt.Errorf("unable to create tuntap device file: %w", err)
 		}
 		if cfg.ProxyTargetIP != "" || cfg.ProxyTargetDNSName != "" || cfg.Routes != nil || cfg.TailnetTargetIP != "" || cfg.TailnetTargetFQDN != "" {
 			if err := ensureIPForwarding(cfg.Root, cfg.ProxyTargetIP, cfg.TailnetTargetIP, cfg.TailnetTargetFQDN, cfg.Routes); err != nil {
 				log.Printf("Failed to enable IP forwarding: %v", err)
 				log.Printf("To run tailscale as a proxy or router container, IP forwarding must be enabled.")
 				if cfg.InKubernetes {
-					log.Fatalf("You can either set the sysctls as a privileged initContainer, or run the tailscale container with privileged=true.")
+					return fmt.Errorf("you can either set the sysctls as a privileged initContainer, or run the tailscale container with privileged=true.")
 				} else {
-					log.Fatalf("You can fix this by running the container with privileged=true, or the equivalent in your container runtime that permits access to sysctls.")
+					return fmt.Errorf("you can fix this by running the container with privileged=true, or the equivalent in your container runtime that permits access to sysctls.")
 				}
 			}
 		}
 	}
 
-	// Context is used for all setup stuff until we're in steady
+	// Root context for the whole containerboot process, used to make sure
+	// shutdown signals are promptly and cleanly handled.
+	ctx, cancel := contextWithExitSignalWatch()
+	defer cancel()
+
+	// bootCtx is used for all setup stuff until we're in steady
 	// state, so that if something is hanging we eventually time out
 	// and crashloop the container.
-	bootCtx, cancel := context.WithTimeout(context.Background(), 60*time.Second)
+	bootCtx, cancel := context.WithTimeout(ctx, 60*time.Second)
 	defer cancel()
 
 	var kc *kubeClient
 	if cfg.InKubernetes {
 		kc, err = newKubeClient(cfg.Root, cfg.KubeSecret)
 		if err != nil {
-			log.Fatalf("error initializing kube client: %v", err)
+			return fmt.Errorf("error initializing kube client: %w", err)
 		}
 		if err := cfg.setupKube(bootCtx, kc); err != nil {
-			log.Fatalf("error setting up for running on Kubernetes: %v", err)
+			return fmt.Errorf("error setting up for running on Kubernetes: %w", err)
 		}
 	}
 
 	client, daemonProcess, err := startTailscaled(bootCtx, cfg)
 	if err != nil {
-		log.Fatalf("failed to bring up tailscale: %v", err)
+		return fmt.Errorf("failed to bring up tailscale: %w", err)
 	}
 	killTailscaled := func() {
+		if hasKubeStateStore(cfg) {
+			// Check we're not shutting tailscaled down while it's still writing
+			// state. If we authenticate and fail to write all the state, we'll
+			// never recover automatically.
+			//
+			// The default termination grace period for a Pod is 30s. We wait 25s at
+			// most so that we still reserve some of that budget for tailscaled
+			// to receive and react to a SIGTERM before the SIGKILL that k8s
+			// will send at the end of the grace period.
+			ctx, cancel := context.WithTimeout(context.Background(), 25*time.Second)
+			defer cancel()
+
+			log.Printf("Checking for consistent state")
+			err := kc.waitForConsistentState(ctx)
+			if err != nil {
+				log.Printf("Error waiting for consistent state on shutdown: %v", err)
+			}
+		}
+		log.Printf("Sending SIGTERM to tailscaled")
 		if err := daemonProcess.Signal(unix.SIGTERM); err != nil {
 			log.Fatalf("error shutting tailscaled down: %v", err)
 		}
@@ -191,17 +221,18 @@ func main() {
 	defer killTailscaled()
 
 	var healthCheck *healthz
+	ep := &egressProxy{}
 	if cfg.HealthCheckAddrPort != "" {
 		mux := http.NewServeMux()
 
 		log.Printf("Running healthcheck endpoint at %s/healthz", cfg.HealthCheckAddrPort)
-		healthCheck = healthHandlers(mux)
+		healthCheck = healthHandlers(mux, cfg.PodIPv4)
 
 		close := runHTTPServer(mux, cfg.HealthCheckAddrPort)
 		defer close()
 	}
 
-	if cfg.localMetricsEnabled() || cfg.localHealthEnabled() {
+	if cfg.localMetricsEnabled() || cfg.localHealthEnabled() || cfg.egressSvcsTerminateEPEnabled() {
 		mux := http.NewServeMux()
 
 		if cfg.localMetricsEnabled() {
@@ -211,7 +242,11 @@ func main() {
 
 		if cfg.localHealthEnabled() {
 			log.Printf("Running healthcheck endpoint at %s/healthz", cfg.LocalAddrPort)
-			healthCheck = healthHandlers(mux)
+			healthCheck = healthHandlers(mux, cfg.PodIPv4)
+		}
+		if cfg.EgressProxiesCfgPath != "" {
+			log.Printf("Running preshutdown hook at %s%s", cfg.LocalAddrPort, kubetypes.EgessServicesPreshutdownEP)
+			ep.registerHandlers(mux)
 		}
 
 		close := runHTTPServer(mux, cfg.LocalAddrPort)
@@ -226,7 +261,7 @@ func main() {
 
 	w, err := client.WatchIPNBus(bootCtx, ipn.NotifyInitialNetMap|ipn.NotifyInitialPrefs|ipn.NotifyInitialState)
 	if err != nil {
-		log.Fatalf("failed to watch tailscaled for updates: %v", err)
+		return fmt.Errorf("failed to watch tailscaled for updates: %w", err)
 	}
 
 	// Now that we've started tailscaled, we can symlink the socket to the
@@ -262,18 +297,18 @@ func main() {
 		didLogin = true
 		w.Close()
 		if err := tailscaleUp(bootCtx, cfg); err != nil {
-			return fmt.Errorf("failed to auth tailscale: %v", err)
+			return fmt.Errorf("failed to auth tailscale: %w", err)
 		}
 		w, err = client.WatchIPNBus(bootCtx, ipn.NotifyInitialNetMap|ipn.NotifyInitialState)
 		if err != nil {
-			return fmt.Errorf("rewatching tailscaled for updates after auth: %v", err)
+			return fmt.Errorf("rewatching tailscaled for updates after auth: %w", err)
 		}
 		return nil
 	}
 
 	if isTwoStepConfigAlwaysAuth(cfg) {
 		if err := authTailscale(); err != nil {
-			log.Fatalf("failed to auth tailscale: %v", err)
+			return fmt.Errorf("failed to auth tailscale: %w", err)
 		}
 	}
 
@@ -281,7 +316,7 @@ authLoop:
 	for {
 		n, err := w.Next()
 		if err != nil {
-			log.Fatalf("failed to read from tailscaled: %v", err)
+			return fmt.Errorf("failed to read from tailscaled: %w", err)
 		}
 
 		if n.State != nil {
@@ -290,10 +325,10 @@ authLoop:
 				if isOneStepConfig(cfg) {
 					// This could happen if this is the first time tailscaled was run for this
 					// device and the auth key was not passed via the configfile.
-					log.Fatalf("invalid state: tailscaled daemon started with a config file, but tailscale is not logged in: ensure you pass a valid auth key in the config file.")
+					return fmt.Errorf("invalid state: tailscaled daemon started with a config file, but tailscale is not logged in: ensure you pass a valid auth key in the config file.")
 				}
 				if err := authTailscale(); err != nil {
-					log.Fatalf("failed to auth tailscale: %v", err)
+					return fmt.Errorf("failed to auth tailscale: %w", err)
 				}
 			case ipn.NeedsMachineAuth:
 				log.Printf("machine authorization required, please visit the admin panel")
@@ -313,14 +348,11 @@ authLoop:
 
 	w.Close()
 
-	ctx, cancel := contextWithExitSignalWatch()
-	defer cancel()
-
 	if isTwoStepConfigAuthOnce(cfg) {
 		// Now that we are authenticated, we can set/reset any of the
 		// settings that we need to.
 		if err := tailscaleSet(ctx, cfg); err != nil {
-			log.Fatalf("failed to auth tailscale: %v", err)
+			return fmt.Errorf("failed to auth tailscale: %w", err)
 		}
 	}
 
@@ -329,11 +361,11 @@ authLoop:
 	if cfg.ServeConfigPath != "" {
 		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)
+			return fmt.Errorf("failed to unset serve config: %w", err)
 		}
 		if hasKubeStateStore(cfg) {
 			if err := kc.storeHTTPSEndpoint(ctx, ""); err != nil {
-				log.Fatalf("failed to update HTTPS endpoint in tailscale state: %v", err)
+				return fmt.Errorf("failed to update HTTPS endpoint in tailscale state: %w", err)
 			}
 		}
 	}
@@ -344,19 +376,25 @@ authLoop:
 		// wipe it, but it's good hygiene.
 		log.Printf("Deleting authkey from kube secret")
 		if err := kc.deleteAuthKey(ctx); err != nil {
-			log.Fatalf("deleting authkey from kube secret: %v", err)
+			return fmt.Errorf("deleting authkey from kube secret: %w", err)
 		}
 	}
 
 	if hasKubeStateStore(cfg) {
 		if err := kc.storeCapVerUID(ctx, cfg.PodUID); err != nil {
-			log.Fatalf("storing capability version and UID: %v", err)
+			return fmt.Errorf("storing capability version and UID: %w", err)
 		}
 	}
 
 	w, err = client.WatchIPNBus(ctx, ipn.NotifyInitialNetMap|ipn.NotifyInitialState)
 	if err != nil {
-		log.Fatalf("rewatching tailscaled for updates after auth: %v", err)
+		return fmt.Errorf("rewatching tailscaled for updates after auth: %w", 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 (
@@ -380,7 +418,7 @@ authLoop:
 	if isL3Proxy(cfg) {
 		nfr, err = newNetfilterRunner(log.Printf)
 		if err != nil {
-			log.Fatalf("error creating new netfilter runner: %v", err)
+			return fmt.Errorf("error creating new netfilter runner: %w", err)
 		}
 	}
 
@@ -451,7 +489,9 @@ runLoop:
 			killTailscaled()
 			break runLoop
 		case err := <-errChan:
-			log.Fatalf("failed to read from tailscaled: %v", err)
+			return fmt.Errorf("failed to read from tailscaled: %w", err)
+		case err := <-cfgWatchErrChan:
+			return fmt.Errorf("failed to watch tailscaled config: %w", err)
 		case n := <-notifyChan:
 			if n.State != nil && *n.State != ipn.Running {
 				// Something's gone wrong and we've left the authenticated state.
@@ -459,7 +499,7 @@ runLoop:
 				// control flow required to make it work now is hard. So, just crash
 				// the container and rely on the container runtime to restart us,
 				// whereupon we'll go through initial auth again.
-				log.Fatalf("tailscaled left running state (now in state %q), exiting", *n.State)
+				return fmt.Errorf("tailscaled left running state (now in state %q), exiting", *n.State)
 			}
 			if n.NetMap != nil {
 				addrs = n.NetMap.SelfNode.Addresses().AsSlice()
@@ -477,7 +517,7 @@ runLoop:
 				deviceID := n.NetMap.SelfNode.StableID()
 				if hasKubeStateStore(cfg) && deephash.Update(&currentDeviceID, &deviceID) {
 					if err := kc.storeDeviceID(ctx, n.NetMap.SelfNode.StableID()); err != nil {
-						log.Fatalf("storing device ID in Kubernetes Secret: %v", err)
+						return fmt.Errorf("storing device ID in Kubernetes Secret: %w", err)
 					}
 				}
 				if cfg.TailnetTargetFQDN != "" {
@@ -514,12 +554,12 @@ runLoop:
 								rulesInstalled = true
 								log.Printf("Installing forwarding rules for destination %v", ea.String())
 								if err := installEgressForwardingRule(ctx, ea.String(), addrs, nfr); err != nil {
-									log.Fatalf("installing egress proxy rules for destination %s: %v", ea.String(), err)
+									return fmt.Errorf("installing egress proxy rules for destination %s: %v", ea.String(), err)
 								}
 							}
 						}
 						if !rulesInstalled {
-							log.Fatalf("no forwarding rules for egress addresses %v, host supports IPv6: %v", egressAddrs, nfr.HasIPV6NAT())
+							return fmt.Errorf("no forwarding rules for egress addresses %v, host supports IPv6: %v", egressAddrs, nfr.HasIPV6NAT())
 						}
 					}
 					currentEgressIPs = newCurentEgressIPs
@@ -527,7 +567,7 @@ runLoop:
 				if cfg.ProxyTargetIP != "" && len(addrs) != 0 && ipsHaveChanged {
 					log.Printf("Installing proxy rules")
 					if err := installIngressForwardingRule(ctx, cfg.ProxyTargetIP, addrs, nfr); err != nil {
-						log.Fatalf("installing ingress proxy rules: %v", err)
+						return fmt.Errorf("installing ingress proxy rules: %w", err)
 					}
 				}
 				if cfg.ProxyTargetDNSName != "" && len(addrs) != 0 && ipsHaveChanged {
@@ -543,7 +583,7 @@ runLoop:
 					if backendsHaveChanged {
 						log.Printf("installing ingress proxy rules for backends %v", newBackendAddrs)
 						if err := installIngressForwardingRuleForDNSTarget(ctx, newBackendAddrs, addrs, nfr); err != nil {
-							log.Fatalf("error installing ingress proxy rules: %v", err)
+							return fmt.Errorf("error installing ingress proxy rules: %w", err)
 						}
 					}
 					resetTimer(false)
@@ -565,7 +605,7 @@ runLoop:
 				if cfg.TailnetTargetIP != "" && ipsHaveChanged && len(addrs) != 0 {
 					log.Printf("Installing forwarding rules for destination %v", cfg.TailnetTargetIP)
 					if err := installEgressForwardingRule(ctx, cfg.TailnetTargetIP, addrs, nfr); err != nil {
-						log.Fatalf("installing egress proxy rules: %v", err)
+						return fmt.Errorf("installing egress proxy rules: %w", err)
 					}
 				}
 				// If this is a L7 cluster ingress proxy (set up
@@ -577,7 +617,7 @@ runLoop:
 				if cfg.AllowProxyingClusterTrafficViaIngress && cfg.ServeConfigPath != "" && ipsHaveChanged && len(addrs) != 0 {
 					log.Printf("installing rules to forward traffic for %s to node's tailnet IP", cfg.PodIP)
 					if err := installTSForwardingRuleForDestination(ctx, cfg.PodIP, addrs, nfr); err != nil {
-						log.Fatalf("installing rules to forward traffic to node's tailnet IP: %v", err)
+						return fmt.Errorf("installing rules to forward traffic to node's tailnet IP: %w", err)
 					}
 				}
 				currentIPs = newCurrentIPs
@@ -596,7 +636,7 @@ runLoop:
 				deviceEndpoints := []any{n.NetMap.SelfNode.Name(), n.NetMap.SelfNode.Addresses()}
 				if hasKubeStateStore(cfg) && deephash.Update(&currentDeviceEndpoints, &deviceEndpoints) {
 					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)
+						return fmt.Errorf("storing device IPs and FQDN in Kubernetes Secret: %w", err)
 					}
 				}
 
@@ -631,20 +671,21 @@ runLoop:
 					// will then continuously monitor the config file and netmap updates and
 					// reconfigure the firewall rules as needed. If any of its operations fail, it
 					// will crash this node.
-					if cfg.EgressSvcsCfgPath != "" {
-						log.Printf("configuring egress proxy using configuration file at %s", cfg.EgressSvcsCfgPath)
+					if cfg.EgressProxiesCfgPath != "" {
+						log.Printf("configuring egress proxy using configuration file at %s", cfg.EgressProxiesCfgPath)
 						egressSvcsNotify = make(chan ipn.Notify)
-						ep := egressProxy{
-							cfgPath:      cfg.EgressSvcsCfgPath,
+						opts := egressProxyRunOpts{
+							cfgPath:      cfg.EgressProxiesCfgPath,
 							nfr:          nfr,
 							kc:           kc,
+							tsClient:     client,
 							stateSecret:  cfg.KubeSecret,
 							netmapChan:   egressSvcsNotify,
 							podIPv4:      cfg.PodIPv4,
 							tailnetAddrs: addrs,
 						}
 						go func() {
-							if err := ep.run(ctx, n); err != nil {
+							if err := ep.run(ctx, n, opts); err != nil {
 								egressSvcsErrorChan <- err
 							}
 						}()
@@ -686,16 +727,18 @@ runLoop:
 			if backendsHaveChanged && len(addrs) != 0 {
 				log.Printf("Backend address change detected, installing proxy rules for backends %v", newBackendAddrs)
 				if err := installIngressForwardingRuleForDNSTarget(ctx, newBackendAddrs, addrs, nfr); err != nil {
-					log.Fatalf("installing ingress proxy rules for DNS target %s: %v", cfg.ProxyTargetDNSName, err)
+					return fmt.Errorf("installing ingress proxy rules for DNS target %s: %v", cfg.ProxyTargetDNSName, err)
 				}
 			}
 			backendAddrs = newBackendAddrs
 			resetTimer(false)
 		case e := <-egressSvcsErrorChan:
-			log.Fatalf("egress proxy failed: %v", e)
+			return fmt.Errorf("egress proxy failed: %v", e)
 		}
 	}
 	wg.Wait()
+
+	return nil
 }
 
 // ensureTunFile checks that /dev/net/tun exists, creating it if
@@ -724,13 +767,13 @@ func resolveDNS(ctx context.Context, name string) ([]net.IP, error) {
 	ip4s, err := net.DefaultResolver.LookupIP(ctx, "ip4", name)
 	if err != nil {
 		if e, ok := err.(*net.DNSError); !(ok && e.IsNotFound) {
-			return nil, fmt.Errorf("error looking up IPv4 addresses: %v", err)
+			return nil, fmt.Errorf("error looking up IPv4 addresses: %w", err)
 		}
 	}
 	ip6s, err := net.DefaultResolver.LookupIP(ctx, "ip6", name)
 	if err != nil {
 		if e, ok := err.(*net.DNSError); !(ok && e.IsNotFound) {
-			return nil, fmt.Errorf("error looking up IPv6 addresses: %v", err)
+			return nil, fmt.Errorf("error looking up IPv6 addresses: %w", err)
 		}
 	}
 	if len(ip4s) == 0 && len(ip6s) == 0 {
@@ -743,7 +786,7 @@ func resolveDNS(ctx context.Context, name string) ([]net.IP, error) {
 // context that gets cancelled when a signal is received and a cancel function
 // that can be called to free the resources when the watch should be stopped.
 func contextWithExitSignalWatch() (context.Context, func()) {
-	closeChan := make(chan string)
+	closeChan := make(chan struct{})
 	ctx, cancel := context.WithCancel(context.Background())
 	signalChan := make(chan os.Signal, 1)
 	signal.Notify(signalChan, syscall.SIGINT, syscall.SIGTERM)
@@ -755,8 +798,11 @@ func contextWithExitSignalWatch() (context.Context, func()) {
 			return
 		}
 	}()
+	closeOnce := sync.Once{}
 	f := func() {
-		closeChan <- "goodbye"
+		closeOnce.Do(func() {
+			close(closeChan)
+		})
 	}
 	return ctx, f
 }
@@ -809,7 +855,11 @@ func runHTTPServer(mux *http.ServeMux, addr string) (close func() error) {
 
 	go func() {
 		if err := srv.Serve(ln); err != nil {
-			log.Fatalf("failed running server: %v", err)
+			if err != http.ErrServerClosed {
+				log.Fatalf("failed running server: %v", err)
+			} else {
+				log.Printf("HTTP server at %s closed", addr)
+			}
 		}
 	}()
 

cmd/containerboot/main_test.go

@@ -25,6 +25,7 @@ import (
 	"strconv"
 	"strings"
 	"sync"
+	"syscall"
 	"testing"
 	"time"
 
@@ -32,6 +33,8 @@ import (
 	"golang.org/x/sys/unix"
 	"tailscale.com/ipn"
 	"tailscale.com/kube/egressservices"
+	"tailscale.com/kube/kubeclient"
+	"tailscale.com/kube/kubetypes"
 	"tailscale.com/tailcfg"
 	"tailscale.com/tstest"
 	"tailscale.com/types/netmap"
@@ -48,26 +51,13 @@ func TestContainerBoot(t *testing.T) {
 	defer lapi.Close()
 
 	kube := kubeServer{FSRoot: d}
-	if err := kube.Start(); err != nil {
-		t.Fatal(err)
-	}
+	kube.Start(t)
 	defer kube.Close()
 
 	tailscaledConf := &ipn.ConfigVAlpha{AuthKey: ptr.To("foo"), Version: "alpha0"}
-	tailscaledConfBytes, err := json.Marshal(tailscaledConf)
-	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)
-	}
+	egressCfg := egressSvcConfig("foo", "foo.tailnetxyz.ts.net")
+	egressStatus := egressSvcStatus("foo", "foo.tailnetxyz.ts.net")
 
 	dirs := []string{
 		"var/lib",
@@ -84,16 +74,17 @@ 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,
-		"etc/tailscaled/serve-config.json":           serveConfBytes,
-		"etc/tailscaled/egress-services-config.json": egressSvcsCfgBytes,
+		"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":          mustJSON(t, tailscaledConf),
+		"etc/tailscaled/serve-config.json":      mustJSON(t, serveConf),
+		filepath.Join("etc/tailscaled/", egressservices.KeyEgressServices): mustJSON(t, egressCfg),
+		filepath.Join("etc/tailscaled/", egressservices.KeyHEPPings):       []byte("4"),
 	}
 	resetFiles := func() {
 		for path, content := range files {
@@ -132,6 +123,9 @@ func TestContainerBoot(t *testing.T) {
 	healthURL := func(port int) string {
 		return fmt.Sprintf("http://127.0.0.1:%d/healthz", port)
 	}
+	egressSvcTerminateURL := func(port int) string {
+		return fmt.Sprintf("http://127.0.0.1:%d%s", port, kubetypes.EgessServicesPreshutdownEP)
+	}
 
 	capver := fmt.Sprintf("%d", tailcfg.CurrentCapabilityVersion)
 
@@ -143,15 +137,29 @@ func TestContainerBoot(t *testing.T) {
 
 		// WantCmds is the commands that containerboot should run in this phase.
 		WantCmds []string
+
 		// WantKubeSecret is the secret keys/values that should exist in the
 		// kube secret.
 		WantKubeSecret map[string]string
+
+		// Update the kube secret with these keys/values at the beginning of the
+		// phase (simulates our fake tailscaled doing it).
+		UpdateKubeSecret map[string]string
+
 		// WantFiles files that should exist in the container and their
 		// contents.
 		WantFiles map[string]string
-		// WantFatalLog is the fatal log message we expect from containerboot.
-		// If set for a phase, the test will finish on that phase.
-		WantFatalLog string
+
+		// WantLog is a log message we expect from containerboot.
+		WantLog string
+
+		// If set for a phase, the test will expect containerboot to exit with
+		// this error code, and the test will finish on that phase without
+		// waiting for the successful startup log message.
+		WantExitCode *int
+
+		// The signal to send to containerboot at the start of the phase.
+		Signal *syscall.Signal
 
 		EndpointStatuses map[string]int
 	}
@@ -439,7 +447,8 @@ func TestContainerBoot(t *testing.T) {
 							},
 						},
 					},
-					WantFatalLog: "no forwarding rules for egress addresses [::1/128], host supports IPv6: false",
+					WantLog:      "no forwarding rules for egress addresses [::1/128], host supports IPv6: false",
+					WantExitCode: ptr.To(1),
 				},
 			},
 		},
@@ -896,9 +905,10 @@ func TestContainerBoot(t *testing.T) {
 		{
 			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"),
+				"KUBERNETES_SERVICE_HOST":       kube.Host,
+				"KUBERNETES_SERVICE_PORT_HTTPS": kube.Port,
+				"TS_EGRESS_PROXIES_CONFIG_PATH": filepath.Join(d, "etc/tailscaled"),
+				"TS_LOCAL_ADDR_PORT":            fmt.Sprintf("[::]:%d", localAddrPort),
 			},
 			KubeSecret: map[string]string{
 				"authkey": "tskey-key",
@@ -912,28 +922,92 @@ func TestContainerBoot(t *testing.T) {
 					WantKubeSecret: map[string]string{
 						"authkey": "tskey-key",
 					},
+					EndpointStatuses: map[string]int{
+						egressSvcTerminateURL(localAddrPort): 200,
+					},
 				},
 				{
 					Notify: runningNotify,
 					WantKubeSecret: map[string]string{
+						"egress-services":  mustBase64(t, egressStatus),
 						"authkey":          "tskey-key",
 						"device_fqdn":      "test-node.test.ts.net",
 						"device_id":        "myID",
 						"device_ips":       `["100.64.0.1"]`,
 						"tailscale_capver": capver,
 					},
+					EndpointStatuses: map[string]int{
+						egressSvcTerminateURL(localAddrPort): 200,
+					},
 				},
 			},
 		},
 		{
 			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",
+				"TS_EGRESS_PROXIES_CONFIG_PATH": filepath.Join(d, "etc/tailscaled"),
+				"TS_AUTHKEY":                    "tskey-key",
 			},
 			Phases: []phase{
 				{
-					WantFatalLog: "TS_EGRESS_SERVICES_CONFIG_PATH is only supported for Tailscale running on Kubernetes",
+					WantLog:      "TS_EGRESS_PROXIES_CONFIG_PATH is only supported for Tailscale running on Kubernetes",
+					WantExitCode: ptr.To(1),
+				},
+			},
+		},
+		{
+			Name: "kube_shutdown_during_state_write",
+			Env: map[string]string{
+				"KUBERNETES_SERVICE_HOST":       kube.Host,
+				"KUBERNETES_SERVICE_PORT_HTTPS": kube.Port,
+				"TS_ENABLE_HEALTH_CHECK":        "true",
+			},
+			KubeSecret: map[string]string{
+				"authkey": "tskey-key",
+			},
+			Phases: []phase{
+				{
+					// Normal startup.
+					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",
+					},
+				},
+				{
+					// SIGTERM before state is finished writing, should wait for
+					// consistent state before propagating SIGTERM to tailscaled.
+					Signal: ptr.To(unix.SIGTERM),
+					UpdateKubeSecret: map[string]string{
+						"_machinekey":  "foo",
+						"_profiles":    "foo",
+						"profile-baff": "foo",
+						// Missing "_current-profile" key.
+					},
+					WantKubeSecret: map[string]string{
+						"authkey":      "tskey-key",
+						"_machinekey":  "foo",
+						"_profiles":    "foo",
+						"profile-baff": "foo",
+					},
+					WantLog: "Waiting for tailscaled to finish writing state to Secret \"tailscale\"",
+				},
+				{
+					// tailscaled has finished writing state, should propagate SIGTERM.
+					UpdateKubeSecret: map[string]string{
+						"_current-profile": "foo",
+					},
+					WantKubeSecret: map[string]string{
+						"authkey":          "tskey-key",
+						"_machinekey":      "foo",
+						"_profiles":        "foo",
+						"profile-baff":     "foo",
+						"_current-profile": "foo",
+					},
+					WantLog:      "HTTP server at [::]:9002 closed",
+					WantExitCode: ptr.To(0),
 				},
 			},
 		},
@@ -981,26 +1055,36 @@ func TestContainerBoot(t *testing.T) {
 
 			var wantCmds []string
 			for i, p := range test.Phases {
+				for k, v := range p.UpdateKubeSecret {
+					kube.SetSecret(k, v)
+				}
 				lapi.Notify(p.Notify)
-				if p.WantFatalLog != "" {
+				if p.Signal != nil {
+					cmd.Process.Signal(*p.Signal)
+				}
+				if p.WantLog != "" {
 					err := tstest.WaitFor(2*time.Second, func() error {
-						state, err := cmd.Process.Wait()
-						if err != nil {
-							return err
-						}
-						if state.ExitCode() != 1 {
-							return fmt.Errorf("process exited with code %d but wanted %d", state.ExitCode(), 1)
-						}
-						waitLogLine(t, time.Second, cbOut, p.WantFatalLog)
+						waitLogLine(t, time.Second, cbOut, p.WantLog)
 						return nil
 					})
 					if err != nil {
 						t.Fatal(err)
 					}
+				}
+
+				if p.WantExitCode != nil {
+					state, err := cmd.Process.Wait()
+					if err != nil {
+						t.Fatal(err)
+					}
+					if state.ExitCode() != *p.WantExitCode {
+						t.Fatalf("phase %d: want exit code %d, got %d", i, *p.WantExitCode, state.ExitCode())
+					}
 
 					// Early test return, we don't expect the successful startup log message.
 					return
 				}
+
 				wantCmds = append(wantCmds, p.WantCmds...)
 				waitArgs(t, 2*time.Second, d, argFile, strings.Join(wantCmds, "\n"))
 				err := tstest.WaitFor(2*time.Second, func() error {
@@ -1056,6 +1140,9 @@ func TestContainerBoot(t *testing.T) {
 				}
 			}
 			waitLogLine(t, 2*time.Second, cbOut, "Startup complete, waiting for shutdown signal")
+			if cmd.ProcessState != nil {
+				t.Fatalf("containerboot should be running but exited with exit code %d", cmd.ProcessState.ExitCode())
+			}
 		})
 	}
 }
@@ -1287,18 +1374,18 @@ func (k *kubeServer) Reset() {
 	k.secret = map[string]string{}
 }
 
-func (k *kubeServer) Start() error {
+func (k *kubeServer) Start(t *testing.T) {
 	root := filepath.Join(k.FSRoot, "var/run/secrets/kubernetes.io/serviceaccount")
 
 	if err := os.MkdirAll(root, 0700); err != nil {
-		return err
+		t.Fatal(err)
 	}
 
 	if err := os.WriteFile(filepath.Join(root, "namespace"), []byte("default"), 0600); err != nil {
-		return err
+		t.Fatal(err)
 	}
 	if err := os.WriteFile(filepath.Join(root, "token"), []byte("bearer_token"), 0600); err != nil {
-		return err
+		t.Fatal(err)
 	}
 
 	k.srv = httptest.NewTLSServer(k)
@@ -1307,13 +1394,11 @@ func (k *kubeServer) Start() error {
 
 	var cert bytes.Buffer
 	if err := pem.Encode(&cert, &pem.Block{Type: "CERTIFICATE", Bytes: k.srv.Certificate().Raw}); err != nil {
-		return err
+		t.Fatal(err)
 	}
 	if err := os.WriteFile(filepath.Join(root, "ca.crt"), cert.Bytes(), 0600); err != nil {
-		return err
+		t.Fatal(err)
 	}
-
-	return nil
 }
 
 func (k *kubeServer) Close() {
@@ -1362,6 +1447,7 @@ func (k *kubeServer) serveSecret(w http.ResponseWriter, r *http.Request) {
 		http.Error(w, fmt.Sprintf("reading request body: %v", err), http.StatusInternalServerError)
 		return
 	}
+	defer r.Body.Close()
 
 	switch r.Method {
 	case "GET":
@@ -1394,13 +1480,32 @@ func (k *kubeServer) serveSecret(w http.ResponseWriter, r *http.Request) {
 				panic(fmt.Sprintf("json decode failed: %v. Body:\n\n%s", err, string(bs)))
 			}
 			for _, op := range req {
-				if op.Op != "remove" {
+				switch op.Op {
+				case "remove":
+					if !strings.HasPrefix(op.Path, "/data/") {
+						panic(fmt.Sprintf("unsupported json-patch path %q", op.Path))
+					}
+					delete(k.secret, strings.TrimPrefix(op.Path, "/data/"))
+				case "replace":
+					path, ok := strings.CutPrefix(op.Path, "/data/")
+					if !ok {
+						panic(fmt.Sprintf("unsupported json-patch path %q", op.Path))
+					}
+					req := make([]kubeclient.JSONPatch, 0)
+					if err := json.Unmarshal(bs, &req); err != nil {
+						panic(fmt.Sprintf("json decode failed: %v. Body:\n\n%s", err, string(bs)))
+					}
+
+					for _, patch := range req {
+						val, ok := patch.Value.(string)
+						if !ok {
+							panic(fmt.Sprintf("unsupported json patch value %v: cannot be converted to string", patch.Value))
+						}
+						k.secret[path] = val
+					}
+				default:
 					panic(fmt.Sprintf("unsupported json-patch op %q", op.Op))
 				}
-				if !strings.HasPrefix(op.Path, "/data/") {
-					panic(fmt.Sprintf("unsupported json-patch path %q", op.Path))
-				}
-				delete(k.secret, strings.TrimPrefix(op.Path, "/data/"))
 			}
 		case "application/strategic-merge-patch+json":
 			req := struct {
@@ -1416,6 +1521,44 @@ func (k *kubeServer) serveSecret(w http.ResponseWriter, r *http.Request) {
 			panic(fmt.Sprintf("unknown content type %q", r.Header.Get("Content-Type")))
 		}
 	default:
-		panic(fmt.Sprintf("unhandled HTTP method %q", r.Method))
+		panic(fmt.Sprintf("unhandled HTTP request %s %s", r.Method, r.URL))
+	}
+}
+
+func mustBase64(t *testing.T, v any) string {
+	b := mustJSON(t, v)
+	s := base64.StdEncoding.WithPadding('=').EncodeToString(b)
+	return s
+}
+
+func mustJSON(t *testing.T, v any) []byte {
+	b, err := json.Marshal(v)
+	if err != nil {
+		t.Fatalf("error converting %v to json: %v", v, err)
+	}
+	return b
+}
+
+// egress services status given one named tailnet target specified by FQDN. As written by the proxy to its state Secret.
+func egressSvcStatus(name, fqdn string) egressservices.Status {
+	return egressservices.Status{
+		Services: map[string]*egressservices.ServiceStatus{
+			name: {
+				TailnetTarget: egressservices.TailnetTarget{
+					FQDN: fqdn,
+				},
+			},
+		},
+	}
+}
+
+// egress config given one named tailnet target specified by FQDN.
+func egressSvcConfig(name, fqdn string) egressservices.Configs {
+	return egressservices.Configs{
+		name: egressservices.Config{
+			TailnetTarget: egressservices.TailnetTarget{
+				FQDN: fqdn,
+			},
+		},
 	}
 }

cmd/containerboot/serve.go

@@ -65,10 +65,13 @@ func watchServeConfigChanges(ctx context.Context, path string, cdChanged <-chan
 		if err != nil {
 			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
 		}
-		validateHTTPSServe(certDomain, sc)
 		if err := updateServeConfig(ctx, sc, certDomain, lc); err != nil {
 			log.Fatalf("serve proxy: error updating serve config: %v", err)
 		}
@@ -88,27 +91,34 @@ func certDomainFromNetmap(nm *netmap.NetworkMap) string {
 	return nm.DNS.CertDomains[0]
 }
 
-func updateServeConfig(ctx context.Context, sc *ipn.ServeConfig, certDomain string, lc *tailscale.LocalClient) error {
-	// TODO(irbekrm): This means that serve config that does not expose HTTPS endpoint will not be set for a tailnet
-	// that does not have HTTPS enabled. We probably want to fix this.
-	if certDomain == kubetypes.ValueNoHTTPS {
+// 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 validateHTTPSServe(certDomain string, sc *ipn.ServeConfig) {
-	if certDomain != kubetypes.ValueNoHTTPS || !hasHTTPSEndpoint(sc) {
-		return
-	}
-	log.Printf(
-		`serve proxy: this node is configured as a proxy that exposes an HTTPS endpoint to tailnet,
+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
@@ -125,8 +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

@@ -11,18 +11,24 @@ import (
 	"errors"
 	"fmt"
 	"log"
+	"net/http"
 	"net/netip"
 	"os"
 	"path/filepath"
 	"reflect"
+	"strconv"
 	"strings"
 	"time"
 
 	"github.com/fsnotify/fsnotify"
+	"tailscale.com/client/tailscale"
 	"tailscale.com/ipn"
 	"tailscale.com/kube/egressservices"
 	"tailscale.com/kube/kubeclient"
+	"tailscale.com/kube/kubetypes"
+	"tailscale.com/syncs"
 	"tailscale.com/tailcfg"
+	"tailscale.com/util/httpm"
 	"tailscale.com/util/linuxfw"
 	"tailscale.com/util/mak"
 )
@@ -37,13 +43,15 @@ const tailscaleTunInterface = "tailscale0"
 // egressProxy knows how to configure firewall rules to route cluster traffic to
 // one or more tailnet services.
 type egressProxy struct {
-	cfgPath string // path to egress service config file
+	cfgPath string // path to a directory with egress services config files
 
 	nfr linuxfw.NetfilterRunner // never nil
 
 	kc          kubeclient.Client // never nil
 	stateSecret string            // name of the kube state Secret
 
+	tsClient *tailscale.LocalClient // never nil
+
 	netmapChan chan ipn.Notify // chan to receive netmap updates on
 
 	podIPv4 string // never empty string, currently only IPv4 is supported
@@ -55,15 +63,29 @@ type egressProxy struct {
 	// memory at all.
 	targetFQDNs map[string][]netip.Prefix
 
-	// used to configure firewall rules.
-	tailnetAddrs []netip.Prefix
+	tailnetAddrs []netip.Prefix // tailnet IPs of this tailnet device
+
+	// shortSleep is the backoff sleep between healthcheck endpoint calls - can be overridden in tests.
+	shortSleep time.Duration
+	// longSleep is the time to sleep after the routing rules are updated to increase the chance that kube
+	// proxies on all nodes have updated their routing configuration. It can be configured to 0 in
+	// tests.
+	longSleep time.Duration
+	// client is a client that can send HTTP requests.
+	client httpClient
+}
+
+// httpClient is a client that can send HTTP requests and can be mocked in tests.
+type httpClient interface {
+	Do(*http.Request) (*http.Response, error)
 }
 
 // run configures egress proxy firewall rules and ensures that the firewall rules are reconfigured when:
 // - the mounted egress config has changed
 // - the proxy's tailnet IP addresses have changed
 // - tailnet IPs have changed for any backend targets specified by tailnet FQDN
-func (ep *egressProxy) run(ctx context.Context, n ipn.Notify) error {
+func (ep *egressProxy) run(ctx context.Context, n ipn.Notify, opts egressProxyRunOpts) error {
+	ep.configure(opts)
 	var tickChan <-chan time.Time
 	var eventChan <-chan fsnotify.Event
 	// TODO (irbekrm): take a look if this can be pulled into a single func
@@ -75,7 +97,7 @@ func (ep *egressProxy) run(ctx context.Context, n ipn.Notify) error {
 		tickChan = ticker.C
 	} else {
 		defer w.Close()
-		if err := w.Add(filepath.Dir(ep.cfgPath)); err != nil {
+		if err := w.Add(ep.cfgPath); err != nil {
 			return fmt.Errorf("failed to add fsnotify watch: %w", err)
 		}
 		eventChan = w.Events
@@ -85,28 +107,52 @@ func (ep *egressProxy) run(ctx context.Context, n ipn.Notify) error {
 		return err
 	}
 	for {
-		var err error
 		select {
 		case <-ctx.Done():
 			return nil
 		case <-tickChan:
-			err = ep.sync(ctx, n)
+			log.Printf("periodic sync, ensuring firewall config is up to date...")
 		case <-eventChan:
 			log.Printf("config file change detected, ensuring firewall config is up to date...")
-			err = ep.sync(ctx, n)
 		case n = <-ep.netmapChan:
 			shouldResync := ep.shouldResync(n)
-			if shouldResync {
-				log.Printf("netmap change detected, ensuring firewall config is up to date...")
-				err = ep.sync(ctx, n)
+			if !shouldResync {
+				continue
 			}
+			log.Printf("netmap change detected, ensuring firewall config is up to date...")
 		}
-		if err != nil {
+		if err := ep.sync(ctx, n); err != nil {
 			return fmt.Errorf("error syncing egress service config: %w", err)
 		}
 	}
 }
 
+type egressProxyRunOpts struct {
+	cfgPath      string
+	nfr          linuxfw.NetfilterRunner
+	kc           kubeclient.Client
+	tsClient     *tailscale.LocalClient
+	stateSecret  string
+	netmapChan   chan ipn.Notify
+	podIPv4      string
+	tailnetAddrs []netip.Prefix
+}
+
+// applyOpts configures egress proxy using the provided options.
+func (ep *egressProxy) configure(opts egressProxyRunOpts) {
+	ep.cfgPath = opts.cfgPath
+	ep.nfr = opts.nfr
+	ep.kc = opts.kc
+	ep.tsClient = opts.tsClient
+	ep.stateSecret = opts.stateSecret
+	ep.netmapChan = opts.netmapChan
+	ep.podIPv4 = opts.podIPv4
+	ep.tailnetAddrs = opts.tailnetAddrs
+	ep.client = &http.Client{} // default HTTP client
+	ep.shortSleep = time.Second
+	ep.longSleep = time.Second * 10
+}
+
 // sync triggers an egress proxy config resync. The resync calculates the diff between config and status to determine if
 // any firewall rules need to be updated. Currently using status in state Secret as a reference for what is the current
 // firewall configuration is good enough because - the status is keyed by the Pod IP - we crash the Pod on errors such
@@ -327,7 +373,8 @@ func (ep *egressProxy) deleteUnnecessaryServices(cfgs *egressservices.Configs, s
 
 // getConfigs gets the mounted egress service configuration.
 func (ep *egressProxy) getConfigs() (*egressservices.Configs, error) {
-	j, err := os.ReadFile(ep.cfgPath)
+	svcsCfg := filepath.Join(ep.cfgPath, egressservices.KeyEgressServices)
+	j, err := os.ReadFile(svcsCfg)
 	if os.IsNotExist(err) {
 		return nil, nil
 	}
@@ -569,3 +616,142 @@ func servicesStatusIsEqual(st, st1 *egressservices.Status) bool {
 	st1.PodIPv4 = ""
 	return reflect.DeepEqual(*st, *st1)
 }
+
+// registerHandlers adds a new handler to the provided ServeMux that can be called as a Kubernetes prestop hook to
+// delay shutdown till it's safe to do so.
+func (ep *egressProxy) registerHandlers(mux *http.ServeMux) {
+	mux.Handle(fmt.Sprintf("GET %s", kubetypes.EgessServicesPreshutdownEP), ep)
+}
+
+// ServeHTTP serves /internal-egress-services-preshutdown endpoint, when it receives a request, it periodically polls
+// the configured health check endpoint for each egress service till it the health check endpoint no longer hits this
+// proxy Pod. It uses the Pod-IPv4 header to verify if health check response is received from this Pod.
+func (ep *egressProxy) ServeHTTP(w http.ResponseWriter, r *http.Request) {
+	cfgs, err := ep.getConfigs()
+	if err != nil {
+		http.Error(w, fmt.Sprintf("error retrieving egress services configs: %v", err), http.StatusInternalServerError)
+		return
+	}
+	if cfgs == nil {
+		if _, err := w.Write([]byte("safe to terminate")); err != nil {
+			http.Error(w, fmt.Sprintf("error writing termination status: %v", err), http.StatusInternalServerError)
+			return
+		}
+	}
+	hp, err := ep.getHEPPings()
+	if err != nil {
+		http.Error(w, fmt.Sprintf("error determining the number of times health check endpoint should be pinged: %v", err), http.StatusInternalServerError)
+		return
+	}
+	ep.waitTillSafeToShutdown(r.Context(), cfgs, hp)
+}
+
+// waitTillSafeToShutdown looks up all egress targets configured to be proxied via this instance and, for each target
+// whose configuration includes a healthcheck endpoint, pings the endpoint till none of the responses
+// are returned by this instance or till the HTTP request times out. In practice, the endpoint will be a Kubernetes Service for whom one of the backends
+// would normally be this Pod. When this Pod is being deleted, the operator should have removed it from the Service
+// backends and eventually kube proxy routing rules should be updated to no longer route traffic for the Service to this
+// Pod.
+func (ep *egressProxy) waitTillSafeToShutdown(ctx context.Context, cfgs *egressservices.Configs, hp int) {
+	if cfgs == nil || len(*cfgs) == 0 { // avoid sleeping if no services are configured
+		return
+	}
+	log.Printf("Ensuring that cluster traffic for egress targets is no longer routed via this Pod...")
+	wg := syncs.WaitGroup{}
+
+	for s, cfg := range *cfgs {
+		hep := cfg.HealthCheckEndpoint
+		if hep == "" {
+			log.Printf("Tailnet target %q does not have a cluster healthcheck specified, unable to verify if cluster traffic for the target is still routed via this Pod", s)
+			continue
+		}
+		svc := s
+		wg.Go(func() {
+			log.Printf("Ensuring that cluster traffic is no longer routed to %q via this Pod...", svc)
+			for {
+				if ctx.Err() != nil { // kubelet's HTTP request timeout
+					log.Printf("Cluster traffic for %s did not stop being routed to this Pod.", svc)
+					return
+				}
+				found, err := lookupPodRoute(ctx, hep, ep.podIPv4, hp, ep.client)
+				if err != nil {
+					log.Printf("unable to reach endpoint %q, assuming the routing rules for this Pod have been deleted: %v", hep, err)
+					break
+				}
+				if !found {
+					log.Printf("service %q is no longer routed through this Pod", svc)
+					break
+				}
+				log.Printf("service %q is still routed through this Pod, waiting...", svc)
+				time.Sleep(ep.shortSleep)
+			}
+		})
+	}
+	wg.Wait()
+	// The check above really only checked that the routing rules are updated on this node. Sleep for a bit to
+	// ensure that the routing rules are updated on other nodes. TODO(irbekrm): this may or may not be good enough.
+	// If it's not good enough, we'd probably want to do something more complex, where the proxies check each other.
+	log.Printf("Sleeping for %s before shutdown to ensure that kube proxies on all nodes have updated routing configuration", ep.longSleep)
+	time.Sleep(ep.longSleep)
+}
+
+// lookupPodRoute calls the healthcheck endpoint repeat times and returns true if the endpoint returns with the podIP
+// header at least once.
+func lookupPodRoute(ctx context.Context, hep, podIP string, repeat int, client httpClient) (bool, error) {
+	for range repeat {
+		f, err := lookup(ctx, hep, podIP, client)
+		if err != nil {
+			return false, err
+		}
+		if f {
+			return true, nil
+		}
+	}
+	return false, nil
+}
+
+// lookup calls the healthcheck endpoint and returns true if the response contains the podIP header.
+func lookup(ctx context.Context, hep, podIP string, client httpClient) (bool, error) {
+	req, err := http.NewRequestWithContext(ctx, httpm.GET, hep, nil)
+	if err != nil {
+		return false, fmt.Errorf("error creating new HTTP request: %v", err)
+	}
+
+	// Close the TCP connection to ensure that the next request is routed to a different backend.
+	req.Close = true
+
+	resp, err := client.Do(req)
+	if err != nil {
+		log.Printf("Endpoint %q can not be reached: %v, likely because there are no (more) healthy backends", hep, err)
+		return true, nil
+	}
+	defer resp.Body.Close()
+	gotIP := resp.Header.Get(kubetypes.PodIPv4Header)
+	return strings.EqualFold(podIP, gotIP), nil
+}
+
+// getHEPPings gets the number of pings that should be sent to a health check endpoint to ensure that each configured
+// backend is hit. This assumes that a health check endpoint is a Kubernetes Service and traffic to backend Pods is
+// round robin load balanced.
+func (ep *egressProxy) getHEPPings() (int, error) {
+	hepPingsPath := filepath.Join(ep.cfgPath, egressservices.KeyHEPPings)
+	j, err := os.ReadFile(hepPingsPath)
+	if os.IsNotExist(err) {
+		return 0, nil
+	}
+	if err != nil {
+		return -1, err
+	}
+	if len(j) == 0 || string(j) == "" {
+		return 0, nil
+	}
+	hp, err := strconv.Atoi(string(j))
+	if err != nil {
+		return -1, fmt.Errorf("error parsing hep pings as int: %v", err)
+	}
+	if hp < 0 {
+		log.Printf("[unexpected] hep pings is negative: %d", hp)
+		return 0, nil
+	}
+	return hp, nil
+}

cmd/containerboot/services_test.go

@@ -6,11 +6,18 @@
 package main
 
 import (
+	"context"
+	"fmt"
+	"io"
+	"net/http"
 	"net/netip"
 	"reflect"
+	"strings"
+	"sync"
 	"testing"
 
 	"tailscale.com/kube/egressservices"
+	"tailscale.com/kube/kubetypes"
 )
 
 func Test_updatesForSvc(t *testing.T) {
@@ -173,3 +180,145 @@ func Test_updatesForSvc(t *testing.T) {
 		})
 	}
 }
+
+// A failure of this test will most likely look like a timeout.
+func TestWaitTillSafeToShutdown(t *testing.T) {
+	podIP := "10.0.0.1"
+	anotherIP := "10.0.0.2"
+
+	tests := []struct {
+		name string
+		// services is a map of service name to the number of calls to make to the healthcheck endpoint before
+		// returning a response that does NOT contain this Pod's IP in headers.
+		services       map[string]int
+		replicas       int
+		healthCheckSet bool
+	}{
+		{
+			name: "no_configs",
+		},
+		{
+			name: "one_service_immediately_safe_to_shutdown",
+			services: map[string]int{
+				"svc1": 0,
+			},
+			replicas:       2,
+			healthCheckSet: true,
+		},
+		{
+			name: "multiple_services_immediately_safe_to_shutdown",
+			services: map[string]int{
+				"svc1": 0,
+				"svc2": 0,
+				"svc3": 0,
+			},
+			replicas:       2,
+			healthCheckSet: true,
+		},
+		{
+			name: "multiple_services_no_healthcheck_endpoints",
+			services: map[string]int{
+				"svc1": 0,
+				"svc2": 0,
+				"svc3": 0,
+			},
+			replicas: 2,
+		},
+		{
+			name: "one_service_eventually_safe_to_shutdown",
+			services: map[string]int{
+				"svc1": 3, // After 3 calls to health check endpoint, no longer returns this Pod's IP
+			},
+			replicas:       2,
+			healthCheckSet: true,
+		},
+		{
+			name: "multiple_services_eventually_safe_to_shutdown",
+			services: map[string]int{
+				"svc1": 1, // After 1 call to health check endpoint, no longer returns this Pod's IP
+				"svc2": 3, // After 3 calls to health check endpoint, no longer returns this Pod's IP
+				"svc3": 5, // After 5 calls to the health check endpoint, no longer returns this Pod's IP
+			},
+			replicas:       2,
+			healthCheckSet: true,
+		},
+		{
+			name: "multiple_services_eventually_safe_to_shutdown_with_higher_replica_count",
+			services: map[string]int{
+				"svc1": 7,
+				"svc2": 10,
+			},
+			replicas:       5,
+			healthCheckSet: true,
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			cfgs := &egressservices.Configs{}
+			switches := make(map[string]int)
+
+			for svc, callsToSwitch := range tt.services {
+				endpoint := fmt.Sprintf("http://%s.local", svc)
+				if tt.healthCheckSet {
+					(*cfgs)[svc] = egressservices.Config{
+						HealthCheckEndpoint: endpoint,
+					}
+				}
+				switches[endpoint] = callsToSwitch
+			}
+
+			ep := &egressProxy{
+				podIPv4: podIP,
+				client: &mockHTTPClient{
+					podIP:     podIP,
+					anotherIP: anotherIP,
+					switches:  switches,
+				},
+			}
+
+			ep.waitTillSafeToShutdown(context.Background(), cfgs, tt.replicas)
+		})
+	}
+}
+
+// mockHTTPClient is a client that receives an HTTP call for an egress service endpoint and returns a response with an
+// IP address in a 'Pod-IPv4' header. It can be configured to return one IP address for N calls, then switch to another
+// IP address to simulate a scenario where an IP is eventually no longer a backend for an endpoint.
+// TODO(irbekrm): to test this more thoroughly, we should have the client take into account the number of replicas and
+// return as if traffic was round robin load balanced across different Pods.
+type mockHTTPClient struct {
+	// podIP - initial IP address to return, that matches the current proxy's IP address.
+	podIP     string
+	anotherIP string
+	// after how many calls to an endpoint, the client should start returning 'anotherIP' instead of 'podIP.
+	switches map[string]int
+	mu       sync.Mutex // protects the following
+	// calls tracks the number of calls received.
+	calls map[string]int
+}
+
+func (m *mockHTTPClient) Do(req *http.Request) (*http.Response, error) {
+	m.mu.Lock()
+	if m.calls == nil {
+		m.calls = make(map[string]int)
+	}
+
+	endpoint := req.URL.String()
+	m.calls[endpoint]++
+	calls := m.calls[endpoint]
+	m.mu.Unlock()
+
+	resp := &http.Response{
+		StatusCode: http.StatusOK,
+		Header:     make(http.Header),
+		Body:       io.NopCloser(strings.NewReader("")),
+	}
+
+	if calls <= m.switches[endpoint] {
+		resp.Header.Set(kubetypes.PodIPv4Header, m.podIP) // Pod is still routable
+	} else {
+		resp.Header.Set(kubetypes.PodIPv4Header, m.anotherIP) // Pod is no longer routable
+	}
+	return resp, nil
+}

cmd/containerboot/settings.go

@@ -44,7 +44,6 @@ type settings struct {
 	DaemonExtraArgs               string
 	ExtraArgs                     string
 	InKubernetes                  bool
-	State                         string
 	UserspaceMode                 bool
 	StateDir                      string
 	AcceptDNS                     *bool
@@ -65,16 +64,16 @@ type settings struct {
 	// when setting up rules to proxy cluster traffic to cluster ingress
 	// target.
 	// Deprecated: use PodIPv4, PodIPv6 instead to support dual stack clusters
-	PodIP               string
-	PodIPv4             string
-	PodIPv6             string
-	PodUID              string
-	HealthCheckAddrPort string
-	LocalAddrPort       string
-	MetricsEnabled      bool
-	HealthCheckEnabled  bool
-	DebugAddrPort       string
-	EgressSvcsCfgPath   string
+	PodIP                string
+	PodIPv4              string
+	PodIPv6              string
+	PodUID               string
+	HealthCheckAddrPort  string
+	LocalAddrPort        string
+	MetricsEnabled       bool
+	HealthCheckEnabled   bool
+	DebugAddrPort        string
+	EgressProxiesCfgPath string
 }
 
 func configFromEnv() (*settings, error) {
@@ -90,7 +89,6 @@ func configFromEnv() (*settings, error) {
 		DaemonExtraArgs:                       defaultEnv("TS_TAILSCALED_EXTRA_ARGS", ""),
 		ExtraArgs:                             defaultEnv("TS_EXTRA_ARGS", ""),
 		InKubernetes:                          os.Getenv("KUBERNETES_SERVICE_HOST") != "",
-		State:                                 defaultEnv("TS_STATE", ""),
 		UserspaceMode:                         defaultBool("TS_USERSPACE", true),
 		StateDir:                              defaultEnv("TS_STATE_DIR", ""),
 		AcceptDNS:                             defaultEnvBoolPointer("TS_ACCEPT_DNS"),
@@ -109,22 +107,9 @@ func configFromEnv() (*settings, error) {
 		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", ""),
+		EgressProxiesCfgPath:                  defaultEnv("TS_EGRESS_PROXIES_CONFIG_PATH", ""),
 		PodUID:                                defaultEnv("POD_UID", ""),
 	}
-
-	if cfg.State == "" {
-		if cfg.InKubernetes && cfg.KubeSecret != "" {
-			cfg.State = "kube:" + cfg.KubeSecret
-		} else {
-			cfg.State = "mem:"
-		}
-	}
-
-	if !strings.HasPrefix(cfg.State, "mem:") && !strings.HasPrefix(cfg.State, "kube:") && !strings.HasPrefix(cfg.State, "ssm:") {
-		return nil, fmt.Errorf("invalid TS_STATE value %q; must start with 'mem:', 'kube:', or 'ssm:'", cfg.State)
-	}
-
 	podIPs, ok := os.LookupEnv("POD_IPS")
 	if ok {
 		ips := strings.Split(podIPs, ",")
@@ -150,35 +135,6 @@ func configFromEnv() (*settings, error) {
 }
 
 func (s *settings) validate() error {
-
-	// Validate TS_STATE if set
-	if s.State != "" {
-		if !strings.HasPrefix(s.State, "mem:") && 
-		   !strings.HasPrefix(s.State, "kube:") && 
-		   !strings.HasPrefix(s.State, "ssm:") {
-			return fmt.Errorf("invalid TS_STATE value %q; must start with 'mem:', 'kube:', or 'ssm:'", s.State)
-		}
-
-		if strings.HasPrefix(s.State, "kube:") && !s.InKubernetes {
-			return fmt.Errorf("TS_STATE specifies Kubernetes state but the runtime environment is not Kubernetes")
-		}
-	}
-
-	// Check legacy settings and ensure no conflicts if TS_STATE is set
-	if s.State != "" {
-		if s.KubeSecret != "" {
-			log.Printf("[warning] TS_STATE is set; ignoring legacy TS_KUBE_SECRET")
-		}
-		if s.StateDir != "" {
-			log.Printf("[warning] TS_STATE is set; ignoring legacy TS_STATE_DIR")
-		}
-	} else {
-		// Fallback to legacy checks if TS_STATE is not set
-		if s.KubeSecret != "" && !s.InKubernetes {
-			return fmt.Errorf("TS_KUBE_SECRET is set but the runtime environment is not Kubernetes")
-		}
-	}
-
 	if s.TailscaledConfigFilePath != "" {
 		dir, file := path.Split(s.TailscaledConfigFilePath)
 		if _, err := os.Stat(dir); err != nil {
@@ -230,7 +186,7 @@ func (s *settings) validate() error {
 			return fmt.Errorf("error parsing TS_HEALTHCHECK_ADDR_PORT value %q: %w", s.HealthCheckAddrPort, err)
 		}
 	}
-	if s.localMetricsEnabled() || s.localHealthEnabled() {
+	if s.localMetricsEnabled() || s.localHealthEnabled() || s.EgressProxiesCfgPath != "" {
 		if _, err := netip.ParseAddrPort(s.LocalAddrPort); err != nil {
 			return fmt.Errorf("error parsing TS_LOCAL_ADDR_PORT value %q: %w", s.LocalAddrPort, err)
 		}
@@ -243,10 +199,9 @@ func (s *settings) validate() error {
 	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")
+	if s.EgressProxiesCfgPath != "" && !(s.InKubernetes && s.KubeSecret != "") {
+		return errors.New("TS_EGRESS_PROXIES_CONFIG_PATH is only supported for Tailscale running on Kubernetes")
 	}
-	
 	return nil
 }
 
@@ -336,7 +291,7 @@ func isOneStepConfig(cfg *settings) bool {
 // as an L3 proxy, proxying to an endpoint provided via one of the config env
 // vars.
 func isL3Proxy(cfg *settings) bool {
-	return cfg.ProxyTargetIP != "" || cfg.ProxyTargetDNSName != "" || cfg.TailnetTargetIP != "" || cfg.TailnetTargetFQDN != "" || cfg.AllowProxyingClusterTrafficViaIngress || cfg.EgressSvcsCfgPath != ""
+	return cfg.ProxyTargetIP != "" || cfg.ProxyTargetDNSName != "" || cfg.TailnetTargetIP != "" || cfg.TailnetTargetFQDN != "" || cfg.AllowProxyingClusterTrafficViaIngress || cfg.EgressProxiesCfgPath != ""
 }
 
 // hasKubeStateStore returns true if the state must be stored in a Kubernetes
@@ -353,6 +308,10 @@ func (cfg *settings) localHealthEnabled() bool {
 	return cfg.LocalAddrPort != "" && cfg.HealthCheckEnabled
 }
 
+func (cfg *settings) egressSvcsTerminateEPEnabled() bool {
+	return cfg.LocalAddrPort != "" && cfg.EgressProxiesCfgPath != ""
+}
+
 // 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"
 )
 
@@ -39,14 +42,14 @@ func startTailscaled(ctx context.Context, cfg *settings) (*tailscale.LocalClient
 	log.Printf("Waiting for tailscaled socket")
 	for {
 		if ctx.Err() != nil {
-			log.Fatalf("Timed out waiting for tailscaled socket")
+			return nil, nil, errors.New("timed out waiting for tailscaled socket")
 		}
 		_, err := os.Stat(cfg.Socket)
 		if errors.Is(err, fs.ErrNotExist) {
 			time.Sleep(100 * time.Millisecond)
 			continue
 		} else if err != nil {
-			log.Fatalf("Waiting for tailscaled socket: %v", err)
+			return nil, nil, fmt.Errorf("error waiting for tailscaled socket: %w", err)
 		}
 		break
 	}
@@ -62,22 +65,17 @@ func startTailscaled(ctx context.Context, cfg *settings) (*tailscale.LocalClient
 // tailscaledArgs uses cfg to construct the argv for tailscaled.
 func tailscaledArgs(cfg *settings) []string {
 	args := []string{"--socket=" + cfg.Socket}
-	if cfg.State != "" {
-		args = append(args, "--state="+cfg.State)
-	} else {
-		// Fallback logic for legacy state configuration
-		switch {
-		case cfg.InKubernetes && cfg.KubeSecret != "":
-			args = append(args, "--state=kube:"+cfg.KubeSecret)
-			if cfg.StateDir == "" {
-				cfg.StateDir = "/tmp"
-			}
-			fallthrough
-		case cfg.StateDir != "":
-			args = append(args, "--statedir="+cfg.StateDir)
-		default:
-			args = append(args, "--state=mem:", "--statedir=/tmp")
+	switch {
+	case cfg.InKubernetes && cfg.KubeSecret != "":
+		args = append(args, "--state=kube:"+cfg.KubeSecret)
+		if cfg.StateDir == "" {
+			cfg.StateDir = "/tmp"
 		}
+		fallthrough
+	case cfg.StateDir != "":
+		args = append(args, "--statedir="+cfg.StateDir)
+	default:
+		args = append(args, "--state=mem:", "--statedir=/tmp")
 	}
 
 	if cfg.UserspaceMode {
@@ -171,3 +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/depaware.txt

@@ -28,7 +28,6 @@ tailscale.com/cmd/derper dependencies: (generated by github.com/tailscale/depawa
    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/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+
@@ -36,11 +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
@@ -86,7 +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+
@@ -100,6 +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+
@@ -189,6 +189,8 @@ tailscale.com/cmd/derper dependencies: (generated by github.com/tailscale/depawa
         golang.org/x/crypto/cryptobyte/asn1                          from crypto/ecdsa+
         golang.org/x/crypto/curve25519                               from golang.org/x/crypto/nacl/box+
         golang.org/x/crypto/hkdf                                     from crypto/tls+
+        golang.org/x/crypto/internal/alias                           from golang.org/x/crypto/chacha20+
+        golang.org/x/crypto/internal/poly1305                        from golang.org/x/crypto/chacha20poly1305+
         golang.org/x/crypto/nacl/box                                 from tailscale.com/types/key
         golang.org/x/crypto/nacl/secretbox                           from golang.org/x/crypto/nacl/box
         golang.org/x/crypto/salsa20/salsa                            from golang.org/x/crypto/nacl/box+
@@ -201,10 +203,11 @@ tailscale.com/cmd/derper dependencies: (generated by github.com/tailscale/depawa
         golang.org/x/net/http/httpproxy                              from net/http+
         golang.org/x/net/http2/hpack                                 from net/http
         golang.org/x/net/idna                                        from golang.org/x/crypto/acme/autocert+
+        golang.org/x/net/internal/socks                              from golang.org/x/net/proxy
         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+
@@ -232,6 +235,18 @@ tailscale.com/cmd/derper dependencies: (generated by github.com/tailscale/depawa
         crypto/ed25519                                               from crypto/tls+
         crypto/elliptic                                              from crypto/ecdsa+
         crypto/hmac                                                  from crypto/tls+
+        crypto/internal/alias                                        from crypto/aes+
+        crypto/internal/bigmod                                       from crypto/ecdsa+
+        crypto/internal/boring                                       from crypto/aes+
+        crypto/internal/boring/bbig                                  from crypto/ecdsa+
+        crypto/internal/boring/sig                                   from crypto/internal/boring
+        crypto/internal/edwards25519                                 from crypto/ed25519
+        crypto/internal/edwards25519/field                           from crypto/ecdh+
+        crypto/internal/hpke                                         from crypto/tls
+        crypto/internal/mlkem768                                     from crypto/tls
+        crypto/internal/nistec                                       from crypto/ecdh+
+        crypto/internal/nistec/fiat                                  from crypto/internal/nistec
+        crypto/internal/randutil                                     from crypto/dsa+
         crypto/md5                                                   from crypto/tls+
         crypto/rand                                                  from crypto/ed25519+
         crypto/rc4                                                   from crypto/tls
@@ -242,6 +257,7 @@ tailscale.com/cmd/derper dependencies: (generated by github.com/tailscale/depawa
         crypto/subtle                                                from crypto/aes+
         crypto/tls                                                   from golang.org/x/crypto/acme+
         crypto/x509                                                  from crypto/tls+
+   D    crypto/x509/internal/macos                                   from crypto/x509
         crypto/x509/pkix                                             from crypto/x509+
         embed                                                        from crypto/internal/nistec+
         encoding                                                     from encoding/json+
@@ -263,9 +279,47 @@ tailscale.com/cmd/derper dependencies: (generated by github.com/tailscale/depawa
         hash/maphash                                                 from go4.org/mem
         html                                                         from net/http/pprof+
         html/template                                                from tailscale.com/cmd/derper
+        internal/abi                                                 from crypto/x509/internal/macos+
+        internal/asan                                                from syscall
+        internal/bisect                                              from internal/godebug
+        internal/bytealg                                             from bytes+
+        internal/byteorder                                           from crypto/aes+
+        internal/chacha8rand                                         from math/rand/v2+
+        internal/concurrent                                          from unique
+        internal/coverage/rtcov                                      from runtime
+        internal/cpu                                                 from crypto/aes+
+        internal/filepathlite                                        from os+
+        internal/fmtsort                                             from fmt+
+        internal/goarch                                              from crypto/aes+
+        internal/godebug                                             from crypto/tls+
+        internal/godebugs                                            from internal/godebug+
+        internal/goexperiment                                        from runtime
+        internal/goos                                                from crypto/x509+
+        internal/itoa                                                from internal/poll+
+        internal/msan                                                from syscall
+        internal/nettrace                                            from net+
+        internal/oserror                                             from io/fs+
+        internal/poll                                                from net+
+        internal/profile                                             from net/http/pprof
+        internal/profilerecord                                       from runtime+
+        internal/race                                                from internal/poll+
+        internal/reflectlite                                         from context+
+        internal/runtime/atomic                                      from internal/runtime/exithook+
+        internal/runtime/exithook                                    from runtime
+   L    internal/runtime/syscall                                     from runtime+
+        internal/singleflight                                        from net
+        internal/stringslite                                         from embed+
+        internal/syscall/execenv                                     from os+
+  LD    internal/syscall/unix                                        from crypto/rand+
+   W    internal/syscall/windows                                     from crypto/rand+
+   W    internal/syscall/windows/registry                            from mime+
+   W    internal/syscall/windows/sysdll                              from internal/syscall/windows+
+        internal/testlog                                             from os
+        internal/unsafeheader                                        from internal/reflectlite+
+        internal/weak                                                from unique
         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
@@ -282,6 +336,7 @@ tailscale.com/cmd/derper dependencies: (generated by github.com/tailscale/depawa
         net/http                                                     from expvar+
         net/http/httptrace                                           from net/http+
         net/http/internal                                            from net/http
+        net/http/internal/ascii                                      from net/http
         net/http/pprof                                               from tailscale.com/tsweb
         net/netip                                                    from go4.org/netipx+
         net/textproto                                                from golang.org/x/net/http/httpguts+
@@ -295,7 +350,10 @@ tailscale.com/cmd/derper dependencies: (generated by github.com/tailscale/depawa
         reflect                                                      from crypto/x509+
         regexp                                                       from github.com/coreos/go-iptables/iptables+
         regexp/syntax                                                from regexp
+        runtime                                                      from crypto/internal/nistec+
         runtime/debug                                                from github.com/prometheus/client_golang/prometheus+
+        runtime/internal/math                                        from runtime
+        runtime/internal/sys                                         from runtime
         runtime/metrics                                              from github.com/prometheus/client_golang/prometheus+
         runtime/pprof                                                from net/http/pprof
         runtime/trace                                                from net/http/pprof
@@ -314,3 +372,4 @@ tailscale.com/cmd/derper dependencies: (generated by github.com/tailscale/depawa
         unicode/utf16                                                from crypto/x509+
         unicode/utf8                                                 from bufio+
         unique                                                       from net/netip
+        unsafe                                                       from bytes+

cmd/derper/derper.go

@@ -63,7 +63,7 @@ var (
 	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.")
@@ -77,6 +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 (
@@ -173,6 +175,7 @@ func main() {
 	s.SetVerifyClient(*verifyClients)
 	s.SetVerifyClientURL(*verifyClientURL)
 	s.SetVerifyClientURLFailOpen(*verifyFailOpen)
+	s.SetTCPWriteTimeout(*tcpWriteTimeout)
 
 	if *meshPSKFile != "" {
 		b, err := os.ReadFile(*meshPSKFile)

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

@@ -18,18 +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")
-	regionCode   = flag.String("region-code", "", "probe only this region (e.g. 'lax'); if left blank, all regions will be probed")
+	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() {
@@ -44,12 +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 *regionCode != "" {
-		opts = append(opts, prober.WithRegion(*regionCode))
+	if *regionCodeOrID != "" {
+		opts = append(opts, prober.WithRegionCodeOrID(*regionCodeOrID))
 	}
 	dp, err := prober.DERP(p, *derpMapURL, opts...)
 	if err != nil {
@@ -106,7 +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/k8s-operator/connector_test.go

@@ -79,8 +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"
@@ -106,7 +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) {
@@ -114,7 +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) {
@@ -122,7 +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) {
@@ -132,7 +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 {
@@ -175,8 +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) {
@@ -184,7 +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 {
@@ -203,7 +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"}}}},
 	}
@@ -261,8 +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
@@ -271,7 +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
@@ -286,7 +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
@@ -296,7 +296,7 @@ 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) {
@@ -351,8 +351,8 @@ func TestConnectorWithAppConnector(t *testing.T) {
 		app:            kubetypes.AppConnector,
 		isAppConnector: true,
 	}
-	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's ready condition should be set to true
 
 	cn.ObjectMeta.Finalizers = append(cn.ObjectMeta.Finalizers, "tailscale.com/finalizer")
@@ -364,7 +364,7 @@ func TestConnectorWithAppConnector(t *testing.T) {
 		Reason:             reasonConnectorCreated,
 		Message:            reasonConnectorCreated,
 	}}
-	expectEqual(t, fc, cn, nil)
+	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) {
@@ -379,7 +379,7 @@ func TestConnectorWithAppConnector(t *testing.T) {
 		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, nil)
+	expectEqual(t, fc, cn)
 
 	// 3. Connector with valid app connnector routes becomes ready
 	mustUpdate[tsapi.Connector](t, fc, "", "test", func(conn *tsapi.Connector) {

cmd/k8s-operator/depaware.txt

@@ -94,7 +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+
@@ -110,11 +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+
@@ -140,14 +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+
@@ -158,7 +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
@@ -172,7 +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+
@@ -187,7 +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
@@ -200,7 +197,6 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
    W 💣 github.com/tailscale/go-winio/internal/socket                from github.com/tailscale/go-winio
    W    github.com/tailscale/go-winio/internal/stringbuffer          from github.com/tailscale/go-winio/internal/fs
    W    github.com/tailscale/go-winio/pkg/guid                       from github.com/tailscale/go-winio+
-        github.com/tailscale/golang-x-crypto/acme                    from tailscale.com/ipn/ipnlocal
   LD    github.com/tailscale/golang-x-crypto/internal/poly1305       from github.com/tailscale/golang-x-crypto/ssh
   LD    github.com/tailscale/golang-x-crypto/ssh                     from tailscale.com/ipn/ipnlocal
   LD    github.com/tailscale/golang-x-crypto/ssh/internal/bcrypt_pbkdf from github.com/tailscale/golang-x-crypto/ssh
@@ -225,7 +221,6 @@ 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+
@@ -252,6 +247,7 @@ 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
@@ -277,8 +273,8 @@ 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
@@ -305,7 +301,7 @@ 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+
@@ -347,6 +343,7 @@ 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+
@@ -369,7 +366,8 @@ 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+
@@ -382,10 +380,12 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
         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+
@@ -397,6 +397,9 @@ 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+
@@ -448,6 +451,7 @@ 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
@@ -472,7 +476,8 @@ 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
@@ -482,8 +487,80 @@ 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
@@ -507,6 +584,7 @@ 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
@@ -529,7 +607,8 @@ 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
@@ -537,6 +616,56 @@ 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+
@@ -548,6 +677,7 @@ 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
@@ -564,11 +694,14 @@ 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
@@ -589,11 +722,12 @@ 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+
@@ -626,12 +760,12 @@ 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+
@@ -642,10 +776,10 @@ 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
@@ -666,6 +800,11 @@ 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/capture                                from tailscale.com/feature/condregister
+        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+
@@ -675,7 +814,7 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
      💣 tailscale.com/ipn/ipnauth                                    from tailscale.com/ipn/ipnlocal+
         tailscale.com/ipn/ipnlocal                                   from tailscale.com/ipn/localapi+
         tailscale.com/ipn/ipnstate                                   from tailscale.com/client/tailscale+
-        tailscale.com/ipn/localapi                                   from tailscale.com/tsnet
+        tailscale.com/ipn/localapi                                   from tailscale.com/tsnet+
         tailscale.com/ipn/policy                                     from tailscale.com/ipn/ipnlocal
         tailscale.com/ipn/store                                      from tailscale.com/ipn/ipnlocal+
    L    tailscale.com/ipn/store/awsstore                             from tailscale.com/ipn/store
@@ -700,6 +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+
@@ -747,7 +887,9 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
         tailscale.com/syncs                                          from tailscale.com/control/controlknobs+
         tailscale.com/tailcfg                                        from tailscale.com/client/tailscale+
         tailscale.com/taildrop                                       from tailscale.com/ipn/ipnlocal+
+        tailscale.com/tempfork/acme                                  from tailscale.com/ipn/ipnlocal
         tailscale.com/tempfork/heap                                  from tailscale.com/wgengine/magicsock
+        tailscale.com/tempfork/httprec                               from tailscale.com/control/controlclient
         tailscale.com/tka                                            from tailscale.com/client/tailscale+
         tailscale.com/tsconst                                        from tailscale.com/net/netmon+
         tailscale.com/tsd                                            from tailscale.com/ipn/ipnlocal+
@@ -818,7 +960,6 @@ 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+
@@ -830,7 +971,6 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
         tailscale.com/version                                        from tailscale.com/client/web+
         tailscale.com/version/distro                                 from tailscale.com/client/web+
         tailscale.com/wgengine                                       from tailscale.com/ipn/ipnlocal+
-        tailscale.com/wgengine/capture                               from tailscale.com/ipn/ipnlocal+
         tailscale.com/wgengine/filter                                from tailscale.com/control/controlclient+
         tailscale.com/wgengine/filter/filtertype                     from tailscale.com/types/netmap+
      💣 tailscale.com/wgengine/magicsock                             from tailscale.com/ipn/ipnlocal+
@@ -853,6 +993,8 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
         golang.org/x/crypto/cryptobyte/asn1                          from crypto/ecdsa+
         golang.org/x/crypto/curve25519                               from github.com/tailscale/golang-x-crypto/ssh+
         golang.org/x/crypto/hkdf                                     from crypto/tls+
+        golang.org/x/crypto/internal/alias                           from golang.org/x/crypto/chacha20+
+        golang.org/x/crypto/internal/poly1305                        from golang.org/x/crypto/chacha20poly1305+
         golang.org/x/crypto/nacl/box                                 from tailscale.com/types/key
         golang.org/x/crypto/nacl/secretbox                           from golang.org/x/crypto/nacl/box
         golang.org/x/crypto/poly1305                                 from github.com/tailscale/wireguard-go/device
@@ -870,6 +1012,10 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
         golang.org/x/net/http2/hpack                                 from golang.org/x/net/http2+
         golang.org/x/net/icmp                                        from github.com/prometheus-community/pro-bing+
         golang.org/x/net/idna                                        from golang.org/x/net/http/httpguts+
+        golang.org/x/net/internal/httpcommon                         from golang.org/x/net/http2
+        golang.org/x/net/internal/iana                               from golang.org/x/net/icmp+
+        golang.org/x/net/internal/socket                             from golang.org/x/net/icmp+
+        golang.org/x/net/internal/socks                              from golang.org/x/net/proxy
         golang.org/x/net/ipv4                                        from github.com/miekg/dns+
         golang.org/x/net/ipv6                                        from github.com/miekg/dns+
         golang.org/x/net/proxy                                       from tailscale.com/net/netns
@@ -879,7 +1025,7 @@ 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+
@@ -911,6 +1057,18 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
         crypto/ed25519                                               from crypto/tls+
         crypto/elliptic                                              from crypto/ecdsa+
         crypto/hmac                                                  from crypto/tls+
+        crypto/internal/alias                                        from crypto/aes+
+        crypto/internal/bigmod                                       from crypto/ecdsa+
+        crypto/internal/boring                                       from crypto/aes+
+        crypto/internal/boring/bbig                                  from crypto/ecdsa+
+        crypto/internal/boring/sig                                   from crypto/internal/boring
+        crypto/internal/edwards25519                                 from crypto/ed25519
+        crypto/internal/edwards25519/field                           from crypto/ecdh+
+        crypto/internal/hpke                                         from crypto/tls
+        crypto/internal/mlkem768                                     from crypto/tls
+        crypto/internal/nistec                                       from crypto/ecdh+
+        crypto/internal/nistec/fiat                                  from crypto/internal/nistec
+        crypto/internal/randutil                                     from crypto/dsa+
         crypto/md5                                                   from crypto/tls+
         crypto/rand                                                  from crypto/ed25519+
         crypto/rc4                                                   from crypto/tls+
@@ -921,6 +1079,7 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
         crypto/subtle                                                from crypto/aes+
         crypto/tls                                                   from github.com/aws/aws-sdk-go-v2/aws/transport/http+
         crypto/x509                                                  from crypto/tls+
+   D    crypto/x509/internal/macos                                   from crypto/x509
         crypto/x509/pkix                                             from crypto/x509+
         database/sql                                                 from github.com/prometheus/client_golang/prometheus/collectors
         database/sql/driver                                          from database/sql+
@@ -946,6 +1105,7 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
         go/build/constraint                                          from go/parser
         go/doc                                                       from k8s.io/apimachinery/pkg/runtime
         go/doc/comment                                               from go/doc
+        go/internal/typeparams                                       from go/parser
         go/parser                                                    from k8s.io/apimachinery/pkg/runtime
         go/scanner                                                   from go/ast+
         go/token                                                     from go/ast+
@@ -956,6 +1116,46 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
         hash/maphash                                                 from go4.org/mem
         html                                                         from html/template+
         html/template                                                from github.com/gorilla/csrf
+        internal/abi                                                 from crypto/x509/internal/macos+
+        internal/asan                                                from syscall
+        internal/bisect                                              from internal/godebug
+        internal/bytealg                                             from bytes+
+        internal/byteorder                                           from crypto/aes+
+        internal/chacha8rand                                         from math/rand/v2+
+        internal/concurrent                                          from unique
+        internal/coverage/rtcov                                      from runtime
+        internal/cpu                                                 from crypto/aes+
+        internal/filepathlite                                        from os+
+        internal/fmtsort                                             from fmt+
+        internal/goarch                                              from crypto/aes+
+        internal/godebug                                             from archive/tar+
+        internal/godebugs                                            from internal/godebug+
+        internal/goexperiment                                        from runtime
+        internal/goos                                                from crypto/x509+
+        internal/itoa                                                from internal/poll+
+        internal/lazyregexp                                          from go/doc
+        internal/msan                                                from syscall
+        internal/nettrace                                            from net+
+        internal/oserror                                             from io/fs+
+        internal/poll                                                from net+
+        internal/profile                                             from net/http/pprof
+        internal/profilerecord                                       from runtime+
+        internal/race                                                from internal/poll+
+        internal/reflectlite                                         from context+
+        internal/runtime/atomic                                      from internal/runtime/exithook+
+        internal/runtime/exithook                                    from runtime
+   L    internal/runtime/syscall                                     from runtime+
+        internal/saferio                                             from debug/pe+
+        internal/singleflight                                        from net
+        internal/stringslite                                         from embed+
+        internal/syscall/execenv                                     from os+
+  LD    internal/syscall/unix                                        from crypto/rand+
+   W    internal/syscall/windows                                     from crypto/rand+
+   W    internal/syscall/windows/registry                            from mime+
+   W    internal/syscall/windows/sysdll                              from internal/syscall/windows+
+        internal/testlog                                             from os
+        internal/unsafeheader                                        from internal/reflectlite+
+        internal/weak                                                from unique
         io                                                           from archive/tar+
         io/fs                                                        from archive/tar+
         io/ioutil                                                    from github.com/aws/aws-sdk-go-v2/aws/protocol/query+
@@ -964,6 +1164,7 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
         log/internal                                                 from log+
         log/slog                                                     from github.com/go-logr/logr+
         log/slog/internal                                            from log/slog
+        log/slog/internal/buffer                                     from log/slog
         maps                                                         from sigs.k8s.io/controller-runtime/pkg/predicate+
         math                                                         from archive/tar+
         math/big                                                     from crypto/dsa+
@@ -975,10 +1176,10 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
         mime/quotedprintable                                         from mime/multipart
         net                                                          from crypto/tls+
         net/http                                                     from expvar+
-        net/http/httptest                                            from tailscale.com/control/controlclient
         net/http/httptrace                                           from github.com/prometheus-community/pro-bing+
         net/http/httputil                                            from github.com/aws/smithy-go/transport/http+
         net/http/internal                                            from net/http+
+        net/http/internal/ascii                                      from net/http+
         net/http/pprof                                               from sigs.k8s.io/controller-runtime/pkg/manager+
         net/netip                                                    from github.com/gaissmai/bart+
         net/textproto                                                from github.com/aws/aws-sdk-go-v2/aws/signer/v4+
@@ -992,7 +1193,10 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
         reflect                                                      from archive/tar+
         regexp                                                       from github.com/aws/aws-sdk-go-v2/internal/endpoints+
         regexp/syntax                                                from regexp
+        runtime                                                      from archive/tar+
         runtime/debug                                                from github.com/aws/aws-sdk-go-v2/internal/sync/singleflight+
+        runtime/internal/math                                        from runtime
+        runtime/internal/sys                                         from runtime
         runtime/metrics                                              from github.com/prometheus/client_golang/prometheus+
         runtime/pprof                                                from net/http/pprof+
         runtime/trace                                                from net/http/pprof
@@ -1011,3 +1215,4 @@ tailscale.com/cmd/k8s-operator dependencies: (generated by github.com/tailscale/
         unicode/utf16                                                from crypto/x509+
         unicode/utf8                                                 from bufio+
         unique                                                       from net/netip
+        unsafe                                                       from bytes+

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

@@ -63,7 +63,10 @@ rules:
   verbs: ["create","delete","deletecollection","get","list","patch","update","watch"]
 - apiGroups: [""]
   resources: ["pods"]
-  verbs: ["get","list","watch"]
+  verbs: ["get","list","watch", "update"]
+- apiGroups: [""]
+  resources: ["pods/status"]
+  verbs: ["update"]
 - apiGroups: ["apps"]
   resources: ["statefulsets", "deployments"]
   verbs: ["create","delete","deletecollection","get","list","patch","update","watch"]

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

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
@@ -99,6 +99,16 @@ spec:
                         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
@@ -133,6 +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
@@ -416,7 +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
@@ -431,7 +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
@@ -588,7 +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
@@ -603,7 +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
@@ -761,7 +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
@@ -776,7 +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
@@ -933,7 +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
@@ -948,7 +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
@@ -1062,6 +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.
@@ -1160,6 +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.
@@ -1208,18 +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
@@ -1375,6 +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
@@ -1479,7 +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.
@@ -1699,6 +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
@@ -1803,7 +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. Currently the only supported type is egress.
+                    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
@@ -294,7 +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
@@ -476,7 +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
@@ -563,6 +563,16 @@ spec:
                                             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
@@ -592,6 +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.
@@ -874,7 +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
@@ -889,7 +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
@@ -1050,7 +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
@@ -1065,7 +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
@@ -1219,7 +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
@@ -1234,7 +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
@@ -1395,7 +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
@@ -1410,7 +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
@@ -1522,6 +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.
@@ -1627,6 +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.
@@ -1675,18 +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
@@ -1837,6 +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
@@ -1945,7 +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.
@@ -2161,6 +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
@@ -2269,7 +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.
@@ -2703,7 +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
@@ -2721,9 +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: |-
@@ -2767,6 +2844,7 @@ spec:
                                     Replicas specifies how many replicas to create the StatefulSet with.
                                     Defaults to 2.
                                 format: int32
+                                minimum: 0
                                 type: integer
                             tags:
                                 description: |-
@@ -2781,10 +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. Currently the only supported type is egress.
+                                    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
@@ -2891,7 +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
@@ -2916,6 +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: |-
@@ -3239,7 +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
@@ -3254,7 +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
@@ -3415,7 +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
@@ -3430,7 +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
@@ -3584,7 +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
@@ -3599,7 +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
@@ -3760,7 +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
@@ -3775,7 +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
@@ -3937,6 +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
@@ -4040,7 +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.
@@ -4277,6 +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.
@@ -4325,18 +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
@@ -4722,6 +4854,13 @@ rules:
         - get
         - list
         - watch
+        - update
+    - apiGroups:
+        - ""
+      resources:
+        - pods/status
+      verbs:
+        - update
     - apiGroups:
         - apps
       resources:

cmd/k8s-operator/egress-eps.go

@@ -20,7 +20,6 @@ import (
 	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
 	"sigs.k8s.io/controller-runtime/pkg/client"
 	"sigs.k8s.io/controller-runtime/pkg/reconcile"
-	tsoperator "tailscale.com/k8s-operator"
 	"tailscale.com/kube/egressservices"
 	"tailscale.com/types/ptr"
 )
@@ -71,25 +70,27 @@ func (er *egressEpsReconciler) Reconcile(ctx context.Context, req reconcile.Requ
 	if err != nil {
 		return res, fmt.Errorf("error retrieving ExternalName Service: %w", err)
 	}
-	if !tsoperator.EgressServiceIsValidAndConfigured(svc) {
-		l.Infof("Cluster resources for ExternalName Service %s/%s are not yet configured", svc.Namespace, svc.Name)
-		return res, nil
-	}
 
 	// TODO(irbekrm): currently this reconcile loop runs all the checks every time it's triggered, which is
 	// wasteful. Once we have a Ready condition for ExternalName Services for ProxyGroup, use the condition to
 	// determine if a reconcile is needed.
 
 	oldEps := eps.DeepCopy()
-	proxyGroupName := eps.Labels[labelProxyGroup]
 	tailnetSvc := tailnetSvcName(svc)
 	l = l.With("tailnet-service-name", tailnetSvc)
 
 	// Retrieve the desired tailnet service configuration from the ConfigMap.
+	proxyGroupName := eps.Labels[labelProxyGroup]
 	_, cfgs, err := egressSvcsConfigs(ctx, er.Client, proxyGroupName, er.tsNamespace)
 	if err != nil {
 		return res, fmt.Errorf("error retrieving tailnet services configuration: %w", err)
 	}
+	if cfgs == nil {
+		// TODO(irbekrm): this path would be hit if egress service was once exposed on a ProxyGroup that later
+		// got deleted. Probably the EndpointSlices then need to be deleted too- need to rethink this flow.
+		l.Debugf("No egress config found, likely because ProxyGroup has not been created")
+		return res, nil
+	}
 	cfg, ok := (*cfgs)[tailnetSvc]
 	if !ok {
 		l.Infof("[unexpected] configuration for tailnet service %s not found", tailnetSvc)

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-pod-readiness.go

@@ -0,0 +1,274 @@
+// Copyright (c) Tailscale Inc & AUTHORS
+// SPDX-License-Identifier: BSD-3-Clause
+
+//go:build !plan9
+
+package main
+
+import (
+	"context"
+	"errors"
+	"fmt"
+	"net/http"
+	"slices"
+	"strings"
+	"sync/atomic"
+	"time"
+
+	"go.uber.org/zap"
+	xslices "golang.org/x/exp/slices"
+	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/types"
+	"sigs.k8s.io/controller-runtime/pkg/client"
+	"sigs.k8s.io/controller-runtime/pkg/reconcile"
+	tsapi "tailscale.com/k8s-operator/apis/v1alpha1"
+	"tailscale.com/kube/kubetypes"
+	"tailscale.com/logtail/backoff"
+	"tailscale.com/tstime"
+	"tailscale.com/util/httpm"
+)
+
+const tsEgressReadinessGate = "tailscale.com/egress-services"
+
+// egressPodsReconciler is responsible for setting tailscale.com/egress-services condition on egress ProxyGroup Pods.
+// The condition is used as a readiness gate for the Pod, meaning that kubelet will not mark the Pod as ready before the
+// condition is set. The ProxyGroup StatefulSet updates are rolled out in such a way that no Pod is restarted, before
+// the previous Pod is marked as ready, so ensuring that the Pod does not get marked as ready when it is not yet able to
+// route traffic for egress service prevents downtime during restarts caused by no available endpoints left because
+// every Pod has been recreated and is not yet added to endpoints.
+// https://kubernetes.io/docs/concepts/workloads/pods/pod-lifecycle/#pod-readiness-gate
+type egressPodsReconciler struct {
+	client.Client
+	logger      *zap.SugaredLogger
+	tsNamespace string
+	clock       tstime.Clock
+	httpClient  doer          // http client that can be set to a mock client in tests
+	maxBackoff  time.Duration // max backoff period between health check calls
+}
+
+// Reconcile reconciles an egress ProxyGroup Pods on changes to those Pods and ProxyGroup EndpointSlices. It ensures
+// that for each Pod who is ready to route traffic to all egress services for the ProxyGroup, the Pod has a
+// tailscale.com/egress-services condition to set, so that kubelet will mark the Pod as ready.
+//
+// For the Pod to be ready
+// to route traffic to the egress service, the kube proxy needs to have set up the Pod's IP as an endpoint for the
+// ClusterIP Service corresponding to the egress service.
+//
+// Note that the endpoints for the ClusterIP Service are configured by the operator itself using custom
+// EndpointSlices(egress-eps-reconciler), so the routing is not blocked on Pod's readiness.
+//
+// Each egress service has a corresponding ClusterIP Service, that exposes all user configured
+// tailnet ports, as well as a health check port for the proxy.
+//
+// The reconciler calls the health check endpoint of each Service up to N number of times, where N is the number of
+// replicas for the ProxyGroup x 3, and checks if the received response is healthy response from the Pod being reconciled.
+//
+// The health check response contains a header with the
+// Pod's IP address- this is used to determine whether the response is received from this Pod.
+//
+// If the Pod does not appear to be serving the health check endpoint (pre-v1.80 proxies), the reconciler just sets the
+// readiness condition for backwards compatibility reasons.
+func (er *egressPodsReconciler) Reconcile(ctx context.Context, req reconcile.Request) (res reconcile.Result, err error) {
+	l := er.logger.With("Pod", req.NamespacedName)
+	l.Debugf("starting reconcile")
+	defer l.Debugf("reconcile finished")
+
+	pod := new(corev1.Pod)
+	err = er.Get(ctx, req.NamespacedName, pod)
+	if apierrors.IsNotFound(err) {
+		return reconcile.Result{}, nil
+	}
+	if err != nil {
+		return reconcile.Result{}, fmt.Errorf("failed to get Pod: %w", err)
+	}
+	if !pod.DeletionTimestamp.IsZero() {
+		l.Debugf("Pod is being deleted, do nothing")
+		return res, nil
+	}
+	if pod.Labels[LabelParentType] != proxyTypeProxyGroup {
+		l.Infof("[unexpected] reconciler called for a Pod that is not a ProxyGroup Pod")
+		return res, nil
+	}
+
+	// If the Pod does not have the readiness gate set, there is no need to add the readiness condition. In practice
+	// this will happen if the user has configured custom TS_LOCAL_ADDR_PORT, thus disabling the graceful failover.
+	if !slices.ContainsFunc(pod.Spec.ReadinessGates, func(r corev1.PodReadinessGate) bool {
+		return r.ConditionType == tsEgressReadinessGate
+	}) {
+		l.Debug("Pod does not have egress readiness gate set, skipping")
+		return res, nil
+	}
+
+	proxyGroupName := pod.Labels[LabelParentName]
+	pg := new(tsapi.ProxyGroup)
+	if err := er.Get(ctx, types.NamespacedName{Name: proxyGroupName}, pg); err != nil {
+		return res, fmt.Errorf("error getting ProxyGroup %q: %w", proxyGroupName, err)
+	}
+	if pg.Spec.Type != typeEgress {
+		l.Infof("[unexpected] reconciler called for %q ProxyGroup Pod", pg.Spec.Type)
+		return res, nil
+	}
+	// Get all ClusterIP Services for all egress targets exposed to cluster via this ProxyGroup.
+	lbls := map[string]string{
+		LabelManaged:    "true",
+		labelProxyGroup: proxyGroupName,
+		labelSvcType:    typeEgress,
+	}
+	svcs := &corev1.ServiceList{}
+	if err := er.List(ctx, svcs, client.InNamespace(er.tsNamespace), client.MatchingLabels(lbls)); err != nil {
+		return res, fmt.Errorf("error listing ClusterIP Services")
+	}
+
+	idx := xslices.IndexFunc(pod.Status.Conditions, func(c corev1.PodCondition) bool {
+		return c.Type == tsEgressReadinessGate
+	})
+	if idx != -1 {
+		l.Debugf("Pod is already ready, do nothing")
+		return res, nil
+	}
+
+	var routesMissing atomic.Bool
+	errChan := make(chan error, len(svcs.Items))
+	for _, svc := range svcs.Items {
+		s := svc
+		go func() {
+			ll := l.With("service_name", s.Name)
+			d := retrieveClusterDomain(er.tsNamespace, ll)
+			healthCheckAddr := healthCheckForSvc(&s, d)
+			if healthCheckAddr == "" {
+				ll.Debugf("ClusterIP Service does not expose a health check endpoint, unable to verify if routing is set up")
+				errChan <- nil
+				return
+			}
+
+			var routesSetup bool
+			bo := backoff.NewBackoff(s.Name, ll.Infof, er.maxBackoff)
+			for range numCalls(pgReplicas(pg)) {
+				if ctx.Err() != nil {
+					errChan <- nil
+					return
+				}
+				state, err := er.lookupPodRouteViaSvc(ctx, pod, healthCheckAddr, ll)
+				if err != nil {
+					errChan <- fmt.Errorf("error validating if routing has been set up for Pod: %w", err)
+					return
+				}
+				if state == healthy || state == cannotVerify {
+					routesSetup = true
+					break
+				}
+				if state == unreachable || state == unhealthy || state == podNotReady {
+					bo.BackOff(ctx, errors.New("backoff"))
+				}
+			}
+			if !routesSetup {
+				ll.Debugf("Pod is not yet configured as Service endpoint")
+				routesMissing.Store(true)
+			}
+			errChan <- nil
+		}()
+	}
+	for range len(svcs.Items) {
+		e := <-errChan
+		err = errors.Join(err, e)
+	}
+	if err != nil {
+		return res, fmt.Errorf("error verifying conectivity: %w", err)
+	}
+	if rm := routesMissing.Load(); rm {
+		l.Info("Pod is not yet added as an endpoint for all egress targets, waiting...")
+		return reconcile.Result{RequeueAfter: shortRequeue}, nil
+	}
+	if err := er.setPodReady(ctx, pod, l); err != nil {
+		return res, fmt.Errorf("error setting Pod as ready: %w", err)
+	}
+	return res, nil
+}
+
+func (er *egressPodsReconciler) setPodReady(ctx context.Context, pod *corev1.Pod, l *zap.SugaredLogger) error {
+	if slices.ContainsFunc(pod.Status.Conditions, func(c corev1.PodCondition) bool {
+		return c.Type == tsEgressReadinessGate
+	}) {
+		return nil
+	}
+	l.Infof("Pod is ready to route traffic to all egress targets")
+	pod.Status.Conditions = append(pod.Status.Conditions, corev1.PodCondition{
+		Type:               tsEgressReadinessGate,
+		Status:             corev1.ConditionTrue,
+		LastTransitionTime: metav1.Time{Time: er.clock.Now()},
+	})
+	return er.Status().Update(ctx, pod)
+}
+
+// healthCheckState is the result of a single request to an egress Service health check endpoint with a goal to hit a
+// specific backend Pod.
+type healthCheckState int8
+
+const (
+	cannotVerify healthCheckState = iota // not verifiable for this setup (i.e earlier proxy version)
+	unreachable                          // no backends or another network error
+	notFound                             // hit another backend
+	unhealthy                            // not 200
+	podNotReady                          // Pod is not ready, i.e does not have an IP address yet
+	healthy                              // 200
+)
+
+// lookupPodRouteViaSvc attempts to reach a Pod using a health check endpoint served by a Service and returns the state of the health check.
+func (er *egressPodsReconciler) lookupPodRouteViaSvc(ctx context.Context, pod *corev1.Pod, healthCheckAddr string, l *zap.SugaredLogger) (healthCheckState, error) {
+	if !slices.ContainsFunc(pod.Spec.Containers[0].Env, func(e corev1.EnvVar) bool {
+		return e.Name == "TS_ENABLE_HEALTH_CHECK" && e.Value == "true"
+	}) {
+		l.Debugf("Pod does not have health check enabled, unable to verify if it is currently routable via Service")
+		return cannotVerify, nil
+	}
+	wantsIP, err := podIPv4(pod)
+	if err != nil {
+		return -1, fmt.Errorf("error determining Pod's IP address: %w", err)
+	}
+	if wantsIP == "" {
+		return podNotReady, nil
+	}
+
+	ctx, cancel := context.WithTimeout(ctx, time.Second*3)
+	defer cancel()
+	req, err := http.NewRequestWithContext(ctx, httpm.GET, healthCheckAddr, nil)
+	if err != nil {
+		return -1, fmt.Errorf("error creating new HTTP request: %w", err)
+	}
+	// Do not re-use the same connection for the next request so to maximize the chance of hitting all backends equally.
+	req.Close = true
+	resp, err := er.httpClient.Do(req)
+	if err != nil {
+		// This is most likely because this is the first Pod and is not yet added to Service endoints. Other
+		// error types are possible, but checking for those would likely make the system too fragile.
+		return unreachable, nil
+	}
+	defer resp.Body.Close()
+	gotIP := resp.Header.Get(kubetypes.PodIPv4Header)
+	if gotIP == "" {
+		l.Debugf("Health check does not return Pod's IP header, unable to verify if Pod is currently routable via Service")
+		return cannotVerify, nil
+	}
+	if !strings.EqualFold(wantsIP, gotIP) {
+		return notFound, nil
+	}
+	if resp.StatusCode != http.StatusOK {
+		return unhealthy, nil
+	}
+	return healthy, nil
+}
+
+// numCalls return the number of times an endpoint on a ProxyGroup Service should be called till it can be safely
+// assumed that, if none of the responses came back from a specific Pod then traffic for the Service is currently not
+// being routed to that Pod. This assumes that traffic for the Service is routed via round robin, so
+// InternalTrafficPolicy must be 'Cluster' and session affinity must be None.
+func numCalls(replicas int32) int32 {
+	return replicas * 3
+}
+
+// doer is an interface for HTTP client that can be set to a mock client in tests.
+type doer interface {
+	Do(*http.Request) (*http.Response, error)
+}

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

@@ -0,0 +1,525 @@
+// Copyright (c) Tailscale Inc & AUTHORS
+// SPDX-License-Identifier: BSD-3-Clause
+
+//go:build !plan9
+
+package main
+
+import (
+	"bytes"
+	"errors"
+	"fmt"
+	"io"
+	"log"
+	"net/http"
+	"sync"
+	"testing"
+	"time"
+
+	"go.uber.org/zap"
+	corev1 "k8s.io/api/core/v1"
+	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
+	"k8s.io/apimachinery/pkg/util/intstr"
+	"sigs.k8s.io/controller-runtime/pkg/client/fake"
+	tsapi "tailscale.com/k8s-operator/apis/v1alpha1"
+	"tailscale.com/kube/kubetypes"
+	"tailscale.com/tstest"
+	"tailscale.com/types/ptr"
+)
+
+func TestEgressPodReadiness(t *testing.T) {
+	// We need to pass a Pod object to WithStatusSubresource because of some quirks in how the fake client
+	// works. Without this code we would not be able to update Pod's status further down.
+	fc := fake.NewClientBuilder().
+		WithScheme(tsapi.GlobalScheme).
+		WithStatusSubresource(&corev1.Pod{}).
+		Build()
+	zl, _ := zap.NewDevelopment()
+	cl := tstest.NewClock(tstest.ClockOpts{})
+	rec := &egressPodsReconciler{
+		tsNamespace: "operator-ns",
+		Client:      fc,
+		logger:      zl.Sugar(),
+		clock:       cl,
+	}
+	pg := &tsapi.ProxyGroup{
+		ObjectMeta: metav1.ObjectMeta{
+			Name: "dev",
+		},
+		Spec: tsapi.ProxyGroupSpec{
+			Type:     "egress",
+			Replicas: ptr.To(int32(3)),
+		},
+	}
+	mustCreate(t, fc, pg)
+	podIP := "10.0.0.2"
+	podTemplate := &corev1.Pod{
+		ObjectMeta: metav1.ObjectMeta{
+			Namespace: "operator-ns",
+			Name:      "pod",
+			Labels: map[string]string{
+				LabelParentType: "proxygroup",
+				LabelParentName: "dev",
+			},
+		},
+		Spec: corev1.PodSpec{
+			ReadinessGates: []corev1.PodReadinessGate{{
+				ConditionType: tsEgressReadinessGate,
+			}},
+			Containers: []corev1.Container{{
+				Name: "tailscale",
+				Env: []corev1.EnvVar{{
+					Name:  "TS_ENABLE_HEALTH_CHECK",
+					Value: "true",
+				}},
+			}},
+		},
+		Status: corev1.PodStatus{
+			PodIPs: []corev1.PodIP{{IP: podIP}},
+		},
+	}
+
+	t.Run("no_egress_services", func(t *testing.T) {
+		pod := podTemplate.DeepCopy()
+		mustCreate(t, fc, pod)
+		expectReconciled(t, rec, "operator-ns", pod.Name)
+
+		// Pod should have readiness gate condition set.
+		podSetReady(pod, cl)
+		expectEqual(t, fc, pod)
+		mustDeleteAll(t, fc, pod)
+	})
+	t.Run("one_svc_already_routed_to", func(t *testing.T) {
+		pod := podTemplate.DeepCopy()
+
+		svc, hep := newSvc("svc", 9002)
+		mustCreateAll(t, fc, svc, pod)
+		resp := readyResps(podIP, 1)
+		httpCl := fakeHTTPClient{
+			t:     t,
+			state: map[string][]fakeResponse{hep: resp},
+		}
+		rec.httpClient = &httpCl
+		expectReconciled(t, rec, "operator-ns", pod.Name)
+
+		// Pod should have readiness gate condition set.
+		podSetReady(pod, cl)
+		expectEqual(t, fc, pod)
+
+		// A subsequent reconcile should not change the Pod.
+		expectReconciled(t, rec, "operator-ns", pod.Name)
+		expectEqual(t, fc, pod)
+
+		mustDeleteAll(t, fc, pod, svc)
+	})
+	t.Run("one_svc_many_backends_eventually_routed_to", func(t *testing.T) {
+		pod := podTemplate.DeepCopy()
+
+		svc, hep := newSvc("svc", 9002)
+		mustCreateAll(t, fc, svc, pod)
+		// For a 3 replica ProxyGroup the healthcheck endpoint should be called 9 times, make the 9th time only
+		// return with the right Pod IP.
+		resps := append(readyResps("10.0.0.3", 4), append(readyResps("10.0.0.4", 4), readyResps(podIP, 1)...)...)
+		httpCl := fakeHTTPClient{
+			t:     t,
+			state: map[string][]fakeResponse{hep: resps},
+		}
+		rec.httpClient = &httpCl
+		expectReconciled(t, rec, "operator-ns", pod.Name)
+
+		// Pod should have readiness gate condition set.
+		podSetReady(pod, cl)
+		expectEqual(t, fc, pod)
+		mustDeleteAll(t, fc, pod, svc)
+	})
+	t.Run("one_svc_one_backend_eventually_healthy", func(t *testing.T) {
+		pod := podTemplate.DeepCopy()
+
+		svc, hep := newSvc("svc", 9002)
+		mustCreateAll(t, fc, svc, pod)
+		// For a 3 replica ProxyGroup the healthcheck endpoint should be called 9 times, make the 9th time only
+		// return with 200 status code.
+		resps := append(unreadyResps(podIP, 8), readyResps(podIP, 1)...)
+		httpCl := fakeHTTPClient{
+			t:     t,
+			state: map[string][]fakeResponse{hep: resps},
+		}
+		rec.httpClient = &httpCl
+		expectReconciled(t, rec, "operator-ns", pod.Name)
+
+		// Pod should have readiness gate condition set.
+		podSetReady(pod, cl)
+		expectEqual(t, fc, pod)
+		mustDeleteAll(t, fc, pod, svc)
+	})
+	t.Run("one_svc_one_backend_never_routable", func(t *testing.T) {
+		pod := podTemplate.DeepCopy()
+
+		svc, hep := newSvc("svc", 9002)
+		mustCreateAll(t, fc, svc, pod)
+		// For a 3 replica ProxyGroup the healthcheck endpoint should be called 9 times and Pod should be
+		// requeued if neither of those succeed.
+		resps := readyResps("10.0.0.3", 9)
+		httpCl := fakeHTTPClient{
+			t:     t,
+			state: map[string][]fakeResponse{hep: resps},
+		}
+		rec.httpClient = &httpCl
+		expectRequeue(t, rec, "operator-ns", pod.Name)
+
+		// Pod should not have readiness gate condition set.
+		expectEqual(t, fc, pod)
+		mustDeleteAll(t, fc, pod, svc)
+	})
+	t.Run("one_svc_many_backends_already_routable", func(t *testing.T) {
+		pod := podTemplate.DeepCopy()
+
+		svc, hep := newSvc("svc", 9002)
+		svc2, hep2 := newSvc("svc-2", 9002)
+		svc3, hep3 := newSvc("svc-3", 9002)
+		mustCreateAll(t, fc, svc, svc2, svc3, pod)
+		resps := readyResps(podIP, 1)
+		httpCl := fakeHTTPClient{
+			t: t,
+			state: map[string][]fakeResponse{
+				hep:  resps,
+				hep2: resps,
+				hep3: resps,
+			},
+		}
+		rec.httpClient = &httpCl
+		expectReconciled(t, rec, "operator-ns", pod.Name)
+
+		// Pod should not have readiness gate condition set.
+		podSetReady(pod, cl)
+		expectEqual(t, fc, pod)
+		mustDeleteAll(t, fc, pod, svc, svc2, svc3)
+	})
+	t.Run("one_svc_many_backends_eventually_routable_and_healthy", func(t *testing.T) {
+		pod := podTemplate.DeepCopy()
+		svc, hep := newSvc("svc", 9002)
+		svc2, hep2 := newSvc("svc-2", 9002)
+		svc3, hep3 := newSvc("svc-3", 9002)
+		mustCreateAll(t, fc, svc, svc2, svc3, pod)
+		resps := append(readyResps("10.0.0.3", 7), readyResps(podIP, 1)...)
+		resps2 := append(readyResps("10.0.0.3", 5), readyResps(podIP, 1)...)
+		resps3 := append(unreadyResps(podIP, 4), readyResps(podIP, 1)...)
+		httpCl := fakeHTTPClient{
+			t: t,
+			state: map[string][]fakeResponse{
+				hep:  resps,
+				hep2: resps2,
+				hep3: resps3,
+			},
+		}
+		rec.httpClient = &httpCl
+		expectReconciled(t, rec, "operator-ns", pod.Name)
+
+		// Pod should have readiness gate condition set.
+		podSetReady(pod, cl)
+		expectEqual(t, fc, pod)
+		mustDeleteAll(t, fc, pod, svc, svc2, svc3)
+	})
+	t.Run("one_svc_many_backends_never_routable_and_healthy", func(t *testing.T) {
+		pod := podTemplate.DeepCopy()
+
+		svc, hep := newSvc("svc", 9002)
+		svc2, hep2 := newSvc("svc-2", 9002)
+		svc3, hep3 := newSvc("svc-3", 9002)
+		mustCreateAll(t, fc, svc, svc2, svc3, pod)
+		// For a ProxyGroup with 3 replicas, each Service's health endpoint will be tried 9 times and the Pod
+		// will be requeued if neither succeeds.
+		resps := readyResps("10.0.0.3", 9)
+		resps2 := append(readyResps("10.0.0.3", 5), readyResps("10.0.0.4", 4)...)
+		resps3 := unreadyResps(podIP, 9)
+		httpCl := fakeHTTPClient{
+			t: t,
+			state: map[string][]fakeResponse{
+				hep:  resps,
+				hep2: resps2,
+				hep3: resps3,
+			},
+		}
+		rec.httpClient = &httpCl
+		expectRequeue(t, rec, "operator-ns", pod.Name)
+
+		// Pod should not have readiness gate condition set.
+		expectEqual(t, fc, pod)
+		mustDeleteAll(t, fc, pod, svc, svc2, svc3)
+	})
+	t.Run("one_svc_many_backends_one_never_routable", func(t *testing.T) {
+		pod := podTemplate.DeepCopy()
+
+		svc, hep := newSvc("svc", 9002)
+		svc2, hep2 := newSvc("svc-2", 9002)
+		svc3, hep3 := newSvc("svc-3", 9002)
+		mustCreateAll(t, fc, svc, svc2, svc3, pod)
+		// For a ProxyGroup with 3 replicas, each Service's health endpoint will be tried 9 times and the Pod
+		// will be requeued if any one never succeeds.
+		resps := readyResps(podIP, 9)
+		resps2 := readyResps(podIP, 9)
+		resps3 := append(readyResps("10.0.0.3", 5), readyResps("10.0.0.4", 4)...)
+		httpCl := fakeHTTPClient{
+			t: t,
+			state: map[string][]fakeResponse{
+				hep:  resps,
+				hep2: resps2,
+				hep3: resps3,
+			},
+		}
+		rec.httpClient = &httpCl
+		expectRequeue(t, rec, "operator-ns", pod.Name)
+
+		// Pod should not have readiness gate condition set.
+		expectEqual(t, fc, pod)
+		mustDeleteAll(t, fc, pod, svc, svc2, svc3)
+	})
+	t.Run("one_svc_many_backends_one_never_healthy", func(t *testing.T) {
+		pod := podTemplate.DeepCopy()
+
+		svc, hep := newSvc("svc", 9002)
+		svc2, hep2 := newSvc("svc-2", 9002)
+		svc3, hep3 := newSvc("svc-3", 9002)
+		mustCreateAll(t, fc, svc, svc2, svc3, pod)
+		// For a ProxyGroup with 3 replicas, each Service's health endpoint will be tried 9 times and the Pod
+		// will be requeued if any one never succeeds.
+		resps := readyResps(podIP, 9)
+		resps2 := unreadyResps(podIP, 9)
+		resps3 := readyResps(podIP, 9)
+		httpCl := fakeHTTPClient{
+			t: t,
+			state: map[string][]fakeResponse{
+				hep:  resps,
+				hep2: resps2,
+				hep3: resps3,
+			},
+		}
+		rec.httpClient = &httpCl
+		expectRequeue(t, rec, "operator-ns", pod.Name)
+
+		// Pod should not have readiness gate condition set.
+		expectEqual(t, fc, pod)
+		mustDeleteAll(t, fc, pod, svc, svc2, svc3)
+	})
+	t.Run("one_svc_many_backends_different_ports_eventually_healthy_and_routable", func(t *testing.T) {
+		pod := podTemplate.DeepCopy()
+
+		svc, hep := newSvc("svc", 9003)
+		svc2, hep2 := newSvc("svc-2", 9004)
+		svc3, hep3 := newSvc("svc-3", 9010)
+		mustCreateAll(t, fc, svc, svc2, svc3, pod)
+		// For a ProxyGroup with 3 replicas, each Service's health endpoint will be tried up to 9 times and
+		// marked as success as soon as one try succeeds.
+		resps := append(readyResps("10.0.0.3", 7), readyResps(podIP, 1)...)
+		resps2 := append(readyResps("10.0.0.3", 5), readyResps(podIP, 1)...)
+		resps3 := append(unreadyResps(podIP, 4), readyResps(podIP, 1)...)
+		httpCl := fakeHTTPClient{
+			t: t,
+			state: map[string][]fakeResponse{
+				hep:  resps,
+				hep2: resps2,
+				hep3: resps3,
+			},
+		}
+		rec.httpClient = &httpCl
+		expectReconciled(t, rec, "operator-ns", pod.Name)
+
+		// Pod should have readiness gate condition set.
+		podSetReady(pod, cl)
+		expectEqual(t, fc, pod)
+		mustDeleteAll(t, fc, pod, svc, svc2, svc3)
+	})
+	// Proxies of 1.78 and earlier did not set the Pod IP header.
+	t.Run("pod_does_not_return_ip_header", func(t *testing.T) {
+		pod := podTemplate.DeepCopy()
+		pod.Name = "foo-bar"
+
+		svc, hep := newSvc("foo-bar", 9002)
+		mustCreateAll(t, fc, svc, pod)
+		// If a response does not contain Pod IP header, we assume that this is an earlier proxy version,
+		// readiness cannot be verified so the readiness gate is just set to true.
+		resps := unreadyResps("", 1)
+		httpCl := fakeHTTPClient{
+			t: t,
+			state: map[string][]fakeResponse{
+				hep: resps,
+			},
+		}
+		rec.httpClient = &httpCl
+		expectReconciled(t, rec, "operator-ns", pod.Name)
+
+		// Pod should have readiness gate condition set.
+		podSetReady(pod, cl)
+		expectEqual(t, fc, pod)
+		mustDeleteAll(t, fc, pod, svc)
+	})
+	t.Run("one_svc_one_backend_eventually_healthy_and_routable", func(t *testing.T) {
+		pod := podTemplate.DeepCopy()
+
+		svc, hep := newSvc("svc", 9002)
+		mustCreateAll(t, fc, svc, pod)
+		// If a response errors, it is probably because the Pod is not yet properly running, so retry.
+		resps := append(erroredResps(8), readyResps(podIP, 1)...)
+		httpCl := fakeHTTPClient{
+			t: t,
+			state: map[string][]fakeResponse{
+				hep: resps,
+			},
+		}
+		rec.httpClient = &httpCl
+		expectReconciled(t, rec, "operator-ns", pod.Name)
+
+		// Pod should have readiness gate condition set.
+		podSetReady(pod, cl)
+		expectEqual(t, fc, pod)
+		mustDeleteAll(t, fc, pod, svc)
+	})
+	t.Run("one_svc_one_backend_svc_does_not_have_health_port", func(t *testing.T) {
+		pod := podTemplate.DeepCopy()
+
+		// If a Service does not have health port set, we assume that it is not possible to determine Pod's
+		// readiness and set it to ready.
+		svc, _ := newSvc("svc", -1)
+		mustCreateAll(t, fc, svc, pod)
+		rec.httpClient = nil
+		expectReconciled(t, rec, "operator-ns", pod.Name)
+
+		// Pod should have readiness gate condition set.
+		podSetReady(pod, cl)
+		expectEqual(t, fc, pod)
+		mustDeleteAll(t, fc, pod, svc)
+	})
+	t.Run("error_setting_up_healthcheck", func(t *testing.T) {
+		pod := podTemplate.DeepCopy()
+		// This is not a realistic reason for error, but we are just testing the behaviour of a healthcheck
+		// lookup failing.
+		pod.Status.PodIPs = []corev1.PodIP{{IP: "not-an-ip"}}
+
+		svc, _ := newSvc("svc", 9002)
+		svc2, _ := newSvc("svc-2", 9002)
+		svc3, _ := newSvc("svc-3", 9002)
+		mustCreateAll(t, fc, svc, svc2, svc3, pod)
+		rec.httpClient = nil
+		expectError(t, rec, "operator-ns", pod.Name)
+
+		// Pod should not have readiness gate condition set.
+		expectEqual(t, fc, pod)
+		mustDeleteAll(t, fc, pod, svc, svc2, svc3)
+	})
+	t.Run("pod_does_not_have_an_ip_address", func(t *testing.T) {
+		pod := podTemplate.DeepCopy()
+		pod.Status.PodIPs = nil
+
+		svc, _ := newSvc("svc", 9002)
+		svc2, _ := newSvc("svc-2", 9002)
+		svc3, _ := newSvc("svc-3", 9002)
+		mustCreateAll(t, fc, svc, svc2, svc3, pod)
+		rec.httpClient = nil
+		expectRequeue(t, rec, "operator-ns", pod.Name)
+
+		// Pod should not have readiness gate condition set.
+		expectEqual(t, fc, pod)
+		mustDeleteAll(t, fc, pod, svc, svc2, svc3)
+	})
+}
+
+func readyResps(ip string, num int) (resps []fakeResponse) {
+	for range num {
+		resps = append(resps, fakeResponse{statusCode: 200, podIP: ip})
+	}
+	return resps
+}
+
+func unreadyResps(ip string, num int) (resps []fakeResponse) {
+	for range num {
+		resps = append(resps, fakeResponse{statusCode: 503, podIP: ip})
+	}
+	return resps
+}
+
+func erroredResps(num int) (resps []fakeResponse) {
+	for range num {
+		resps = append(resps, fakeResponse{err: errors.New("timeout")})
+	}
+	return resps
+}
+
+func newSvc(name string, port int32) (*corev1.Service, string) {
+	svc := &corev1.Service{
+		ObjectMeta: metav1.ObjectMeta{
+			Namespace: "operator-ns",
+			Name:      name,
+			Labels: map[string]string{
+				LabelManaged:    "true",
+				labelProxyGroup: "dev",
+				labelSvcType:    typeEgress,
+			},
+		},
+		Spec: corev1.ServiceSpec{},
+	}
+	if port != -1 {
+		svc.Spec.Ports = []corev1.ServicePort{
+			{
+				Name:       tsHealthCheckPortName,
+				Port:       port,
+				TargetPort: intstr.FromInt(9002),
+				Protocol:   "TCP",
+			},
+		}
+	}
+	return svc, fmt.Sprintf("http://%s.operator-ns.svc.cluster.local:%d/healthz", name, port)
+}
+
+func podSetReady(pod *corev1.Pod, cl *tstest.Clock) {
+	pod.Status.Conditions = append(pod.Status.Conditions, corev1.PodCondition{
+		Type:               tsEgressReadinessGate,
+		Status:             corev1.ConditionTrue,
+		LastTransitionTime: metav1.Time{Time: cl.Now().Truncate(time.Second)},
+	})
+}
+
+// fakeHTTPClient is a mock HTTP client with a preset map of request URLs to list of responses. When it receives a
+// request for a specific URL, it returns the preset response for that URL. It errors if an unexpected request is
+// received.
+type fakeHTTPClient struct {
+	t     *testing.T
+	mu    sync.Mutex // protects following
+	state map[string][]fakeResponse
+}
+
+func (f *fakeHTTPClient) Do(req *http.Request) (*http.Response, error) {
+	f.mu.Lock()
+	resps := f.state[req.URL.String()]
+	if len(resps) == 0 {
+		f.mu.Unlock()
+		log.Printf("\n\n\nURL %q\n\n\n", req.URL)
+		f.t.Fatalf("fakeHTTPClient received an unexpected request for %q", req.URL)
+	}
+	defer func() {
+		if len(resps) == 1 {
+			delete(f.state, req.URL.String())
+			f.mu.Unlock()
+			return
+		}
+		f.state[req.URL.String()] = f.state[req.URL.String()][1:]
+		f.mu.Unlock()
+	}()
+
+	resp := resps[0]
+	if resp.err != nil {
+		return nil, resp.err
+	}
+	r := http.Response{
+		StatusCode: resp.statusCode,
+		Header:     make(http.Header),
+		Body:       io.NopCloser(bytes.NewReader([]byte{})),
+	}
+	r.Header.Add(kubetypes.PodIPv4Header, resp.podIP)
+	return &r, nil
+}
+
+type fakeResponse struct {
+	err        error
+	statusCode int
+	podIP      string // for the Pod IP header
+}

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

@@ -48,11 +48,12 @@ type egressSvcsReadinessReconciler struct {
 // service to determine how many replicas are currently able to route traffic.
 func (esrr *egressSvcsReadinessReconciler) Reconcile(ctx context.Context, req reconcile.Request) (res reconcile.Result, err error) {
 	l := esrr.logger.With("Service", req.NamespacedName)
-	defer l.Info("reconcile finished")
+	l.Debugf("starting reconcile")
+	defer l.Debugf("reconcile finished")
 
 	svc := new(corev1.Service)
 	if err = esrr.Get(ctx, req.NamespacedName, svc); apierrors.IsNotFound(err) {
-		l.Info("Service not found")
+		l.Debugf("Service not found")
 		return res, nil
 	} else if err != nil {
 		return res, fmt.Errorf("failed to get Service: %w", err)
@@ -127,16 +128,16 @@ func (esrr *egressSvcsReadinessReconciler) Reconcile(ctx context.Context, req re
 			return res, err
 		}
 		if pod == nil {
-			l.Infof("[unexpected] ProxyGroup is ready, but replica %d was not found", i)
+			l.Warnf("[unexpected] ProxyGroup is ready, but replica %d was not found", i)
 			reason, msg = reasonClusterResourcesNotReady, reasonClusterResourcesNotReady
 			return res, nil
 		}
-		l.Infof("looking at Pod with IPs %v", pod.Status.PodIPs)
+		l.Debugf("looking at Pod with IPs %v", pod.Status.PodIPs)
 		ready := false
 		for _, ep := range eps.Endpoints {
-			l.Infof("looking at endpoint with addresses %v", ep.Addresses)
+			l.Debugf("looking at endpoint with addresses %v", ep.Addresses)
 			if endpointReadyForPod(&ep, pod, l) {
-				l.Infof("endpoint is ready for Pod")
+				l.Debugf("endpoint is ready for Pod")
 				ready = true
 				break
 			}
@@ -165,7 +166,7 @@ func (esrr *egressSvcsReadinessReconciler) Reconcile(ctx context.Context, req re
 func endpointReadyForPod(ep *discoveryv1.Endpoint, pod *corev1.Pod, l *zap.SugaredLogger) bool {
 	podIP, err := podIPv4(pod)
 	if err != nil {
-		l.Infof("[unexpected] error retrieving Pod's IPv4 address: %v", err)
+		l.Warnf("[unexpected] error retrieving Pod's IPv4 address: %v", err)
 		return false
 	}
 	// Currently we only ever set a single address on and Endpoint and nothing else is meant to modify this.

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

@@ -59,6 +59,8 @@ const (
 	maxPorts = 1000
 
 	indexEgressProxyGroup = ".metadata.annotations.egress-proxy-group"
+
+	tsHealthCheckPortName = "tailscale-health-check"
 )
 
 var gaugeEgressServices = clientmetric.NewGauge(kubetypes.MetricEgressServiceCount)
@@ -229,15 +231,16 @@ 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.
+				// We want to both preserve the user set port names for ease of debugging, but also
+				// ensure that we name all unnamed ports as the ClusterIP Service that we create will
+				// always have at least two ports.
 				// 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
+				if wantsPM.Name != "" {
+					clusterIPSvc.Spec.Ports[i].Name = wantsPM.Name
+				} else {
+					clusterIPSvc.Spec.Ports[i].Name = "tailscale-unnamed"
+				}
 				found = true
 				break
 			}
@@ -252,6 +255,12 @@ func (esr *egressSvcsReconciler) provision(ctx context.Context, proxyGroupName s
 	// ClusterIP Service produce new target port and add a portmapping to
 	// the ClusterIP Service.
 	for _, wantsPM := range svc.Spec.Ports {
+		// Because we add a healthcheck port of our own, we will always have at least two ports. That
+		// means that we cannot have ports with name not set.
+		// https://kubernetes.io/docs/concepts/services-networking/service/#multi-port-services
+		if wantsPM.Name == "" {
+			wantsPM.Name = "tailscale-unnamed"
+		}
 		found := false
 		for _, gotPM := range clusterIPSvc.Spec.Ports {
 			if wantsPM.Port == gotPM.Port && strings.EqualFold(string(wantsPM.Protocol), string(gotPM.Protocol)) {
@@ -278,6 +287,25 @@ func (esr *egressSvcsReconciler) provision(ctx context.Context, proxyGroupName s
 			})
 		}
 	}
+	var healthCheckPort int32 = defaultLocalAddrPort
+
+	for {
+		if !slices.ContainsFunc(svc.Spec.Ports, func(p corev1.ServicePort) bool {
+			return p.Port == healthCheckPort
+		}) {
+			break
+		}
+		healthCheckPort++
+		if healthCheckPort > 10002 {
+			return nil, false, fmt.Errorf("unable to find a free port for internal health check in range [9002, 10002]")
+		}
+	}
+	clusterIPSvc.Spec.Ports = append(clusterIPSvc.Spec.Ports, corev1.ServicePort{
+		Name:       tsHealthCheckPortName,
+		Port:       healthCheckPort,
+		TargetPort: intstr.FromInt(defaultLocalAddrPort),
+		Protocol:   "TCP",
+	})
 	if !reflect.DeepEqual(clusterIPSvc, oldClusterIPSvc) {
 		if clusterIPSvc, err = createOrUpdate(ctx, esr.Client, esr.tsNamespace, clusterIPSvc, func(svc *corev1.Service) {
 			svc.Labels = clusterIPSvc.Labels
@@ -320,7 +348,7 @@ func (esr *egressSvcsReconciler) provision(ctx context.Context, proxyGroupName s
 	}
 	tailnetSvc := tailnetSvcName(svc)
 	gotCfg := (*cfgs)[tailnetSvc]
-	wantsCfg := egressSvcCfg(svc, clusterIPSvc)
+	wantsCfg := egressSvcCfg(svc, clusterIPSvc, esr.tsNamespace, l)
 	if !reflect.DeepEqual(gotCfg, wantsCfg) {
 		l.Debugf("updating egress services ConfigMap %s", cm.Name)
 		mak.Set(cfgs, tailnetSvc, wantsCfg)
@@ -495,13 +523,6 @@ 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)
@@ -510,11 +531,34 @@ func (esr *egressSvcsReconciler) validateClusterResources(ctx context.Context, s
 		tsoperator.RemoveServiceCondition(svc, tsapi.EgressSvcConfigured)
 		return false, nil
 	}
+	if !tsoperator.ProxyGroupIsReady(pg) {
+		tsoperator.SetServiceCondition(svc, tsapi.EgressSvcValid, metav1.ConditionUnknown, reasonProxyGroupNotReady, reasonProxyGroupNotReady, esr.clock, l)
+		tsoperator.RemoveServiceCondition(svc, tsapi.EgressSvcConfigured)
+	}
+
 	l.Debugf("egress service is valid")
 	tsoperator.SetServiceCondition(svc, tsapi.EgressSvcValid, metav1.ConditionTrue, reasonEgressSvcValid, reasonEgressSvcValid, esr.clock, l)
 	return true, nil
 }
 
+func egressSvcCfg(externalNameSvc, clusterIPSvc *corev1.Service, ns string, l *zap.SugaredLogger) egressservices.Config {
+	d := retrieveClusterDomain(ns, l)
+	tt := tailnetTargetFromSvc(externalNameSvc)
+	hep := healthCheckForSvc(clusterIPSvc, d)
+	cfg := egressservices.Config{
+		TailnetTarget:       tt,
+		HealthCheckEndpoint: hep,
+	}
+	for _, svcPort := range clusterIPSvc.Spec.Ports {
+		if svcPort.Name == tsHealthCheckPortName {
+			continue // exclude healthcheck from egress svcs configs
+		}
+		pm := portMap(svcPort)
+		mak.Set(&cfg.Ports, pm, struct{}{})
+	}
+	return cfg
+}
+
 func validateEgressService(svc *corev1.Service, pg *tsapi.ProxyGroup) []string {
 	violations := validateService(svc)
 
@@ -584,16 +628,6 @@ func tailnetTargetFromSvc(svc *corev1.Service) egressservices.TailnetTarget {
 	}
 }
 
-func egressSvcCfg(externalNameSvc, clusterIPSvc *corev1.Service) egressservices.Config {
-	tt := tailnetTargetFromSvc(externalNameSvc)
-	cfg := egressservices.Config{TailnetTarget: tt}
-	for _, svcPort := range clusterIPSvc.Spec.Ports {
-		pm := portMap(svcPort)
-		mak.Set(&cfg.Ports, pm, struct{}{})
-	}
-	return cfg
-}
-
 func portMap(p corev1.ServicePort) egressservices.PortMap {
 	// TODO (irbekrm): out of bounds check?
 	return egressservices.PortMap{Protocol: string(p.Protocol), MatchPort: uint16(p.TargetPort.IntVal), TargetPort: uint16(p.Port)}
@@ -618,7 +652,11 @@ func egressSvcsConfigs(ctx context.Context, cl client.Client, proxyGroupName, ts
 			Namespace: tsNamespace,
 		},
 	}
-	if err := cl.Get(ctx, client.ObjectKeyFromObject(cm), cm); err != nil {
+	err = cl.Get(ctx, client.ObjectKeyFromObject(cm), cm)
+	if apierrors.IsNotFound(err) { // ProxyGroup resources have not been created (yet)
+		return nil, nil, nil
+	}
+	if err != nil {
 		return nil, nil, fmt.Errorf("error retrieving egress services ConfigMap %s: %v", name, err)
 	}
 	cfgs = &egressservices.Configs{}
@@ -740,3 +778,17 @@ func (esr *egressSvcsReconciler) updateSvcSpec(ctx context.Context, svc *corev1.
 	svc.Status = *st
 	return err
 }
+
+// healthCheckForSvc return the URL of the containerboot's health check endpoint served by this Service or empty string.
+func healthCheckForSvc(svc *corev1.Service, clusterDomain string) string {
+	// This version of the operator always sets health check port on the egress Services. However, it is possible
+	// that this reconcile loops runs during a proxy upgrade from a version that did not set the health check port
+	// and parses a Service that does not have the port set yet.
+	i := slices.IndexFunc(svc.Spec.Ports, func(port corev1.ServicePort) bool {
+		return port.Name == tsHealthCheckPortName
+	})
+	if i == -1 {
+		return ""
+	}
+	return fmt.Sprintf("http://%s.%s.svc.%s:%d/healthz", svc.Name, svc.Namespace, clusterDomain, svc.Spec.Ports[i].Port)
+}

cmd/k8s-operator/egress-services_test.go

@@ -18,6 +18,7 @@ import (
 	discoveryv1 "k8s.io/api/discovery/v1"
 	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
 	"k8s.io/apimachinery/pkg/types"
+	"k8s.io/apimachinery/pkg/util/intstr"
 	"sigs.k8s.io/controller-runtime/pkg/client"
 	"sigs.k8s.io/controller-runtime/pkg/client/fake"
 	tsapi "tailscale.com/k8s-operator/apis/v1alpha1"
@@ -78,42 +79,16 @@ func TestTailscaleEgressServices(t *testing.T) {
 			Selector:     nil,
 			Ports: []corev1.ServicePort{
 				{
-					Name:     "http",
 					Protocol: "TCP",
 					Port:     80,
 				},
-				{
-					Name:     "https",
-					Protocol: "TCP",
-					Port:     443,
-				},
 			},
 		},
 	}
 
-	t.Run("proxy_group_not_ready", func(t *testing.T) {
+	t.Run("service_one_unnamed_port", func(t *testing.T) {
 		mustCreate(t, fc, svc)
 		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)
-	})
-
-	t.Run("proxy_group_ready", func(t *testing.T) {
-		mustUpdateStatus(t, fc, "", "foo", func(pg *tsapi.ProxyGroup) {
-			pg.Status.Conditions = []metav1.Condition{
-				condition(tsapi.ProxyGroupReady, metav1.ConditionTrue, "", "", clock),
-			}
-		})
-		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")
 		validateReadyService(t, fc, esr, svc, clock, zl, cm)
 	})
 	t.Run("service_add_two_named_ports", func(t *testing.T) {
@@ -162,9 +137,9 @@ func validateReadyService(t *testing.T, fc client.WithWatch, esr *egressSvcsReco
 	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)
+	expectEqual(t, fc, endpointSlice(name, svc, clusterSvc))
 	// Verify that ConfigMap contains configuration for the new egress service.
-	mustHaveConfigForSvc(t, fc, svc, clusterSvc, cm)
+	mustHaveConfigForSvc(t, fc, svc, clusterSvc, cm, zl)
 	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.
@@ -174,7 +149,7 @@ func validateReadyService(t *testing.T, fc client.WithWatch, esr *egressSvcsReco
 	}
 	svc.ObjectMeta.Finalizers = []string{"tailscale.com/finalizer"}
 	svc.Spec.ExternalName = fmt.Sprintf("%s.operator-ns.svc.cluster.local", name)
-	expectEqual(t, fc, svc, nil)
+	expectEqual(t, fc, svc)
 
 }
 
@@ -203,6 +178,23 @@ func findGenNameForEgressSvcResources(t *testing.T, client client.Client, svc *c
 
 func clusterIPSvc(name string, extNSvc *corev1.Service) *corev1.Service {
 	labels := egressSvcChildResourceLabels(extNSvc)
+	ports := make([]corev1.ServicePort, len(extNSvc.Spec.Ports))
+	for i, port := range extNSvc.Spec.Ports {
+		ports[i] = corev1.ServicePort{ // Copy the port to avoid modifying the original.
+			Name:     port.Name,
+			Port:     port.Port,
+			Protocol: port.Protocol,
+		}
+		if port.Name == "" {
+			ports[i].Name = "tailscale-unnamed"
+		}
+	}
+	ports = append(ports, corev1.ServicePort{
+		Name:       "tailscale-health-check",
+		Port:       9002,
+		TargetPort: intstr.FromInt(9002),
+		Protocol:   "TCP",
+	})
 	return &corev1.Service{
 		ObjectMeta: metav1.ObjectMeta{
 			Name:         name,
@@ -212,7 +204,7 @@ func clusterIPSvc(name string, extNSvc *corev1.Service) *corev1.Service {
 		},
 		Spec: corev1.ServiceSpec{
 			Type:  corev1.ServiceTypeClusterIP,
-			Ports: extNSvc.Spec.Ports,
+			Ports: ports,
 		},
 	}
 }
@@ -257,9 +249,9 @@ func portsForEndpointSlice(svc *corev1.Service) []discoveryv1.EndpointPort {
 	return ports
 }
 
-func mustHaveConfigForSvc(t *testing.T, cl client.Client, extNSvc, clusterIPSvc *corev1.Service, cm *corev1.ConfigMap) {
+func mustHaveConfigForSvc(t *testing.T, cl client.Client, extNSvc, clusterIPSvc *corev1.Service, cm *corev1.ConfigMap, l *zap.Logger) {
 	t.Helper()
-	wantsCfg := egressSvcCfg(extNSvc, clusterIPSvc)
+	wantsCfg := egressSvcCfg(extNSvc, clusterIPSvc, clusterIPSvc.Namespace, l.Sugar())
 	if err := cl.Get(context.Background(), client.ObjectKeyFromObject(cm), cm); err != nil {
 		t.Fatalf("Error retrieving ConfigMap: %v", err)
 	}

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")
 
@@ -128,9 +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,
@@ -159,7 +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")
 	}
 
@@ -185,73 +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")
@@ -263,10 +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,
@@ -322,28 +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

@@ -103,9 +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.
@@ -120,7 +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
@@ -129,7 +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) {
@@ -229,9 +229,9 @@ func TestTailscaleIngressHostname(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 proxy with capability version >= 110 does not have an HTTPS endpoint set
 	mustUpdate(t, fc, "operator-ns", opts.secretName, func(secret *corev1.Secret) {
@@ -243,7 +243,7 @@ func TestTailscaleIngressHostname(t *testing.T) {
 	expectReconciled(t, ingR, "default", "test")
 	ing.Finalizers = append(ing.Finalizers, "tailscale.com/finalizer")
 
-	expectEqual(t, fc, ing, nil)
+	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) {
@@ -259,7 +259,7 @@ func TestTailscaleIngressHostname(t *testing.T) {
 			{Hostname: "foo.tailnetxyz.ts.net", Ports: []networkingv1.IngressPortStatus{{Port: 443, Protocol: "TCP"}}},
 		},
 	}
-	expectEqual(t, fc, ing, nil)
+	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) {
@@ -271,7 +271,7 @@ func TestTailscaleIngressHostname(t *testing.T) {
 	})
 	expectReconciled(t, ingR, "default", "test")
 	ing.Status.LoadBalancer.Ingress = nil
-	expectEqual(t, fc, ing, 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) {
@@ -287,7 +287,7 @@ func TestTailscaleIngressHostname(t *testing.T) {
 		},
 	}
 	expectReconciled(t, ingR, "default", "test")
-	expectEqual(t, fc, ing, nil)
+	expectEqual(t, fc, ing)
 }
 
 func TestTailscaleIngressWithProxyClass(t *testing.T) {
@@ -295,7 +295,7 @@ func TestTailscaleIngressWithProxyClass(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"}}}},
 	}
@@ -383,9 +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.
@@ -393,7 +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
@@ -408,7 +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
@@ -418,18 +418,13 @@ 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{
-			Metrics: &tsapi.Metrics{
-				Enable:         true,
-				ServiceMonitor: &tsapi.ServiceMonitor{Enable: true},
-			},
-		},
+		Spec:       tsapi.ProxyClassSpec{},
 		Status: tsapi.ProxyClassStatus{
 			Conditions: []metav1.Condition{{
 				Status:             metav1.ConditionTrue,
@@ -437,32 +432,6 @@ func TestTailscaleIngressWithServiceMonitor(t *testing.T) {
 				ObservedGeneration: 1,
 			}}},
 	}
-	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).
-		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(),
-	}
-	// 1. Enable metrics- expect metrics Service to be created
 	ing := &networkingv1.Ingress{
 		TypeMeta: metav1.TypeMeta{Kind: "Ingress", APIVersion: "networking.k8s.io/v1"},
 		ObjectMeta: metav1.ObjectMeta{
@@ -491,8 +460,7 @@ func TestTailscaleIngressWithServiceMonitor(t *testing.T) {
 			},
 		},
 	}
-	mustCreate(t, fc, ing)
-	mustCreate(t, fc, &corev1.Service{
+	svc := &corev1.Service{
 		ObjectMeta: metav1.ObjectMeta{
 			Name:      "test",
 			Namespace: "default",
@@ -504,11 +472,38 @@ func TestTailscaleIngressWithServiceMonitor(t *testing.T) {
 				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{"${TS_CERT_DOMAIN}:443": {Handlers: map[string]*ipn.HTTPHandler{"/": {Proxy: "http://1.2.3.4:8080/"}}}},
+	}
 	opts := configOpts{
 		stsName:            shortName,
 		secretName:         fullName,
@@ -517,27 +512,51 @@ func TestTailscaleIngressWithServiceMonitor(t *testing.T) {
 		parentType:         "ingress",
 		hostname:           "default-test",
 		app:                kubetypes.AppIngressResource,
-		enableMetrics:      true,
 		namespaced:         true,
 		proxyType:          proxyTypeIngressResource,
+		serveConfig:        serveConfig,
+		resourceVersion:    "1",
 	}
-	serveConfig := &ipn.ServeConfig{
-		TCP: map[uint16]*ipn.TCPPortHandler{443: {HTTPS: true}},
-		Web: map[ipn.HostPort]*ipn.WebServerConfig{"${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), nil)
-	expectEqual(t, fc, expectedHeadlessService(shortName, "ingress"), nil)
-	expectEqual(t, fc, expectedMetricsService(opts), nil)
-	expectEqual(t, fc, expectedSTSUserspace(t, fc, opts), removeHashAnnotation)
+	// 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}
+		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

@@ -8,6 +8,7 @@ package main
 import (
 	"context"
 	"fmt"
+	"reflect"
 
 	"go.uber.org/zap"
 	corev1 "k8s.io/api/core/v1"
@@ -115,15 +116,15 @@ func reconcileMetricsResources(ctx context.Context, logger *zap.SugaredLogger, o
 		return maybeCleanupServiceMonitor(ctx, cl, opts.proxyStsName, opts.tsNamespace)
 	}
 
-	logger.Info("ensuring ServiceMonitor for metrics Service %s/%s", metricsSvc.Namespace, metricsSvc.Name)
-	svcMonitor, err := newServiceMonitor(metricsSvc)
+	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. We also do not update
-	// the ServiceMonitor because it is not expected that any of its fields would change. Currently this is good
-	// enough, but in future we might want to add logic to create-or-update unstructured types.
-	err = cl.Get(ctx, client.ObjectKeyFromObject(metricsSvc), svcMonitor.DeepCopy())
+
+	// 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)
@@ -133,6 +134,13 @@ func reconcileMetricsResources(ctx context.Context, logger *zap.SugaredLogger, o
 	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
 }
 
@@ -165,9 +173,13 @@ func maybeCleanupServiceMonitor(ctx context.Context, cl client.Client, stsName,
 // 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) (*unstructured.Unstructured, error) {
+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},
@@ -270,3 +282,14 @@ type metricsOpts struct {
 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_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

@@ -9,6 +9,7 @@ package main
 
 import (
 	"context"
+	"net/http"
 	"os"
 	"regexp"
 	"strconv"
@@ -18,7 +19,6 @@ import (
 	"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"
@@ -88,6 +88,15 @@ 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.
@@ -98,14 +107,14 @@ 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,
@@ -121,7 +130,7 @@ 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", "")
@@ -133,23 +142,10 @@ 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,
@@ -202,7 +198,7 @@ waitOnline:
 					},
 				},
 			}
-			authkey, _, err := tsClient.CreateKey(ctx, caps)
+			authkey, _, err := tsc.CreateKey(ctx, caps)
 			if err != nil {
 				startlog.Fatalf("creating operator authkey: %v", err)
 			}
@@ -226,7 +222,7 @@ waitOnline:
 		}
 		time.Sleep(time.Second)
 	}
-	return s, tsClient
+	return s, tsc
 }
 
 // runReconcilers starts the controller-runtime manager and registers the
@@ -320,6 +316,7 @@ 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).
@@ -341,6 +338,7 @@ 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).
@@ -360,6 +358,7 @@ 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).
@@ -433,12 +432,31 @@ func runReconcilers(opts reconcilerOpts) {
 		startlog.Fatalf("could not create egress EndpointSlices reconciler: %v", err)
 	}
 
+	podsForEps := handler.EnqueueRequestsFromMapFunc(podsFromEgressEps(mgr.GetClient(), opts.log, opts.tailscaleNamespace))
+	podsER := handler.EnqueueRequestsFromMapFunc(egressPodsHandler)
+	err = builder.
+		ControllerManagedBy(mgr).
+		Named("egress-pods-readiness-reconciler").
+		Watches(&discoveryv1.EndpointSlice{}, podsForEps).
+		Watches(&corev1.Pod{}, podsER).
+		Complete(&egressPodsReconciler{
+			Client:      mgr.GetClient(),
+			tsNamespace: opts.tailscaleNamespace,
+			clock:       tstime.DefaultClock{},
+			logger:      opts.log.Named("egress-pods-readiness-reconciler"),
+			httpClient:  http.DefaultClient,
+		})
+	if err != nil {
+		startlog.Fatalf("could not create egress Pods readiness 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(),
@@ -482,6 +500,7 @@ 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).
@@ -499,12 +518,14 @@ 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).
@@ -536,7 +557,7 @@ 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>
@@ -661,12 +682,6 @@ 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"
@@ -759,7 +774,7 @@ func proxyClassHandlerForConnector(cl client.Client, logger *zap.SugaredLogger)
 	}
 }
 
-// proxyClassHandlerForConnector returns a handler that, for a given ProxyClass,
+// proxyClassHandlerForProxyGroup returns a handler that, for a given ProxyClass,
 // returns a list of reconcile requests for all Connectors that have
 // .spec.proxyClass set.
 func proxyClassHandlerForProxyGroup(cl client.Client, logger *zap.SugaredLogger) handler.MapFunc {
@@ -802,6 +817,10 @@ 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)})
 			}
@@ -884,6 +903,20 @@ func egressEpsHandler(_ context.Context, o client.Object) []reconcile.Request {
 	}
 }
 
+func egressPodsHandler(_ context.Context, o client.Object) []reconcile.Request {
+	if typ := o.GetLabels()[LabelParentType]; typ != proxyTypeProxyGroup {
+		return nil
+	}
+	return []reconcile.Request{
+		{
+			NamespacedName: types.NamespacedName{
+				Namespace: o.GetNamespace(),
+				Name:      o.GetName(),
+			},
+		},
+	}
+}
+
 // egressEpsFromEgressPods returns a Pod event handler that checks if Pod is a replica for a ProxyGroup and if it is,
 // returns reconciler requests for all egress EndpointSlices for that ProxyGroup.
 func egressEpsFromPGPods(cl client.Client, ns string) handler.MapFunc {
@@ -976,7 +1009,7 @@ func reconcileRequestsForPG(pg string, cl client.Client, ns string) []reconcile.
 // egressSvcsFromEgressProxyGroup is an event handler for egress ProxyGroups. It returns reconcile requests for all
 // user-created ExternalName Services that should be exposed on this ProxyGroup.
 func egressSvcsFromEgressProxyGroup(cl client.Client, logger *zap.SugaredLogger) handler.MapFunc {
-	return func(_ context.Context, o client.Object) []reconcile.Request {
+	return func(ctx context.Context, o client.Object) []reconcile.Request {
 		pg, ok := o.(*tsapi.ProxyGroup)
 		if !ok {
 			logger.Infof("[unexpected] ProxyGroup handler triggered for an object that is not a ProxyGroup")
@@ -986,7 +1019,7 @@ func egressSvcsFromEgressProxyGroup(cl client.Client, logger *zap.SugaredLogger)
 			return nil
 		}
 		svcList := &corev1.ServiceList{}
-		if err := cl.List(context.Background(), svcList, client.MatchingFields{indexEgressProxyGroup: pg.Name}); err != nil {
+		if err := cl.List(ctx, svcList, client.MatchingFields{indexEgressProxyGroup: pg.Name}); err != nil {
 			logger.Infof("error listing Services: %v, skipping a reconcile for event on ProxyGroup %s", err, pg.Name)
 			return nil
 		}
@@ -1006,7 +1039,7 @@ func egressSvcsFromEgressProxyGroup(cl client.Client, logger *zap.SugaredLogger)
 // epsFromExternalNameService is an event handler for ExternalName Services that define a Tailscale egress service that
 // should be exposed on a ProxyGroup. It returns reconcile requests for EndpointSlices created for this Service.
 func epsFromExternalNameService(cl client.Client, logger *zap.SugaredLogger, ns string) handler.MapFunc {
-	return func(_ context.Context, o client.Object) []reconcile.Request {
+	return func(ctx context.Context, o client.Object) []reconcile.Request {
 		svc, ok := o.(*corev1.Service)
 		if !ok {
 			logger.Infof("[unexpected] Service handler triggered for an object that is not a Service")
@@ -1016,7 +1049,7 @@ func epsFromExternalNameService(cl client.Client, logger *zap.SugaredLogger, ns
 			return nil
 		}
 		epsList := &discoveryv1.EndpointSliceList{}
-		if err := cl.List(context.Background(), epsList, client.InNamespace(ns),
+		if err := cl.List(ctx, epsList, client.InNamespace(ns),
 			client.MatchingLabels(egressSvcChildResourceLabels(svc))); err != nil {
 			logger.Infof("error listing EndpointSlices: %v, skipping a reconcile for event on Service %s", err, svc.Name)
 			return nil
@@ -1034,6 +1067,43 @@ func epsFromExternalNameService(cl client.Client, logger *zap.SugaredLogger, ns
 	}
 }
 
+func podsFromEgressEps(cl client.Client, logger *zap.SugaredLogger, ns string) handler.MapFunc {
+	return func(ctx context.Context, o client.Object) []reconcile.Request {
+		eps, ok := o.(*discoveryv1.EndpointSlice)
+		if !ok {
+			logger.Infof("[unexpected] EndpointSlice handler triggered for an object that is not a EndpointSlice")
+			return nil
+		}
+		if eps.Labels[labelProxyGroup] == "" {
+			return nil
+		}
+		if eps.Labels[labelSvcType] != "egress" {
+			return nil
+		}
+		podLabels := map[string]string{
+			LabelManaged:    "true",
+			LabelParentType: "proxygroup",
+			LabelParentName: eps.Labels[labelProxyGroup],
+		}
+		podList := &corev1.PodList{}
+		if err := cl.List(ctx, podList, client.InNamespace(ns),
+			client.MatchingLabels(podLabels)); err != nil {
+			logger.Infof("error listing EndpointSlices: %v, skipping a reconcile for event on EndpointSlice %s", err, eps.Name)
+			return nil
+		}
+		reqs := make([]reconcile.Request, 0)
+		for _, pod := range podList.Items {
+			reqs = append(reqs, reconcile.Request{
+				NamespacedName: types.NamespacedName{
+					Namespace: pod.Namespace,
+					Name:      pod.Name,
+				},
+			})
+		}
+		return reqs
+	}
+}
+
 // 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 {
@@ -1085,3 +1155,8 @@ func indexEgressServices(o client.Object) []string {
 	}
 	return []string{o.GetAnnotations()[AnnotationProxyGroup]}
 }
+
+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) {
@@ -1336,73 +1336,9 @@ 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) {
-	fc := fake.NewFakeClient()
-	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,
-			defaultTags:       []string{"tag:k8s"},
-			operatorNamespace: "operator-ns",
-			proxyImage:        "tailscale/tailscale",
-		},
-		logger:                zl.Sugar(),
-		clock:                 clock,
-		isDefaultLoadBalancer: true,
-	}
-
-	// Create a service that we should manage, and check that the initial round
-	// of objects looks right.
-	mustCreate(t, fc, &corev1.Service{
-		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: corev1.ServiceSpec{
-			ClusterIP: "10.20.30.40",
-			Type:      corev1.ServiceTypeLoadBalancer,
-		},
-	})
-
-	expectReconciled(t, sr, "default", "test")
-
-	fullName, shortName := findGenName(t, fc, "default", "test", "svc")
-	o := configOpts{
-		stsName:         shortName,
-		secretName:      fullName,
-		namespace:       "default",
-		parentType:      "svc",
-		hostname:        "default-test",
-		clusterTargetIP: "10.20.30.40",
-		confFileHash:    "acf3467364b0a3ba9b8ee0dd772cb7c2f0bf585e288fa99b7fe4566009ed6041",
-		app:             kubetypes.AppIngressProxy,
-	}
-	expectEqual(t, fc, expectedSTS(t, fc, o), nil)
-
-	// 2. Hostname gets changed, configfile is updated and a new hash value
-	// is produced.
-	mustUpdate(t, fc, "default", "test", func(svc *corev1.Service) {
-		mak.Set(&svc.Annotations, AnnotationHostname, "another-test")
-	})
-	o.hostname = "another-test"
-	o.confFileHash = "d4cc13f09f55f4f6775689004f9a466723325b84d2b590692796bfe22aeaa389"
-	expectReconciled(t, sr, "default", "test")
-	expectEqual(t, fc, expectedSTS(t, fc, o), nil)
-}
 func Test_isMagicDNSName(t *testing.T) {
 	tests := []struct {
 		in   string
@@ -1679,9 +1615,9 @@ 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 +1629,7 @@ 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 +1689,9 @@ 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 +1699,107 @@ 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

@@ -115,7 +115,7 @@ func (pcr *ProxyClassReconciler) Reconcile(ctx context.Context, req reconcile.Re
 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...)
 			}
 		}
@@ -126,7 +126,7 @@ func (pcr *ProxyClassReconciler) validate(ctx context.Context, pc *tsapi.ProxyCl
 		}
 		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...)
 				}
 			}
@@ -178,6 +178,11 @@ func (pcr *ProxyClassReconciler) validate(ctx context.Context, pc *tsapi.ProxyCl
 			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

cmd/k8s-operator/proxyclass_test.go

@@ -36,10 +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"}},
@@ -78,7 +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"
@@ -88,7 +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})
 
@@ -102,7 +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})
 
@@ -121,7 +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})
 
@@ -145,7 +145,7 @@ func TestProxyClass(t *testing.T) {
 	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, nil)
+	expectEqual(t, fc, pc)
 	expectedEvent = "Warning ProxyClassInvalid " + msg
 	expectEvents(t, fr, []string{expectedEvent})
 
@@ -154,7 +154,26 @@ func TestProxyClass(t *testing.T) {
 	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, nil)
+	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) {

cmd/k8s-operator/proxygroup.go

@@ -32,6 +32,7 @@ import (
 	"tailscale.com/ipn"
 	tsoperator "tailscale.com/k8s-operator"
 	tsapi "tailscale.com/k8s-operator/apis/v1alpha1"
+	"tailscale.com/kube/egressservices"
 	"tailscale.com/kube/kubetypes"
 	"tailscale.com/tailcfg"
 	"tailscale.com/tstime"
@@ -51,7 +52,10 @@ const (
 	optimisticLockErrorMsg = "the object has been modified; please apply your changes to the latest version and try again"
 )
 
-var gaugeProxyGroupResources = clientmetric.NewGauge(kubetypes.MetricProxyGroupEgressCount)
+var (
+	gaugeEgressProxyGroupResources  = clientmetric.NewGauge(kubetypes.MetricProxyGroupEgressCount)
+	gaugeIngressProxyGroupResources = clientmetric.NewGauge(kubetypes.MetricProxyGroupIngressCount)
+)
 
 // ProxyGroupReconciler ensures cluster resources for a ProxyGroup definition.
 type ProxyGroupReconciler struct {
@@ -68,8 +72,9 @@ 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 {
@@ -162,6 +167,7 @@ func (r *ProxyGroupReconciler) Reconcile(ctx context.Context, req reconcile.Requ
 			r.recorder.Eventf(pg, corev1.EventTypeWarning, reasonProxyGroupCreationFailed, err.Error())
 			return setStatusReady(pg, metav1.ConditionFalse, reasonProxyGroupCreationFailed, err.Error())
 		}
+		validateProxyClassForPG(logger, pg, proxyClass)
 		if !tsoperator.ProxyClassIsReady(proxyClass) {
 			message := fmt.Sprintf("the ProxyGroup's ProxyClass %s is not yet in a ready state, waiting...", proxyClassName)
 			logger.Info(message)
@@ -200,11 +206,35 @@ func (r *ProxyGroupReconciler) Reconcile(ctx context.Context, req reconcile.Requ
 	return setStatusReady(pg, metav1.ConditionTrue, reasonProxyGroupReady, reasonProxyGroupReady)
 }
 
+// validateProxyClassForPG applies custom validation logic for ProxyClass applied to ProxyGroup.
+func validateProxyClassForPG(logger *zap.SugaredLogger, pg *tsapi.ProxyGroup, pc *tsapi.ProxyClass) {
+	if pg.Spec.Type == tsapi.ProxyGroupTypeIngress {
+		return
+	}
+	// Our custom logic for ensuring minimum downtime ProxyGroup update rollouts relies on the local health check
+	// beig accessible on the replica Pod IP:9002. This address can also be modified by users, via
+	// TS_LOCAL_ADDR_PORT env var.
+	//
+	// Currently TS_LOCAL_ADDR_PORT controls Pod's health check and metrics address. _Probably_ there is no need for
+	// users to set this to a custom value. Users who want to consume metrics, should integrate with the metrics
+	// Service and/or ServiceMonitor, rather than Pods directly. The health check is likely not useful to integrate
+	// directly with for operator proxies (and we should aim for unified lifecycle logic in the operator, users
+	// shouldn't need to set their own).
+	//
+	// TODO(irbekrm): maybe disallow configuring this env var in future (in Tailscale 1.84 or later).
+	if hasLocalAddrPortSet(pc) {
+		msg := fmt.Sprintf("ProxyClass %s applied to an egress ProxyGroup has TS_LOCAL_ADDR_PORT env var set to a custom value."+
+			"This will disable the ProxyGroup graceful failover mechanism, so you might experience downtime when ProxyGroup pods are restarted."+
+			"In future we will remove the ability to set custom TS_LOCAL_ADDR_PORT for egress ProxyGroups."+
+			"Please raise an issue if you expect that this will cause issues for your workflow.", pc.Name)
+		logger.Warn(msg)
+	}
+}
+
 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)
@@ -250,25 +280,62 @@ func (r *ProxyGroupReconciler) maybeProvision(ctx context.Context, pg *tsapi.Pro
 		return fmt.Errorf("error provisioning RoleBinding: %w", err)
 	}
 	if pg.Spec.Type == tsapi.ProxyGroupTypeEgress {
-		cm := pgEgressCM(pg, r.tsNamespace)
+		cm, hp := pgEgressCM(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
+			mak.Set(&existing.BinaryData, egressservices.KeyHEPPings, hp)
+		}); err != nil {
+			return fmt.Errorf("error provisioning egress ConfigMap %q: %w", cm.Name, err)
+		}
+	}
+	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 ConfigMap: %w", err)
+			return fmt.Errorf("error provisioning ingress ConfigMap %q: %w", cm.Name, err)
 		}
 	}
-	ss, err := pgStatefulSet(pg, r.tsNamespace, r.proxyImage, r.tsFirewallMode, cfgHash)
+	ss, err := pgStatefulSet(pg, r.tsNamespace, r.proxyImage, r.tsFirewallMode, proxyClass)
 	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{
@@ -358,8 +425,7 @@ func (r *ProxyGroupReconciler) maybeCleanup(ctx context.Context, pg *tsapi.Proxy
 
 	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
 }
@@ -469,6 +535,32 @@ func (r *ProxyGroupReconciler) ensureConfigSecretsCreated(ctx context.Context, p
 	return configSHA256Sum, 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) {
 	conf := &ipn.ConfigVAlpha{
 		Version:      "alpha0",
@@ -479,7 +571,7 @@ 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) {
@@ -536,12 +628,19 @@ 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
@@ -573,6 +672,29 @@ 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

@@ -7,11 +7,14 @@ package main
 
 import (
 	"fmt"
+	"slices"
+	"strconv"
 
 	appsv1 "k8s.io/api/apps/v1"
 	corev1 "k8s.io/api/core/v1"
 	rbacv1 "k8s.io/api/rbac/v1"
 	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
+	"k8s.io/apimachinery/pkg/util/intstr"
 	"sigs.k8s.io/yaml"
 	tsapi "tailscale.com/k8s-operator/apis/v1alpha1"
 	"tailscale.com/kube/egressservices"
@@ -19,9 +22,12 @@ import (
 	"tailscale.com/types/ptr"
 )
 
+// deletionGracePeriodSeconds is set to 6 minutes to ensure that the pre-stop hook of these proxies have enough chance to terminate gracefully.
+const deletionGracePeriodSeconds int64 = 360
+
 // 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, proxyClass *tsapi.ProxyClass) (*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)
@@ -53,12 +59,13 @@ 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) {
@@ -72,18 +79,16 @@ 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
 	}()
@@ -105,13 +110,11 @@ 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
 	}()
@@ -138,10 +141,6 @@ func pgStatefulSet(pg *tsapi.ProxyGroup, namespace, image, tsFirewallMode, cfgHa
 				Name:  "TS_EXPERIMENTAL_VERSIONED_CONFIG_DIR",
 				Value: "/etc/tsconfig/$(POD_NAME)",
 			},
-			{
-				Name:  "TS_INTERNAL_APP",
-				Value: kubetypes.AppProxyGroupEgress,
-			},
 		}
 
 		if tsFirewallMode != "" {
@@ -152,15 +151,57 @@ func pgStatefulSet(pg *tsapi.ProxyGroup, namespace, image, tsFirewallMode, cfgHa
 		}
 
 		if pg.Spec.Type == tsapi.ProxyGroupTypeEgress {
+			envs = append(envs,
+				// TODO(irbekrm): in 1.80 we deprecated TS_EGRESS_SERVICES_CONFIG_PATH in favour of
+				// TS_EGRESS_PROXIES_CONFIG_PATH. Remove it in 1.84.
+				corev1.EnvVar{
+					Name:  "TS_EGRESS_SERVICES_CONFIG_PATH",
+					Value: fmt.Sprintf("/etc/proxies/%s", egressservices.KeyEgressServices),
+				},
+				corev1.EnvVar{
+					Name:  "TS_EGRESS_PROXIES_CONFIG_PATH",
+					Value: "/etc/proxies",
+				},
+				corev1.EnvVar{
+					Name:  "TS_INTERNAL_APP",
+					Value: kubetypes.AppProxyGroupEgress,
+				},
+				corev1.EnvVar{
+					Name:  "TS_ENABLE_HEALTH_CHECK",
+					Value: "true",
+				})
+		} else { // ingress
 			envs = append(envs, corev1.EnvVar{
-				Name:  "TS_EGRESS_SERVICES_CONFIG_PATH",
-				Value: fmt.Sprintf("/etc/proxies/%s", egressservices.KeyEgressServices),
-			})
+				Name:  "TS_INTERNAL_APP",
+				Value: kubetypes.AppProxyGroupIngress,
+			},
+				corev1.EnvVar{
+					Name:  "TS_SERVE_CONFIG",
+					Value: fmt.Sprintf("/etc/proxies/%s", serveConfigKey),
+				})
 		}
-
 		return append(c.Env, envs...)
 	}()
 
+	// The pre-stop hook is used to ensure that a replica does not get terminated while cluster traffic for egress
+	// services is still being routed to it.
+	//
+	// This mechanism currently (2025-01-26) rely on the local health check being accessible on the Pod's
+	// IP, so they are not supported for ProxyGroups where users have configured TS_LOCAL_ADDR_PORT to a custom
+	// value.
+	if pg.Spec.Type == tsapi.ProxyGroupTypeEgress && !hasLocalAddrPortSet(proxyClass) {
+		c.Lifecycle = &corev1.Lifecycle{
+			PreStop: &corev1.LifecycleHandler{
+				HTTPGet: &corev1.HTTPGetAction{
+					Path: kubetypes.EgessServicesPreshutdownEP,
+					Port: intstr.FromInt(defaultLocalAddrPort),
+				},
+			},
+		}
+		// Set the deletion grace period to 6 minutes to ensure that the pre-stop hook has enough time to terminate
+		// gracefully.
+		ss.Spec.Template.DeletionGracePeriodSeconds = ptr.To(deletionGracePeriodSeconds)
+	}
 	return ss, nil
 }
 
@@ -252,7 +293,9 @@ func pgStateSecrets(pg *tsapi.ProxyGroup, namespace string) (secrets []*corev1.S
 	return secrets
 }
 
-func pgEgressCM(pg *tsapi.ProxyGroup, namespace string) *corev1.ConfigMap {
+func pgEgressCM(pg *tsapi.ProxyGroup, namespace string) (*corev1.ConfigMap, []byte) {
+	hp := hepPings(pg)
+	hpBs := []byte(strconv.Itoa(hp))
 	return &corev1.ConfigMap{
 		ObjectMeta: metav1.ObjectMeta{
 			Name:            pgEgressCMName(pg.Name),
@@ -260,6 +303,18 @@ func pgEgressCM(pg *tsapi.ProxyGroup, namespace string) *corev1.ConfigMap {
 			Labels:          pgLabels(pg.Name, nil),
 			OwnerReferences: pgOwnerReference(pg),
 		},
+		BinaryData: map[string][]byte{egressservices.KeyHEPPings: hpBs},
+	}, hpBs
+}
+
+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),
+		},
 	}
 }
 
@@ -297,3 +352,23 @@ func pgReplicas(pg *tsapi.ProxyGroup) int32 {
 func pgEgressCMName(pg string) string {
 	return fmt.Sprintf("%s-egress-config", pg)
 }
+
+// hasLocalAddrPortSet returns true if the proxyclass has the TS_LOCAL_ADDR_PORT env var set. For egress ProxyGroups,
+// currently (2025-01-26) this means that the ProxyGroup does not support graceful failover.
+func hasLocalAddrPortSet(proxyClass *tsapi.ProxyClass) bool {
+	if proxyClass == nil || proxyClass.Spec.StatefulSet == nil || proxyClass.Spec.StatefulSet.Pod == nil || proxyClass.Spec.StatefulSet.Pod.TailscaleContainer == nil {
+		return false
+	}
+	return slices.ContainsFunc(proxyClass.Spec.StatefulSet.Pod.TailscaleContainer.Env, func(env tsapi.Env) bool {
+		return env.Name == envVarTSLocalAddrPort
+	})
+}
+
+// hepPings returns the number of times a health check endpoint exposed by a Service fronting ProxyGroup replicas should
+// be pinged to ensure that all currently configured backend replicas are hit.
+func hepPings(pg *tsapi.ProxyGroup) int {
+	rc := pgReplicas(pg)
+	// Assuming a Service implemented using round robin load balancing, number-of-replica-times should be enough, but in
+	// practice, we cannot assume that the requests will be load balanced perfectly.
+	return int(rc) * 3
+}

cmd/k8s-operator/proxygroup_test.go

@@ -19,14 +19,17 @@ import (
 	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/apimachinery/pkg/util/intstr"
 	"k8s.io/client-go/tools/record"
 	"sigs.k8s.io/controller-runtime/pkg/client"
 	"sigs.k8s.io/controller-runtime/pkg/client/fake"
 	"tailscale.com/client/tailscale"
 	tsoperator "tailscale.com/k8s-operator"
 	tsapi "tailscale.com/k8s-operator/apis/v1alpha1"
+	"tailscale.com/kube/kubetypes"
 	"tailscale.com/tstest"
 	"tailscale.com/types/ptr"
+	"tailscale.com/util/mak"
 )
 
 const testProxyImage = "tailscale/tailscale:test"
@@ -53,6 +56,9 @@ func TestProxyGroup(t *testing.T) {
 			Name:       "test",
 			Finalizers: []string{"tailscale.com/finalizer"},
 		},
+		Spec: tsapi.ProxyGroupSpec{
+			Type: tsapi.ProxyGroupTypeEgress,
+		},
 	}
 
 	fc := fake.NewClientBuilder().
@@ -83,14 +89,15 @@ func TestProxyGroup(t *testing.T) {
 		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)
-		expectProxyGroupResources(t, fc, pg, false, "")
+		expectEqual(t, fc, pg)
+		expectProxyGroupResources(t, fc, pg, false, "", pc)
 	})
 
 	t.Run("observe_ProxyGroupCreating_status_reason", func(t *testing.T) {
@@ -110,12 +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)
-		expectProxyGroupResources(t, fc, pg, true, initialCfgHash)
-		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, "", pc)
+		if expected := 1; reconciler.egressProxyGroups.Len() != expected {
+			t.Fatalf("expected %d egress ProxyGroups, got %d", expected, reconciler.egressProxyGroups.Len())
 		}
-		expectProxyGroupResources(t, fc, pg, true, initialCfgHash)
+		expectProxyGroupResources(t, fc, pg, true, "", pc)
 		keyReq := tailscale.KeyCapabilities{
 			Devices: tailscale.KeyDeviceCapabilities{
 				Create: tailscale.KeyDeviceCreateCapabilities{
@@ -146,8 +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, initialCfgHash)
+		expectEqual(t, fc, pg)
+		expectProxyGroupResources(t, fc, pg, true, initialCfgHash, pc)
 	})
 
 	t.Run("scale_up_to_3", func(t *testing.T) {
@@ -157,8 +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)
-		expectProxyGroupResources(t, fc, pg, true, initialCfgHash)
+		expectEqual(t, fc, pg)
+		expectProxyGroupResources(t, fc, pg, true, initialCfgHash, pc)
 
 		addNodeIDToStateSecrets(t, fc, pg)
 		expectReconciled(t, reconciler, "", pg.Name)
@@ -167,8 +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, initialCfgHash)
+		expectEqual(t, fc, pg)
+		expectProxyGroupResources(t, fc, pg, true, initialCfgHash, pc)
 	})
 
 	t.Run("scale_down_to_1", func(t *testing.T) {
@@ -180,8 +187,8 @@ func TestProxyGroup(t *testing.T) {
 		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, initialCfgHash)
+		expectEqual(t, fc, pg)
+		expectProxyGroupResources(t, fc, pg, true, initialCfgHash, pc)
 	})
 
 	t.Run("trigger_config_change_and_observe_new_config_hash", func(t *testing.T) {
@@ -194,8 +201,8 @@ func TestProxyGroup(t *testing.T) {
 
 		expectReconciled(t, reconciler, "", pg.Name)
 
-		expectEqual(t, fc, pg, nil)
-		expectProxyGroupResources(t, fc, pg, true, "518a86e9fae64f270f8e0ec2a2ea6ca06c10f725035d3d6caca132cd61e42a74")
+		expectEqual(t, fc, pg)
+		expectProxyGroupResources(t, fc, pg, true, "518a86e9fae64f270f8e0ec2a2ea6ca06c10f725035d3d6caca132cd61e42a74", pc)
 	})
 
 	t.Run("enable_metrics", func(t *testing.T) {
@@ -204,7 +211,7 @@ func TestProxyGroup(t *testing.T) {
 			p.Spec = pc.Spec
 		})
 		expectReconciled(t, reconciler, "", pg.Name)
-		expectEqual(t, fc, expectedMetricsService(opts), nil)
+		expectEqual(t, fc, expectedMetricsService(opts))
 	})
 	t.Run("enable_service_monitor_no_crd", func(t *testing.T) {
 		pc.Spec.Metrics.ServiceMonitor = &tsapi.ServiceMonitor{Enable: true}
@@ -227,8 +234,8 @@ func TestProxyGroup(t *testing.T) {
 		expectReconciled(t, reconciler, "", pg.Name)
 
 		expectMissing[tsapi.ProxyGroup](t, fc, "", pg.Name)
-		if expected := 0; reconciler.proxyGroups.Len() != expected {
-			t.Fatalf("expected %d ProxyGroups, got %d", expected, reconciler.proxyGroups.Len())
+		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.
@@ -239,25 +246,249 @@ func TestProxyGroup(t *testing.T) {
 		// 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, cfgHash string) {
+func TestProxyGroupTypes(t *testing.T) {
+	pc := &tsapi.ProxyClass{
+		ObjectMeta: metav1.ObjectMeta{
+			Name:       "test",
+			Generation: 1,
+		},
+		Spec: tsapi.ProxyClassSpec{},
+	}
+	fc := fake.NewClientBuilder().
+		WithScheme(tsapi.GlobalScheme).
+		WithObjects(pc).
+		WithStatusSubresource(pc).
+		Build()
+	mustUpdateStatus(t, fc, "", pc.Name, func(p *tsapi.ProxyClass) {
+		p.Status.Conditions = []metav1.Condition{{
+			Type:               string(tsapi.ProxyClassReady),
+			Status:             metav1.ConditionTrue,
+			ObservedGeneration: 1,
+		}}
+	})
+
+	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),
+			},
+		}
+		mustCreate(t, fc, pg)
+
+		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_PROXIES_CONFIG_PATH", "/etc/proxies")
+		verifyEnvVar(t, sts, "TS_ENABLE_HEALTH_CHECK", "true")
+
+		// 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)
+		}
+
+		expectedLifecycle := corev1.Lifecycle{
+			PreStop: &corev1.LifecycleHandler{
+				HTTPGet: &corev1.HTTPGetAction{
+					Path: kubetypes.EgessServicesPreshutdownEP,
+					Port: intstr.FromInt(defaultLocalAddrPort),
+				},
+			},
+		}
+		if diff := cmp.Diff(expectedLifecycle, *sts.Spec.Template.Spec.Containers[0].Lifecycle); diff != "" {
+			t.Errorf("unexpected lifecycle (-want +got):\n%s", diff)
+		}
+		if *sts.Spec.Template.DeletionGracePeriodSeconds != deletionGracePeriodSeconds {
+			t.Errorf("unexpected deletion grace period seconds %d, want %d", *sts.Spec.Template.DeletionGracePeriodSeconds, deletionGracePeriodSeconds)
+		}
+	})
+	t.Run("egress_type_no_lifecycle_hook_when_local_addr_port_set", func(t *testing.T) {
+		pg := &tsapi.ProxyGroup{
+			ObjectMeta: metav1.ObjectMeta{
+				Name: "test-egress-no-lifecycle",
+				UID:  "test-egress-no-lifecycle-uid",
+			},
+			Spec: tsapi.ProxyGroupSpec{
+				Type:       tsapi.ProxyGroupTypeEgress,
+				Replicas:   ptr.To[int32](0),
+				ProxyClass: "test",
+			},
+		}
+		mustCreate(t, fc, pg)
+		mustUpdate(t, fc, "", pc.Name, func(p *tsapi.ProxyClass) {
+			p.Spec.StatefulSet = &tsapi.StatefulSet{
+				Pod: &tsapi.Pod{
+					TailscaleContainer: &tsapi.Container{
+						Env: []tsapi.Env{{
+							Name:  "TS_LOCAL_ADDR_PORT",
+							Value: "127.0.0.1:8080",
+						}},
+					},
+				},
+			}
+		})
+		expectReconciled(t, reconciler, "", pg.Name)
+
+		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)
+		}
+
+		if sts.Spec.Template.Spec.Containers[0].Lifecycle != nil {
+			t.Error("lifecycle hook was set when TS_LOCAL_ADDR_PORT was configured via ProxyClass")
+		}
+	})
+
+	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, 2)
+
+		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, proxyClass *tsapi.ProxyClass) {
 	t.Helper()
 
 	role := pgRole(pg, tsNamespace)
 	roleBinding := pgRoleBinding(pg, tsNamespace)
 	serviceAccount := pgServiceAccount(pg, tsNamespace)
-	statefulSet, err := pgStatefulSet(pg, tsNamespace, testProxyImage, "auto", cfgHash)
+	statefulSet, err := pgStatefulSet(pg, tsNamespace, testProxyImage, "auto", proxyClass)
 	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, nil)
+		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)

cmd/k8s-operator/sts.go

@@ -101,6 +101,9 @@ const (
 	proxyTypeIngressResource = "ingress_resource"
 	proxyTypeConnector       = "connector"
 	proxyTypeProxyGroup      = "proxygroup"
+
+	envVarTSLocalAddrPort = "TS_LOCAL_ADDR_PORT"
+	defaultLocalAddrPort  = 9002 // metrics and health check port
 )
 
 var (
@@ -172,8 +175,8 @@ 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
@@ -437,10 +440,10 @@ 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.
+// 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 {
@@ -449,12 +452,14 @@ func (a *tailscaleSTSReconciler) DeviceInfo(ctx context.Context, childLabels map
 	if sec == nil {
 		return dev, nil
 	}
+	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, nil
+		return dev, err
+	} else if err == nil {
+		podUID = string(pod.ObjectMeta.UID)
 	}
-
-	return deviceInfo(sec, pod, logger)
+	return deviceInfo(sec, podUID, logger)
 }
 
 // device contains tailscale state of a proxy device as gathered from its tailscale state Secret.
@@ -465,9 +470,10 @@ type device struct {
 	// 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, pod *corev1.Pod, log *zap.SugaredLogger) (dev *device, err error) {
+func deviceInfo(sec *corev1.Secret, podUID string, log *zap.SugaredLogger) (dev *device, err error) {
 	id := tailcfg.StableNodeID(sec.Data[kubetypes.KeyDeviceID])
 	if id == "" {
 		return dev, nil
@@ -484,10 +490,12 @@ func deviceInfo(sec *corev1.Secret, pod *corev1.Pod, log *zap.SugaredLogger) (de
 		// operator to clean up such devices.
 		return dev, nil
 	}
+	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.
-	dev.ingressDNSName = dev.hostname
-	if proxyCapVer(sec, pod, log) >= 109 {
+	if pcv >= 109 {
 		dev.ingressDNSName = strings.TrimSuffix(string(sec.Data[kubetypes.KeyHTTPSEndpoint]), ".")
 		if strings.EqualFold(dev.ingressDNSName, kubetypes.ValueNoHTTPS) {
 			dev.ingressDNSName = ""
@@ -584,8 +592,6 @@ 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",
@@ -655,6 +661,12 @@ 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
@@ -673,7 +685,25 @@ 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
 	}
@@ -761,7 +791,7 @@ 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 {
@@ -773,7 +803,7 @@ 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 {
@@ -1112,10 +1142,11 @@ func isValidFirewallMode(m string) bool {
 	return m == "auto" || m == "nftables" || m == "iptables"
 }
 
-// proxyCapVer accepts a proxy state Secret and a proxy Pod returns the capability version of a proxy Pod.
-// This is best effort - if the capability version can not (currently) be determined, it returns -1.
-func proxyCapVer(sec *corev1.Secret, pod *corev1.Pod, log *zap.SugaredLogger) tailcfg.CapabilityVersion {
-	if sec == nil || pod == nil {
+// 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 {
@@ -1126,7 +1157,7 @@ func proxyCapVer(sec *corev1.Secret, pod *corev1.Pod, log *zap.SugaredLogger) ta
 		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(string(pod.ObjectMeta.UID), string(sec.Data[kubetypes.KeyPodUID])) {
+	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)),
@@ -116,10 +116,10 @@ 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"},
 				},
 			},
@@ -146,7 +146,6 @@ func Test_applyProxyClassToStatefulSet(t *testing.T) {
 			},
 		}
 	}
-
 	var userspaceProxySS, nonUserspaceProxySS appsv1.StatefulSet
 	if err := yaml.Unmarshal(userspaceProxyYaml, &userspaceProxySS); err != nil {
 		t.Fatalf("unmarshaling userspace proxy template: %v", err)
@@ -176,9 +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
@@ -207,9 +206,9 @@ func Test_applyProxyClassToStatefulSet(t *testing.T) {
 	// 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 != "" {
@@ -219,9 +218,9 @@ func Test_applyProxyClassToStatefulSet(t *testing.T) {
 	// 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
@@ -243,9 +242,9 @@ func Test_applyProxyClassToStatefulSet(t *testing.T) {
 	// 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 != "" {
@@ -294,13 +293,6 @@ func Test_applyProxyClassToStatefulSet(t *testing.T) {
 	}
 }
 
-func mergeMapKeys(a, b map[string]string) map[string]string {
-	for key, val := range b {
-		a[key] = val
-	}
-	return a
-}
-
 func Test_mergeStatefulSetLabelsOrAnnots(t *testing.T) {
 	tests := []struct {
 		name    string
@@ -392,3 +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/testutils_test.go

@@ -9,6 +9,7 @@ import (
 	"context"
 	"encoding/json"
 	"fmt"
+	"net/http"
 	"net/netip"
 	"reflect"
 	"strings"
@@ -29,6 +30,7 @@ import (
 	"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"
@@ -61,7 +63,10 @@ type configOpts struct {
 	app                                            string
 	shouldRemoveAuthKey                            bool
 	secretExtraData                                map[string][]byte
-	enableMetrics                                  bool
+	resourceVersion                                string
+
+	enableMetrics        bool
+	serviceMonitorLabels tsapi.Labels
 }
 
 func expectedSTS(t *testing.T, cl client.Client, opts configOpts) *appsv1.StatefulSet {
@@ -92,7 +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{
 		{
@@ -110,7 +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{
@@ -119,13 +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,
@@ -136,13 +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{
@@ -431,14 +436,17 @@ func metricsLabels(opts configOpts) map[string]string {
 
 func expectedServiceMonitor(t *testing.T, opts configOpts) *unstructured.Unstructured {
 	t.Helper()
-	labels := metricsLabels(opts)
+	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:          labels,
-			ResourceVersion: "1",
+			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{
@@ -446,7 +454,7 @@ func expectedServiceMonitor(t *testing.T, opts configOpts) *unstructured.Unstruc
 			APIVersion: "monitoring.coreos.com/v1",
 		},
 		Spec: ServiceMonitorSpec{
-			Selector: metav1.LabelSelector{MatchLabels: labels},
+			Selector: metav1.LabelSelector{MatchLabels: metricsLabels(opts)},
 			Endpoints: []ServiceMonitorEndpoint{{
 				Port: "metrics",
 			}},
@@ -575,6 +583,21 @@ func mustCreate(t *testing.T, client client.Client, obj client.Object) {
 		t.Fatalf("creating %q: %v", obj.GetName(), err)
 	}
 }
+func mustCreateAll(t *testing.T, client client.Client, objs ...client.Object) {
+	t.Helper()
+	for _, obj := range objs {
+		mustCreate(t, client, obj)
+	}
+}
+
+func mustDeleteAll(t *testing.T, client client.Client, objs ...client.Object) {
+	t.Helper()
+	for _, obj := range objs {
+		if err := client.Delete(context.Background(), obj); err != nil {
+			t.Fatalf("deleting %q: %v", obj.GetName(), err)
+		}
+	}
+}
 
 func mustUpdate[T any, O ptrObject[T]](t *testing.T, client client.Client, ns, name string, update func(O)) {
 	t.Helper()
@@ -612,7 +635,7 @@ 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{
@@ -626,7 +649,7 @@ 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)
 	}
@@ -653,10 +676,11 @@ func expectEqualUnstructured(t *testing.T, client client.Client, want *unstructu
 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)
 	}
 }
@@ -697,6 +721,19 @@ func expectRequeue(t *testing.T, sr reconcile.Reconciler, ns, name string) {
 		t.Fatalf("expected timed requeue, got success")
 	}
 }
+func expectError(t *testing.T, sr reconcile.Reconciler, ns, name string) {
+	t.Helper()
+	req := reconcile.Request{
+		NamespacedName: types.NamespacedName{
+			Name:      name,
+			Namespace: ns,
+		},
+	}
+	_, err := sr.Reconcile(context.Background(), req)
+	if err == nil {
+		t.Error("Reconcile: expected error but did not get one")
+	}
+}
 
 // expectEvents accepts a test recorder and a list of events, tests that expected
 // events are sent down the recorder's channel. Waits for 5s for each event.
@@ -730,6 +767,7 @@ type fakeTSClient struct {
 	sync.Mutex
 	keyRequests []tailscale.KeyCapabilities
 	deleted     []string
+	vipServices map[string]*VIPService
 }
 type fakeTSNetServer struct {
 	certDomains []string
@@ -787,6 +825,15 @@ 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) {
@@ -826,3 +873,50 @@ func removeAuthKeyIfExistsModifier(t *testing.T) func(s *corev1.Secret) {
 		}
 	}
 }
+
+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_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/natc/natc.go

@@ -10,6 +10,7 @@ import (
 	"context"
 	"encoding/binary"
 	"errors"
+	"expvar"
 	"flag"
 	"fmt"
 	"log"
@@ -26,6 +27,8 @@ import (
 	"github.com/inetaf/tcpproxy"
 	"github.com/peterbourgon/ff/v3"
 	"golang.org/x/net/dns/dnsmessage"
+	"gvisor.dev/gvisor/pkg/tcpip"
+	"gvisor.dev/gvisor/pkg/tcpip/transport/tcp"
 	"tailscale.com/client/tailscale"
 	"tailscale.com/envknob"
 	"tailscale.com/hostinfo"
@@ -37,6 +40,7 @@ import (
 	"tailscale.com/tsweb"
 	"tailscale.com/util/dnsname"
 	"tailscale.com/util/mak"
+	"tailscale.com/wgengine/netstack"
 )
 
 func main() {
@@ -112,6 +116,7 @@ func main() {
 		ts.Port = uint16(*wgPort)
 	}
 	defer ts.Close()
+
 	if *verboseTSNet {
 		ts.Logf = log.Printf
 	}
@@ -129,6 +134,36 @@ func main() {
 			log.Fatalf("debug serve: %v", http.Serve(dln, mux))
 		}()
 	}
+
+	if err := ts.Start(); err != nil {
+		log.Fatalf("ts.Start: %v", err)
+	}
+	// TODO(raggi): this is not a public interface or guarantee.
+	ns := ts.Sys().Netstack.Get().(*netstack.Impl)
+	tcpRXBufOpt := tcpip.TCPReceiveBufferSizeRangeOption{
+		Min:     tcp.MinBufferSize,
+		Default: tcp.DefaultReceiveBufferSize,
+		Max:     tcp.MaxBufferSize,
+	}
+	if err := ns.SetTransportProtocolOption(tcp.ProtocolNumber, &tcpRXBufOpt); err != nil {
+		log.Fatalf("could not set TCP RX buf size: %v", err)
+	}
+	tcpTXBufOpt := tcpip.TCPSendBufferSizeRangeOption{
+		Min:     tcp.MinBufferSize,
+		Default: tcp.DefaultSendBufferSize,
+		Max:     tcp.MaxBufferSize,
+	}
+	if err := ns.SetTransportProtocolOption(tcp.ProtocolNumber, &tcpTXBufOpt); err != nil {
+		log.Fatalf("could not set TCP TX buf size: %v", err)
+	}
+	mslOpt := tcpip.TCPTimeWaitTimeoutOption(5 * time.Second)
+	if err := ns.SetTransportProtocolOption(tcp.ProtocolNumber, &mslOpt); err != nil {
+		log.Fatalf("could not set TCP MSL: %v", err)
+	}
+	if *debugPort != 0 {
+		expvar.Publish("netstack", ns.ExpVar())
+	}
+
 	lc, err := ts.LocalClient()
 	if err != nil {
 		log.Fatalf("LocalClient() failed: %v", err)

cmd/stund/depaware.txt

@@ -8,11 +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/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
@@ -55,6 +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
@@ -74,6 +75,7 @@ tailscale.com/cmd/stund dependencies: (generated by github.com/tailscale/depawar
    L 💣 tailscale.com/util/dirwalk                                   from tailscale.com/metrics
         tailscale.com/util/dnsname                                   from tailscale.com/tailcfg
         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
@@ -87,6 +89,8 @@ tailscale.com/cmd/stund dependencies: (generated by github.com/tailscale/depawar
         golang.org/x/crypto/cryptobyte/asn1                          from crypto/ecdsa+
         golang.org/x/crypto/curve25519                               from golang.org/x/crypto/nacl/box+
         golang.org/x/crypto/hkdf                                     from crypto/tls+
+        golang.org/x/crypto/internal/alias                           from golang.org/x/crypto/chacha20+
+        golang.org/x/crypto/internal/poly1305                        from golang.org/x/crypto/chacha20poly1305+
         golang.org/x/crypto/nacl/box                                 from tailscale.com/types/key
         golang.org/x/crypto/nacl/secretbox                           from golang.org/x/crypto/nacl/box
         golang.org/x/crypto/salsa20/salsa                            from golang.org/x/crypto/nacl/box+
@@ -121,6 +125,18 @@ tailscale.com/cmd/stund dependencies: (generated by github.com/tailscale/depawar
         crypto/ed25519                                               from crypto/tls+
         crypto/elliptic                                              from crypto/ecdsa+
         crypto/hmac                                                  from crypto/tls+
+        crypto/internal/alias                                        from crypto/aes+
+        crypto/internal/bigmod                                       from crypto/ecdsa+
+        crypto/internal/boring                                       from crypto/aes+
+        crypto/internal/boring/bbig                                  from crypto/ecdsa+
+        crypto/internal/boring/sig                                   from crypto/internal/boring
+        crypto/internal/edwards25519                                 from crypto/ed25519
+        crypto/internal/edwards25519/field                           from crypto/ecdh+
+        crypto/internal/hpke                                         from crypto/tls
+        crypto/internal/mlkem768                                     from crypto/tls
+        crypto/internal/nistec                                       from crypto/ecdh+
+        crypto/internal/nistec/fiat                                  from crypto/internal/nistec
+        crypto/internal/randutil                                     from crypto/dsa+
         crypto/md5                                                   from crypto/tls+
         crypto/rand                                                  from crypto/ed25519+
         crypto/rc4                                                   from crypto/tls
@@ -131,6 +147,7 @@ tailscale.com/cmd/stund dependencies: (generated by github.com/tailscale/depawar
         crypto/subtle                                                from crypto/aes+
         crypto/tls                                                   from net/http+
         crypto/x509                                                  from crypto/tls
+   D    crypto/x509/internal/macos                                   from crypto/x509
         crypto/x509/pkix                                             from crypto/x509
         embed                                                        from crypto/internal/nistec+
         encoding                                                     from encoding/json+
@@ -151,9 +168,46 @@ tailscale.com/cmd/stund dependencies: (generated by github.com/tailscale/depawar
         hash/fnv                                                     from google.golang.org/protobuf/internal/detrand
         hash/maphash                                                 from go4.org/mem
         html                                                         from net/http/pprof+
+        internal/abi                                                 from crypto/x509/internal/macos+
+        internal/asan                                                from syscall
+        internal/bisect                                              from internal/godebug
+        internal/bytealg                                             from bytes+
+        internal/byteorder                                           from crypto/aes+
+        internal/chacha8rand                                         from math/rand/v2+
+        internal/concurrent                                          from unique
+        internal/coverage/rtcov                                      from runtime
+        internal/cpu                                                 from crypto/aes+
+        internal/filepathlite                                        from os+
+        internal/fmtsort                                             from fmt
+        internal/goarch                                              from crypto/aes+
+        internal/godebug                                             from crypto/tls+
+        internal/godebugs                                            from internal/godebug+
+        internal/goexperiment                                        from runtime
+        internal/goos                                                from crypto/x509+
+        internal/itoa                                                from internal/poll+
+        internal/msan                                                from syscall
+        internal/nettrace                                            from net+
+        internal/oserror                                             from io/fs+
+        internal/poll                                                from net+
+        internal/profile                                             from net/http/pprof
+        internal/profilerecord                                       from runtime+
+        internal/race                                                from internal/poll+
+        internal/reflectlite                                         from context+
+        internal/runtime/atomic                                      from internal/runtime/exithook+
+        internal/runtime/exithook                                    from runtime
+   L    internal/runtime/syscall                                     from runtime+
+        internal/singleflight                                        from net
+        internal/stringslite                                         from embed+
+        internal/syscall/execenv                                     from os
+  LD    internal/syscall/unix                                        from crypto/rand+
+   W    internal/syscall/windows                                     from crypto/rand+
+   W    internal/syscall/windows/registry                            from mime+
+   W    internal/syscall/windows/sysdll                              from internal/syscall/windows+
+        internal/testlog                                             from os
+        internal/unsafeheader                                        from internal/reflectlite+
+        internal/weak                                                from unique
         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
@@ -170,6 +224,7 @@ tailscale.com/cmd/stund dependencies: (generated by github.com/tailscale/depawar
         net/http                                                     from expvar+
         net/http/httptrace                                           from net/http
         net/http/internal                                            from net/http
+        net/http/internal/ascii                                      from net/http
         net/http/pprof                                               from tailscale.com/tsweb
         net/netip                                                    from go4.org/netipx+
         net/textproto                                                from golang.org/x/net/http/httpguts+
@@ -181,7 +236,10 @@ tailscale.com/cmd/stund dependencies: (generated by github.com/tailscale/depawar
         reflect                                                      from crypto/x509+
         regexp                                                       from github.com/prometheus/client_golang/prometheus/internal+
         regexp/syntax                                                from regexp
+        runtime                                                      from crypto/internal/nistec+
         runtime/debug                                                from github.com/prometheus/client_golang/prometheus+
+        runtime/internal/math                                        from runtime
+        runtime/internal/sys                                         from runtime
         runtime/metrics                                              from github.com/prometheus/client_golang/prometheus+
         runtime/pprof                                                from net/http/pprof
         runtime/trace                                                from net/http/pprof
@@ -198,3 +256,4 @@ tailscale.com/cmd/stund dependencies: (generated by github.com/tailscale/depawar
         unicode/utf16                                                from crypto/x509+
         unicode/utf8                                                 from bufio+
         unique                                                       from net/netip
+        unsafe                                                       from bytes+

cmd/systray/logo.go

@@ -1,220 +0,0 @@
-// Copyright (c) Tailscale Inc & AUTHORS
-// SPDX-License-Identifier: BSD-3-Clause
-
-//go:build cgo || !darwin
-
-package main
-
-import (
-	"bytes"
-	"context"
-	"image/color"
-	"image/png"
-	"sync"
-	"time"
-
-	"fyne.io/systray"
-	"github.com/fogleman/gg"
-)
-
-// tsLogo represents the state of the 3x3 dot grid in the Tailscale logo.
-// A 0 represents a gray dot, any other value is a white dot.
-type tsLogo [9]byte
-
-var (
-	// disconnected is all gray dots
-	disconnected = tsLogo{
-		0, 0, 0,
-		0, 0, 0,
-		0, 0, 0,
-	}
-
-	// connected is the normal Tailscale logo
-	connected = tsLogo{
-		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{'l', 'o', 'a', 'd', 'i', 'n', 'g'}
-
-	// loadingIcons are shown in sequence as an animated loading icon.
-	loadingLogos = []tsLogo{
-		{
-			0, 1, 1,
-			1, 0, 1,
-			0, 0, 1,
-		},
-		{
-			0, 1, 1,
-			0, 0, 1,
-			0, 1, 0,
-		},
-		{
-			0, 1, 1,
-			0, 0, 0,
-			0, 0, 1,
-		},
-		{
-			0, 0, 1,
-			0, 1, 0,
-			0, 0, 0,
-		},
-		{
-			0, 1, 0,
-			0, 0, 0,
-			0, 0, 0,
-		},
-		{
-			0, 0, 0,
-			0, 0, 1,
-			0, 0, 0,
-		},
-		{
-			0, 0, 0,
-			0, 0, 0,
-			0, 0, 0,
-		},
-		{
-			0, 0, 1,
-			0, 0, 0,
-			0, 0, 0,
-		},
-		{
-			0, 0, 0,
-			0, 0, 0,
-			1, 0, 0,
-		},
-		{
-			0, 0, 0,
-			0, 0, 0,
-			1, 1, 0,
-		},
-		{
-			0, 0, 0,
-			1, 0, 0,
-			1, 1, 0,
-		},
-		{
-			0, 0, 0,
-			1, 1, 0,
-			0, 1, 0,
-		},
-		{
-			0, 0, 0,
-			1, 1, 0,
-			0, 1, 1,
-		},
-		{
-			0, 0, 0,
-			1, 1, 1,
-			0, 0, 1,
-		},
-		{
-			0, 1, 0,
-			0, 1, 1,
-			1, 0, 1,
-		},
-	}
-)
-
-var (
-	black = color.NRGBA{0, 0, 0, 255}
-	white = color.NRGBA{255, 255, 255, 255}
-	gray  = color.NRGBA{255, 255, 255, 102}
-)
-
-// render returns a PNG image of the logo.
-func (logo tsLogo) render() *bytes.Buffer {
-	const radius = 25
-	const borderUnits = 1
-	dim := radius * (8 + borderUnits*2)
-
-	dc := gg.NewContext(dim, dim)
-	dc.DrawRectangle(0, 0, float64(dim), float64(dim))
-	dc.SetColor(black)
-	dc.Fill()
-
-	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 := white
-			if logo[y*3+x] == 0 {
-				col = gray
-			}
-			dc.DrawCircle(float64(px), float64(py), radius)
-			dc.SetColor(col)
-			dc.Fill()
-		}
-	}
-
-	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 == loading {
-		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
-	}
-}

cmd/systray/systray.go

@@ -3,256 +3,13 @@
 
 //go:build cgo || !darwin
 
-// The systray command is a minimal Tailscale systray application for Linux.
+// systray is a minimal Tailscale systray application.
 package main
 
 import (
-	"context"
-	"errors"
-	"fmt"
-	"io"
-	"log"
-	"os"
-	"strings"
-	"sync"
-	"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"
-)
-
-var (
-	localClient tailscale.LocalClient
-	chState     chan ipn.State // tailscale state changes
-
-	appIcon *os.File
+	"tailscale.com/client/systray"
 )
 
 func main() {
-	systray.Run(onReady, onExit)
-}
-
-// Menu represents the systray menu, its items, and the current Tailscale state.
-type Menu struct {
-	mu     sync.Mutex // protects the entire Menu
-	status *ipnstate.Status
-
-	connect    *systray.MenuItem
-	disconnect *systray.MenuItem
-
-	self *systray.MenuItem
-	more *systray.MenuItem
-	quit *systray.MenuItem
-
-	eventCancel func() // cancel eventLoop
-}
-
-func onReady() {
-	log.Printf("starting")
-	ctx := context.Background()
-
-	setAppIcon(disconnected)
-
-	// dbus wants a file path for notification icons, so copy to a temp file.
-	appIcon, _ = os.CreateTemp("", "tailscale-systray.png")
-	io.Copy(appIcon, connected.render())
-
-	chState = make(chan ipn.State, 1)
-
-	status, err := localClient.Status(ctx)
-	if err != nil {
-		log.Print(err)
-	}
-
-	menu := new(Menu)
-	menu.rebuild(status)
-
-	go watchIPNBus(ctx)
-}
-
-// 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(status *ipnstate.Status) {
-	menu.mu.Lock()
-	defer menu.mu.Unlock()
-
-	if menu.eventCancel != nil {
-		menu.eventCancel()
-	}
-	menu.status = status
-	systray.ResetMenu()
-
-	menu.connect = systray.AddMenuItem("Connect", "")
-	menu.disconnect = systray.AddMenuItem("Disconnect", "")
-	menu.disconnect.Hide()
-	systray.AddSeparator()
-
-	if status != nil && status.Self != nil {
-		title := fmt.Sprintf("This Device: %s (%s)", status.Self.HostName, status.Self.TailscaleIPs[0])
-		menu.self = systray.AddMenuItem(title, "")
-	}
-	systray.AddSeparator()
-
-	menu.more = systray.AddMenuItem("More settings", "")
-	menu.more.Enable()
-
-	menu.quit = systray.AddMenuItem("Quit", "Quit the app")
-	menu.quit.Enable()
-
-	ctx := context.Background()
-	ctx, menu.eventCancel = context.WithCancel(ctx)
-	go menu.eventLoop(ctx)
-}
-
-// 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 state := <-chState:
-			switch state {
-			case ipn.Running:
-				setAppIcon(loading)
-				status, err := localClient.Status(ctx)
-				if err != nil {
-					log.Printf("error getting tailscale status: %v", err)
-				}
-				menu.rebuild(status)
-				setAppIcon(connected)
-				menu.connect.SetTitle("Connected")
-				menu.connect.Disable()
-				menu.disconnect.Show()
-				menu.disconnect.Enable()
-			case ipn.NoState, ipn.Stopped:
-				menu.connect.SetTitle("Connect")
-				menu.connect.Enable()
-				menu.disconnect.Hide()
-				setAppIcon(disconnected)
-			case ipn.Starting:
-				setAppIcon(loading)
-			}
-		case <-menu.connect.ClickedCh:
-			_, err := localClient.EditPrefs(ctx, &ipn.MaskedPrefs{
-				Prefs: ipn.Prefs{
-					WantRunning: true,
-				},
-				WantRunningSet: true,
-			})
-			if err != nil {
-				log.Print(err)
-				continue
-			}
-
-		case <-menu.disconnect.ClickedCh:
-			_, err := localClient.EditPrefs(ctx, &ipn.MaskedPrefs{
-				Prefs: ipn.Prefs{
-					WantRunning: false,
-				},
-				WantRunningSet: true,
-			})
-			if err != nil {
-				log.Printf("disconnecting: %v", err)
-				continue
-			}
-
-		case <-menu.self.ClickedCh:
-			copyTailscaleIP(menu.status.Self)
-
-		case <-menu.more.ClickedCh:
-			webbrowser.Open("http://100.100.100.100/")
-
-		case <-menu.quit.ClickedCh:
-			systray.Quit()
-		}
-	}
-}
-
-// watchIPNBus subscribes to the tailscale event bus and sends state updates to chState.
-// This method does not return.
-func watchIPNBus(ctx context.Context) {
-	for {
-		if err := watchIPNBusInner(ctx); 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 watchIPNBusInner(ctx context.Context) error {
-	watcher, err := localClient.WatchIPNBus(ctx, ipn.NotifyInitialState|ipn.NotifyNoPrivateKeys)
-	if err != nil {
-		return fmt.Errorf("watching ipn bus: %w", err)
-	}
-	defer watcher.Close()
-	for {
-		select {
-		case <-ctx.Done():
-			return nil
-		default:
-			n, err := watcher.Next()
-			if err != nil {
-				return fmt.Errorf("ipnbus error: %w", err)
-			}
-			if n.State != nil {
-				chState <- *n.State
-				log.Printf("new state: %v", n.State)
-			}
-		}
-	}
-}
-
-// copyTailscaleIP copies the first Tailscale IP of the given device to the clipboard
-// and sends a notification with the copied value.
-func 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)
-	}
-
-	sendNotification(fmt.Sprintf("Copied Address for %v", name), ip)
-}
-
-// sendNotification sends a desktop notification with the given title and content.
-func 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),
-		appIcon.Name(), title, content, []string{}, map[string]dbus.Variant{}, int32(timeout.Milliseconds()))
-	if call.Err != nil {
-		log.Printf("dbus: %v", call.Err)
-	}
-}
-
-func onExit() {
-	log.Printf("exiting")
-	os.Remove(appIcon.Name())
+	new(systray.Menu).Run()
 }

cmd/tailscale/cli/advertise.go

@@ -21,23 +21,21 @@ var advertiseArgs struct {
 
 // TODO(naman): This flag may move to set.go or serve_v2.go after the WIPCode
 // envknob is not needed.
-var advertiseCmd = &ffcli.Command{
-	Name:       "advertise",
-	ShortUsage: "tailscale advertise --services=<services>",
-	ShortHelp:  "Advertise this node as a destination for a service",
-	Exec:       runAdvertise,
-	FlagSet: (func() *flag.FlagSet {
-		fs := newFlagSet("advertise")
-		fs.StringVar(&advertiseArgs.services, "services", "", "comma-separated services to advertise; each must start with \"svc:\" (e.g. \"svc:idp,svc:nas,svc:database\")")
-		return fs
-	})(),
-}
-
-func maybeAdvertiseCmd() []*ffcli.Command {
+func advertiseCmd() *ffcli.Command {
 	if !envknob.UseWIPCode() {
 		return nil
 	}
-	return []*ffcli.Command{advertiseCmd}
+	return &ffcli.Command{
+		Name:       "advertise",
+		ShortUsage: "tailscale advertise --services=<services>",
+		ShortHelp:  "Advertise this node as a destination for a service",
+		Exec:       runAdvertise,
+		FlagSet: (func() *flag.FlagSet {
+			fs := newFlagSet("advertise")
+			fs.StringVar(&advertiseArgs.services, "services", "", "comma-separated services to advertise; each must start with \"svc:\" (e.g. \"svc:idp,svc:nas,svc:database\")")
+			return fs
+		})(),
+	}
 }
 
 func runAdvertise(ctx context.Context, args []string) error {
@@ -68,7 +66,7 @@ func parseServiceNames(servicesArg string) ([]string, error) {
 	if servicesArg != "" {
 		services = strings.Split(servicesArg, ",")
 		for _, svc := range services {
-			err := tailcfg.CheckServiceName(svc)
+			err := tailcfg.ServiceName(svc).Validate()
 			if err != nil {
 				return nil, fmt.Errorf("service %q: %s", svc, err)
 			}

cmd/tailscale/cli/cli.go

@@ -25,6 +25,7 @@ import (
 	"tailscale.com/cmd/tailscale/cli/ffcomplete"
 	"tailscale.com/envknob"
 	"tailscale.com/paths"
+	"tailscale.com/util/slicesx"
 	"tailscale.com/version/distro"
 )
 
@@ -84,9 +85,9 @@ var localClient = tailscale.LocalClient{
 
 // Run runs the CLI. The args do not include the binary name.
 func Run(args []string) (err error) {
-	if runtime.GOOS == "linux" && os.Getenv("GOKRAZY_FIRST_START") == "1" && distro.Get() == distro.Gokrazy && os.Getppid() == 1 {
-		// We're running on gokrazy and it's the first start.
-		// Don't run the tailscale CLI as a service; just exit.
+	if runtime.GOOS == "linux" && os.Getenv("GOKRAZY_FIRST_START") == "1" && distro.Get() == distro.Gokrazy && os.Getppid() == 1 && len(args) == 0 {
+		// We're running on gokrazy and the user did not specify 'up'.
+		// Don't run the tailscale CLI and spam logs with usage; just exit.
 		// See https://gokrazy.org/development/process-interface/
 		os.Exit(0)
 	}
@@ -182,14 +183,14 @@ For help on subcommands, add --help after: "tailscale status --help".
 This CLI is still under active development. Commands and flags will
 change in the future.
 `),
-		Subcommands: append([]*ffcli.Command{
+		Subcommands: nonNilCmds(
 			upCmd,
 			downCmd,
 			setCmd,
 			loginCmd,
 			logoutCmd,
 			switchCmd,
-			configureCmd,
+			configureCmd(),
 			syspolicyCmd,
 			netcheckCmd,
 			ipCmd,
@@ -211,10 +212,12 @@ change in the future.
 			exitNodeCmd(),
 			updateCmd,
 			whoisCmd,
-			debugCmd,
+			debugCmd(),
 			driveCmd,
 			idTokenCmd,
-		}, maybeAdvertiseCmd()...),
+			advertiseCmd(),
+			configureHostCmd(),
+		),
 		FlagSet: rootfs,
 		Exec: func(ctx context.Context, args []string) error {
 			if len(args) > 0 {
@@ -224,10 +227,6 @@ change in the future.
 		},
 	}
 
-	if runtime.GOOS == "linux" && distro.Get() == distro.Synology {
-		rootCmd.Subcommands = append(rootCmd.Subcommands, configureHostCmd)
-	}
-
 	walkCommands(rootCmd, func(w cmdWalk) bool {
 		if w.UsageFunc == nil {
 			w.UsageFunc = usageFunc
@@ -239,6 +238,10 @@ change in the future.
 	return rootCmd
 }
 
+func nonNilCmds(cmds ...*ffcli.Command) []*ffcli.Command {
+	return slicesx.AppendNonzero(cmds[:0], cmds)
+}
+
 func fatalf(format string, a ...any) {
 	if Fatalf != nil {
 		Fatalf(format, a...)

cmd/tailscale/cli/cli_test.go

@@ -17,6 +17,7 @@ import (
 
 	qt "github.com/frankban/quicktest"
 	"github.com/google/go-cmp/cmp"
+	"github.com/peterbourgon/ff/v3/ffcli"
 	"tailscale.com/envknob"
 	"tailscale.com/health/healthmsg"
 	"tailscale.com/ipn"
@@ -24,10 +25,12 @@ import (
 	"tailscale.com/tailcfg"
 	"tailscale.com/tka"
 	"tailscale.com/tstest"
+	"tailscale.com/tstest/deptest"
 	"tailscale.com/types/logger"
 	"tailscale.com/types/opt"
 	"tailscale.com/types/persist"
 	"tailscale.com/types/preftype"
+	"tailscale.com/util/set"
 	"tailscale.com/version/distro"
 )
 
@@ -601,6 +604,19 @@ func TestCheckForAccidentalSettingReverts(t *testing.T) {
 			goos: "linux",
 			want: "",
 		},
+		{
+			name:  "losing_posture_checking",
+			flags: []string{"--accept-dns"},
+			curPrefs: &ipn.Prefs{
+				ControlURL:          ipn.DefaultControlURL,
+				WantRunning:         false,
+				CorpDNS:             true,
+				PostureChecking:     true,
+				NetfilterMode:       preftype.NetfilterOn,
+				NoStatefulFiltering: opt.NewBool(true),
+			},
+			want: accidentalUpPrefix + " --accept-dns --posture-checking",
+		},
 	}
 	for _, tt := range tests {
 		t.Run(tt.name, func(t *testing.T) {
@@ -1045,6 +1061,7 @@ func TestUpdatePrefs(t *testing.T) {
 				NoSNATSet:                 true,
 				NoStatefulFilteringSet:    true,
 				OperatorUserSet:           true,
+				PostureCheckingSet:        true,
 				RouteAllSet:               true,
 				RunSSHSet:                 true,
 				ShieldsUpSet:              true,
@@ -1511,3 +1528,73 @@ func TestHelpAlias(t *testing.T) {
 		t.Fatalf("Run: %v", err)
 	}
 }
+
+func TestDocs(t *testing.T) {
+	root := newRootCmd()
+	check := func(t *testing.T, c *ffcli.Command) {
+		shortVerb, _, ok := strings.Cut(c.ShortHelp, " ")
+		if !ok || shortVerb == "" {
+			t.Errorf("couldn't find verb+space in ShortHelp")
+		} else {
+			if strings.HasSuffix(shortVerb, ".") {
+				t.Errorf("ShortHelp shouldn't end in period; got %q", c.ShortHelp)
+			}
+			if b := shortVerb[0]; b >= 'a' && b <= 'z' {
+				t.Errorf("ShortHelp should start with upper-case letter; got %q", c.ShortHelp)
+			}
+			if strings.HasSuffix(shortVerb, "s") && shortVerb != "Does" {
+				t.Errorf("verb %q ending in 's' is unexpected, from %q", shortVerb, c.ShortHelp)
+			}
+		}
+
+		name := t.Name()
+		wantPfx := strings.ReplaceAll(strings.TrimPrefix(name, "TestDocs/"), "/", " ")
+		switch name {
+		case "TestDocs/tailscale/completion/bash",
+			"TestDocs/tailscale/completion/zsh":
+			wantPfx = "" // special-case exceptions
+		}
+		if !strings.HasPrefix(c.ShortUsage, wantPfx) {
+			t.Errorf("ShortUsage should start with %q; got %q", wantPfx, c.ShortUsage)
+		}
+	}
+
+	var walk func(t *testing.T, c *ffcli.Command)
+	walk = func(t *testing.T, c *ffcli.Command) {
+		t.Run(c.Name, func(t *testing.T) {
+			check(t, c)
+			for _, sub := range c.Subcommands {
+				walk(t, sub)
+			}
+		})
+	}
+	walk(t, root)
+}
+
+func TestDeps(t *testing.T) {
+	deptest.DepChecker{
+		GOOS:   "linux",
+		GOARCH: "arm64",
+		WantDeps: set.Of(
+			"tailscale.com/feature/capture/dissector", // want the Lua by default
+		),
+		BadDeps: map[string]string{
+			"tailscale.com/feature/capture": "don't link capture code",
+			"tailscale.com/net/packet":      "why we passing packets in the CLI?",
+			"tailscale.com/net/flowtrack":   "why we tracking flows in the CLI?",
+		},
+	}.Check(t)
+}
+
+func TestDepsNoCapture(t *testing.T) {
+	deptest.DepChecker{
+		GOOS:   "linux",
+		GOARCH: "arm64",
+		Tags:   "ts_omit_capture",
+		BadDeps: map[string]string{
+			"tailscale.com/feature/capture":           "don't link capture code",
+			"tailscale.com/feature/capture/dissector": "don't like the Lua",
+		},
+	}.Check(t)
+
+}

cmd/tailscale/cli/configure-kube.go

@@ -20,33 +20,31 @@ import (
 	"tailscale.com/version"
 )
 
-func init() {
-	configureCmd.Subcommands = append(configureCmd.Subcommands, configureKubeconfigCmd)
-}
-
-var configureKubeconfigCmd = &ffcli.Command{
-	Name:       "kubeconfig",
-	ShortHelp:  "[ALPHA] Connect to a Kubernetes cluster using a Tailscale Auth Proxy",
-	ShortUsage: "tailscale configure kubeconfig <hostname-or-fqdn>",
-	LongHelp: strings.TrimSpace(`
+func configureKubeconfigCmd() *ffcli.Command {
+	return &ffcli.Command{
+		Name:       "kubeconfig",
+		ShortHelp:  "[ALPHA] Connect to a Kubernetes cluster using a Tailscale Auth Proxy",
+		ShortUsage: "tailscale configure kubeconfig <hostname-or-fqdn>",
+		LongHelp: strings.TrimSpace(`
 Run this command to configure kubectl to connect to a Kubernetes cluster over Tailscale.
 
 The hostname argument should be set to the Tailscale hostname of the peer running as an auth proxy in the cluster.
 
 See: https://tailscale.com/s/k8s-auth-proxy
 `),
-	FlagSet: (func() *flag.FlagSet {
-		fs := newFlagSet("kubeconfig")
-		return fs
-	})(),
-	Exec: runConfigureKubeconfig,
+		FlagSet: (func() *flag.FlagSet {
+			fs := newFlagSet("kubeconfig")
+			return fs
+		})(),
+		Exec: runConfigureKubeconfig,
+	}
 }
 
 // kubeconfigPath returns the path to the kubeconfig file for the current user.
 func kubeconfigPath() (string, error) {
 	if kubeconfig := os.Getenv("KUBECONFIG"); kubeconfig != "" {
 		if version.IsSandboxedMacOS() {
-			return "", errors.New("$KUBECONFIG is incompatible with the App Store version")
+			return "", errors.New("cannot read $KUBECONFIG on GUI builds of the macOS client: this requires the open-source tailscaled distribution")
 		}
 		var out string
 		for _, out = range filepath.SplitList(kubeconfig) {

cmd/tailscale/cli/configure-kube_omit.go

@@ -0,0 +1,13 @@
+// Copyright (c) Tailscale Inc & AUTHORS
+// SPDX-License-Identifier: BSD-3-Clause
+
+//go:build ts_omit_kube
+
+package cli
+
+import "github.com/peterbourgon/ff/v3/ffcli"
+
+func configureKubeconfigCmd() *ffcli.Command {
+	// omitted from the build when the ts_omit_kube build tag is set
+	return nil
+}

cmd/tailscale/cli/configure-synology-cert.go

@@ -22,22 +22,27 @@ import (
 	"tailscale.com/version/distro"
 )
 
-var synologyConfigureCertCmd = &ffcli.Command{
-	Name:       "synology-cert",
-	Exec:       runConfigureSynologyCert,
-	ShortHelp:  "Configure Synology with a TLS certificate for your tailnet",
-	ShortUsage: "synology-cert [--domain <domain>]",
-	LongHelp: strings.TrimSpace(`
+func synologyConfigureCertCmd() *ffcli.Command {
+	if runtime.GOOS != "linux" || distro.Get() != distro.Synology {
+		return nil
+	}
+	return &ffcli.Command{
+		Name:       "synology-cert",
+		Exec:       runConfigureSynologyCert,
+		ShortHelp:  "Configure Synology with a TLS certificate for your tailnet",
+		ShortUsage: "synology-cert [--domain <domain>]",
+		LongHelp: strings.TrimSpace(`
 This command is intended to run periodically as root on a Synology device to
 create or refresh the TLS certificate for the tailnet domain.
 
 See: https://tailscale.com/kb/1153/enabling-https
 `),
-	FlagSet: (func() *flag.FlagSet {
-		fs := newFlagSet("synology-cert")
-		fs.StringVar(&synologyConfigureCertArgs.domain, "domain", "", "Tailnet domain to create or refresh certificates for. Ignored if only one domain exists.")
-		return fs
-	})(),
+		FlagSet: (func() *flag.FlagSet {
+			fs := newFlagSet("synology-cert")
+			fs.StringVar(&synologyConfigureCertArgs.domain, "domain", "", "Tailnet domain to create or refresh certificates for. Ignored if only one domain exists.")
+			return fs
+		})(),
+	}
 }
 
 var synologyConfigureCertArgs struct {

cmd/tailscale/cli/configure-synology.go

@@ -21,34 +21,49 @@ import (
 // configureHostCmd is the "tailscale configure-host" command which was once
 // used to configure Synology devices, but is now a compatibility alias to
 // "tailscale configure synology".
-var configureHostCmd = &ffcli.Command{
-	Name:       "configure-host",
-	Exec:       runConfigureSynology,
-	ShortUsage: "tailscale configure-host\n" + synologyConfigureCmd.ShortUsage,
-	ShortHelp:  synologyConfigureCmd.ShortHelp,
-	LongHelp:   hidden + synologyConfigureCmd.LongHelp,
-	FlagSet: (func() *flag.FlagSet {
-		fs := newFlagSet("configure-host")
-		return fs
-	})(),
+//
+// It returns nil if the actual "tailscale configure synology" command is not
+// available.
+func configureHostCmd() *ffcli.Command {
+	synologyConfigureCmd := synologyConfigureCmd()
+	if synologyConfigureCmd == nil {
+		// No need to offer this compatibility alias if the actual command is not available.
+		return nil
+	}
+	return &ffcli.Command{
+		Name:       "configure-host",
+		Exec:       runConfigureSynology,
+		ShortUsage: "tailscale configure-host\n" + synologyConfigureCmd.ShortUsage,
+		ShortHelp:  synologyConfigureCmd.ShortHelp,
+		LongHelp:   hidden + synologyConfigureCmd.LongHelp,
+		FlagSet: (func() *flag.FlagSet {
+			fs := newFlagSet("configure-host")
+			return fs
+		})(),
+	}
 }
 
-var synologyConfigureCmd = &ffcli.Command{
-	Name:       "synology",
-	Exec:       runConfigureSynology,
-	ShortUsage: "tailscale configure synology",
-	ShortHelp:  "Configure Synology to enable outbound connections",
-	LongHelp: strings.TrimSpace(`
+func synologyConfigureCmd() *ffcli.Command {
+	if runtime.GOOS != "linux" || distro.Get() != distro.Synology {
+		return nil
+	}
+	return &ffcli.Command{
+		Name:       "synology",
+		Exec:       runConfigureSynology,
+		ShortUsage: "tailscale configure synology",
+		ShortHelp:  "Configure Synology to enable outbound connections",
+		LongHelp: strings.TrimSpace(`
 This command is intended to run at boot as root on a Synology device to
 create the /dev/net/tun device and give the tailscaled binary permission
 to use it.
 
 See: https://tailscale.com/s/synology-outbound
 `),
-	FlagSet: (func() *flag.FlagSet {
-		fs := newFlagSet("synology")
-		return fs
-	})(),
+		FlagSet: (func() *flag.FlagSet {
+			fs := newFlagSet("synology")
+			return fs
+		})(),
+	}
 }
 
 func runConfigureSynology(ctx context.Context, args []string) error {

cmd/tailscale/cli/configure.go

@@ -5,32 +5,41 @@ package cli
 
 import (
 	"flag"
-	"runtime"
 	"strings"
 
 	"github.com/peterbourgon/ff/v3/ffcli"
-	"tailscale.com/version/distro"
 )
 
-var configureCmd = &ffcli.Command{
-	Name:       "configure",
-	ShortUsage: "tailscale configure <subcommand>",
-	ShortHelp:  "[ALPHA] Configure the host to enable more Tailscale features",
-	LongHelp: strings.TrimSpace(`
+func configureCmd() *ffcli.Command {
+	return &ffcli.Command{
+		Name:       "configure",
+		ShortUsage: "tailscale configure <subcommand>",
+		ShortHelp:  "Configure the host to enable more Tailscale features",
+		LongHelp: strings.TrimSpace(`
 The 'configure' set of commands are intended to provide a way to enable different
 services on the host to use Tailscale in more ways.
 `),
-	FlagSet: (func() *flag.FlagSet {
-		fs := newFlagSet("configure")
-		return fs
-	})(),
-	Subcommands: configureSubcommands(),
+		FlagSet: (func() *flag.FlagSet {
+			fs := newFlagSet("configure")
+			return fs
+		})(),
+		Subcommands: nonNilCmds(
+			configureKubeconfigCmd(),
+			synologyConfigureCmd(),
+			synologyConfigureCertCmd(),
+			ccall(maybeSysExtCmd),
+			ccall(maybeVPNConfigCmd),
+		),
+	}
 }
 
-func configureSubcommands() (out []*ffcli.Command) {
-	if runtime.GOOS == "linux" && distro.Get() == distro.Synology {
-		out = append(out, synologyConfigureCmd)
-		out = append(out, synologyConfigureCertCmd)
+// ccall calls the function f if it is non-nil, and returns its result.
+//
+// It returns the zero value of the type T if f is nil.
+func ccall[T any](f func() T) T {
+	var zero T
+	if f == nil {
+		return zero
 	}
-	return out
+	return f()
 }

cmd/tailscale/cli/configure_apple-all.go

@@ -0,0 +1,11 @@
+// Copyright (c) Tailscale Inc & AUTHORS
+// SPDX-License-Identifier: BSD-3-Clause
+
+package cli
+
+import "github.com/peterbourgon/ff/v3/ffcli"
+
+var (
+	maybeSysExtCmd    func() *ffcli.Command // non-nil only on macOS, see configure_apple.go
+	maybeVPNConfigCmd func() *ffcli.Command // non-nil only on macOS, see configure_apple.go
+)

cmd/tailscale/cli/configure_apple.go

@@ -0,0 +1,97 @@
+// Copyright (c) Tailscale Inc & AUTHORS
+// SPDX-License-Identifier: BSD-3-Clause
+
+//go:build darwin
+
+package cli
+
+import (
+	"context"
+	"errors"
+
+	"github.com/peterbourgon/ff/v3/ffcli"
+)
+
+func init() {
+	maybeSysExtCmd = sysExtCmd
+	maybeVPNConfigCmd = vpnConfigCmd
+}
+
+// Functions in this file provide a dummy Exec function that only prints an error message for users of the open-source
+// tailscaled distribution. On GUI builds, the Swift code in the macOS client handles these commands by not passing the
+// flow of execution to the CLI.
+
+// sysExtCmd returns a command for managing the Tailscale system extension on macOS
+// (for the Standalone variant of the client only).
+func sysExtCmd() *ffcli.Command {
+	return &ffcli.Command{
+		Name:       "sysext",
+		ShortUsage: "tailscale configure sysext [activate|deactivate|status]",
+		ShortHelp:  "Manage the system extension for macOS (Standalone variant)",
+		LongHelp: "The sysext set of commands provides a way to activate, deactivate, or manage the state of the Tailscale system extension on macOS. " +
+			"This is only relevant if you are running the Standalone variant of the Tailscale client for macOS. " +
+			"To access more detailed information about system extensions installed on this Mac, run 'systemextensionsctl list'.",
+		Subcommands: []*ffcli.Command{
+			{
+				Name:       "activate",
+				ShortUsage: "tailscale configure sysext activate",
+				ShortHelp:  "Register the Tailscale system extension with macOS.",
+				LongHelp:   "This command registers the Tailscale system extension with macOS. To run Tailscale, you'll also need to install the VPN configuration separately (run `tailscale configure vpn-config install`). After running this command, you need to approve the extension in System Settings > Login Items and Extensions > Network Extensions.",
+				Exec:       requiresStandalone,
+			},
+			{
+				Name:       "deactivate",
+				ShortUsage: "tailscale configure sysext deactivate",
+				ShortHelp:  "Deactivate the Tailscale system extension on macOS",
+				LongHelp:   "This command deactivates the Tailscale system extension on macOS. To completely remove Tailscale, you'll also need to delete the VPN configuration separately (use `tailscale configure vpn-config uninstall`).",
+				Exec:       requiresStandalone,
+			},
+			{
+				Name:       "status",
+				ShortUsage: "tailscale configure sysext status",
+				ShortHelp:  "Print the enablement status of the Tailscale system extension",
+				LongHelp:   "This command prints the enablement status of the Tailscale system extension. If the extension is not enabled, run `tailscale sysext activate` to enable it.",
+				Exec:       requiresStandalone,
+			},
+		},
+		Exec: requiresStandalone,
+	}
+}
+
+// vpnConfigCmd returns a command for managing the Tailscale VPN configuration on macOS
+// (the entry that appears in System Settings > VPN).
+func vpnConfigCmd() *ffcli.Command {
+	return &ffcli.Command{
+		Name:       "mac-vpn",
+		ShortUsage: "tailscale configure mac-vpn [install|uninstall]",
+		ShortHelp:  "Manage the VPN configuration on macOS (App Store and Standalone variants)",
+		LongHelp:   "The vpn-config set of commands provides a way to add or remove the Tailscale VPN configuration from the macOS settings. This is the entry that appears in System Settings > VPN.",
+		Subcommands: []*ffcli.Command{
+			{
+				Name:       "install",
+				ShortUsage: "tailscale configure mac-vpn install",
+				ShortHelp:  "Write the Tailscale VPN configuration to the macOS settings",
+				LongHelp:   "This command writes the Tailscale VPN configuration to the macOS settings. This is the entry that appears in System Settings > VPN. If you are running the Standalone variant of the client, you'll also need to install the system extension separately (run `tailscale configure sysext activate`).",
+				Exec:       requiresGUI,
+			},
+			{
+				Name:       "uninstall",
+				ShortUsage: "tailscale configure mac-vpn uninstall",
+				ShortHelp:  "Delete the Tailscale VPN configuration from the macOS settings",
+				LongHelp:   "This command removes the Tailscale VPN configuration from the macOS settings. This is the entry that appears in System Settings > VPN. If you are running the Standalone variant of the client, you'll also need to deactivate the system extension separately (run `tailscale configure sysext deactivate`).",
+				Exec:       requiresGUI,
+			},
+		},
+		Exec: func(ctx context.Context, args []string) error {
+			return errors.New("unsupported command: requires a GUI build of the macOS client")
+		},
+	}
+}
+
+func requiresStandalone(ctx context.Context, args []string) error {
+	return errors.New("unsupported command: requires the Standalone (.pkg installer) GUI build of the client")
+}
+
+func requiresGUI(ctx context.Context, args []string) error {
+	return errors.New("unsupported command: requires a GUI build of the macOS client")
+}

cmd/tailscale/cli/debug-capture.go

@@ -0,0 +1,80 @@
+// Copyright (c) Tailscale Inc & AUTHORS
+// SPDX-License-Identifier: BSD-3-Clause
+
+//go:build !ios && !ts_omit_capture
+
+package cli
+
+import (
+	"context"
+	"flag"
+	"fmt"
+	"io"
+	"os"
+	"os/exec"
+
+	"github.com/peterbourgon/ff/v3/ffcli"
+	"tailscale.com/feature/capture/dissector"
+)
+
+func init() {
+	debugCaptureCmd = mkDebugCaptureCmd
+}
+
+func mkDebugCaptureCmd() *ffcli.Command {
+	return &ffcli.Command{
+		Name:       "capture",
+		ShortUsage: "tailscale debug capture",
+		Exec:       runCapture,
+		ShortHelp:  "Stream pcaps for debugging",
+		FlagSet: (func() *flag.FlagSet {
+			fs := newFlagSet("capture")
+			fs.StringVar(&captureArgs.outFile, "o", "", "path to stream the pcap (or - for stdout), leave empty to start wireshark")
+			return fs
+		})(),
+	}
+}
+
+var captureArgs struct {
+	outFile string
+}
+
+func runCapture(ctx context.Context, args []string) error {
+	stream, err := localClient.StreamDebugCapture(ctx)
+	if err != nil {
+		return err
+	}
+	defer stream.Close()
+
+	switch captureArgs.outFile {
+	case "-":
+		fmt.Fprintln(Stderr, "Press Ctrl-C to stop the capture.")
+		_, err = io.Copy(os.Stdout, stream)
+		return err
+	case "":
+		lua, err := os.CreateTemp("", "ts-dissector")
+		if err != nil {
+			return err
+		}
+		defer os.Remove(lua.Name())
+		io.WriteString(lua, dissector.Lua)
+		if err := lua.Close(); err != nil {
+			return err
+		}
+
+		wireshark := exec.CommandContext(ctx, "wireshark", "-X", "lua_script:"+lua.Name(), "-k", "-i", "-")
+		wireshark.Stdin = stream
+		wireshark.Stdout = os.Stdout
+		wireshark.Stderr = os.Stderr
+		return wireshark.Run()
+	}
+
+	f, err := os.OpenFile(captureArgs.outFile, os.O_WRONLY|os.O_CREATE|os.O_TRUNC, 0644)
+	if err != nil {
+		return err
+	}
+	defer f.Close()
+	fmt.Fprintln(Stderr, "Press Ctrl-C to stop the capture.")
+	_, err = io.Copy(f, stream)
+	return err
+}

cmd/tailscale/cli/debug.go

@@ -20,7 +20,6 @@ import (
 	"net/netip"
 	"net/url"
 	"os"
-	"os/exec"
 	"runtime"
 	"runtime/debug"
 	"strconv"
@@ -45,307 +44,302 @@ import (
 	"tailscale.com/types/key"
 	"tailscale.com/types/logger"
 	"tailscale.com/util/must"
-	"tailscale.com/wgengine/capture"
 )
 
-var debugCmd = &ffcli.Command{
-	Name:       "debug",
-	Exec:       runDebug,
-	ShortUsage: "tailscale debug <debug-flags | subcommand>",
-	ShortHelp:  "Debug commands",
-	LongHelp:   hidden + `"tailscale debug" contains misc debug facilities; it is not a stable interface.`,
-	FlagSet: (func() *flag.FlagSet {
-		fs := newFlagSet("debug")
-		fs.StringVar(&debugArgs.file, "file", "", "get, delete:NAME, or NAME")
-		fs.StringVar(&debugArgs.cpuFile, "cpu-profile", "", "if non-empty, grab a CPU profile for --profile-seconds seconds and write it to this file; - for stdout")
-		fs.StringVar(&debugArgs.memFile, "mem-profile", "", "if non-empty, grab a memory profile and write it to this file; - for stdout")
-		fs.IntVar(&debugArgs.cpuSec, "profile-seconds", 15, "number of seconds to run a CPU profile for, when --cpu-profile is non-empty")
-		return fs
-	})(),
-	Subcommands: []*ffcli.Command{
-		{
-			Name:       "derp-map",
-			ShortUsage: "tailscale debug derp-map",
-			Exec:       runDERPMap,
-			ShortHelp:  "Print DERP map",
-		},
-		{
-			Name:       "component-logs",
-			ShortUsage: "tailscale debug component-logs [" + strings.Join(ipn.DebuggableComponents, "|") + "]",
-			Exec:       runDebugComponentLogs,
-			ShortHelp:  "Enable/disable debug logs for a component",
-			FlagSet: (func() *flag.FlagSet {
-				fs := newFlagSet("component-logs")
-				fs.DurationVar(&debugComponentLogsArgs.forDur, "for", time.Hour, "how long to enable debug logs for; zero or negative means to disable")
-				return fs
-			})(),
-		},
-		{
-			Name:       "daemon-goroutines",
-			ShortUsage: "tailscale debug daemon-goroutines",
-			Exec:       runDaemonGoroutines,
-			ShortHelp:  "Print tailscaled's goroutines",
-		},
-		{
-			Name:       "daemon-logs",
-			ShortUsage: "tailscale debug daemon-logs",
-			Exec:       runDaemonLogs,
-			ShortHelp:  "Watch tailscaled's server logs",
-			FlagSet: (func() *flag.FlagSet {
-				fs := newFlagSet("daemon-logs")
-				fs.IntVar(&daemonLogsArgs.verbose, "verbose", 0, "verbosity level")
-				fs.BoolVar(&daemonLogsArgs.time, "time", false, "include client time")
-				return fs
-			})(),
-		},
-		{
-			Name:       "metrics",
-			ShortUsage: "tailscale debug metrics",
-			Exec:       runDaemonMetrics,
-			ShortHelp:  "Print tailscaled's metrics",
-			FlagSet: (func() *flag.FlagSet {
-				fs := newFlagSet("metrics")
-				fs.BoolVar(&metricsArgs.watch, "watch", false, "print JSON dump of delta values")
-				return fs
-			})(),
-		},
-		{
-			Name:       "env",
-			ShortUsage: "tailscale debug env",
-			Exec:       runEnv,
-			ShortHelp:  "Print cmd/tailscale environment",
-		},
-		{
-			Name:       "stat",
-			ShortUsage: "tailscale debug stat <files...>",
-			Exec:       runStat,
-			ShortHelp:  "Stat a file",
-		},
-		{
-			Name:       "hostinfo",
-			ShortUsage: "tailscale debug hostinfo",
-			Exec:       runHostinfo,
-			ShortHelp:  "Print hostinfo",
-		},
-		{
-			Name:       "local-creds",
-			ShortUsage: "tailscale debug local-creds",
-			Exec:       runLocalCreds,
-			ShortHelp:  "Print how to access Tailscale LocalAPI",
-		},
-		{
-			Name:       "restun",
-			ShortUsage: "tailscale debug restun",
-			Exec:       localAPIAction("restun"),
-			ShortHelp:  "Force a magicsock restun",
-		},
-		{
-			Name:       "rebind",
-			ShortUsage: "tailscale debug rebind",
-			Exec:       localAPIAction("rebind"),
-			ShortHelp:  "Force a magicsock rebind",
-		},
-		{
-			Name:       "derp-set-on-demand",
-			ShortUsage: "tailscale debug derp-set-on-demand",
-			Exec:       localAPIAction("derp-set-homeless"),
-			ShortHelp:  "Enable DERP on-demand mode (breaks reachability)",
-		},
-		{
-			Name:       "derp-unset-on-demand",
-			ShortUsage: "tailscale debug derp-unset-on-demand",
-			Exec:       localAPIAction("derp-unset-homeless"),
-			ShortHelp:  "Disable DERP on-demand mode",
-		},
-		{
-			Name:       "break-tcp-conns",
-			ShortUsage: "tailscale debug break-tcp-conns",
-			Exec:       localAPIAction("break-tcp-conns"),
-			ShortHelp:  "Break any open TCP connections from the daemon",
-		},
-		{
-			Name:       "break-derp-conns",
-			ShortUsage: "tailscale debug break-derp-conns",
-			Exec:       localAPIAction("break-derp-conns"),
-			ShortHelp:  "Break any open DERP connections from the daemon",
-		},
-		{
-			Name:       "pick-new-derp",
-			ShortUsage: "tailscale debug pick-new-derp",
-			Exec:       localAPIAction("pick-new-derp"),
-			ShortHelp:  "Switch to some other random DERP home region for a short time",
-		},
-		{
-			Name:       "force-prefer-derp",
-			ShortUsage: "tailscale debug force-prefer-derp",
-			Exec:       forcePreferDERP,
-			ShortHelp:  "Prefer the given region ID if reachable (until restart, or 0 to clear)",
-		},
-		{
-			Name:       "force-netmap-update",
-			ShortUsage: "tailscale debug force-netmap-update",
-			Exec:       localAPIAction("force-netmap-update"),
-			ShortHelp:  "Force a full no-op netmap update (for load testing)",
-		},
-		{
-			// TODO(bradfitz,maisem): eventually promote this out of debug
-			Name:       "reload-config",
-			ShortUsage: "tailscale debug reload-config",
-			Exec:       reloadConfig,
-			ShortHelp:  "Reload config",
-		},
-		{
-			Name:       "control-knobs",
-			ShortUsage: "tailscale debug control-knobs",
-			Exec:       debugControlKnobs,
-			ShortHelp:  "See current control knobs",
-		},
-		{
-			Name:       "prefs",
-			ShortUsage: "tailscale debug prefs",
-			Exec:       runPrefs,
-			ShortHelp:  "Print prefs",
-			FlagSet: (func() *flag.FlagSet {
-				fs := newFlagSet("prefs")
-				fs.BoolVar(&prefsArgs.pretty, "pretty", false, "If true, pretty-print output")
-				return fs
-			})(),
-		},
-		{
-			Name:       "watch-ipn",
-			ShortUsage: "tailscale debug watch-ipn",
-			Exec:       runWatchIPN,
-			ShortHelp:  "Subscribe to IPN message bus",
-			FlagSet: (func() *flag.FlagSet {
-				fs := newFlagSet("watch-ipn")
-				fs.BoolVar(&watchIPNArgs.netmap, "netmap", true, "include netmap in messages")
-				fs.BoolVar(&watchIPNArgs.initial, "initial", false, "include initial status")
-				fs.BoolVar(&watchIPNArgs.rateLimit, "rate-limit", true, "rate limit messags")
-				fs.BoolVar(&watchIPNArgs.showPrivateKey, "show-private-key", false, "include node private key in printed netmap")
-				fs.IntVar(&watchIPNArgs.count, "count", 0, "exit after printing this many statuses, or 0 to keep going forever")
-				return fs
-			})(),
-		},
-		{
-			Name:       "netmap",
-			ShortUsage: "tailscale debug netmap",
-			Exec:       runNetmap,
-			ShortHelp:  "Print the current network map",
-			FlagSet: (func() *flag.FlagSet {
-				fs := newFlagSet("netmap")
-				fs.BoolVar(&netmapArgs.showPrivateKey, "show-private-key", false, "include node private key in printed netmap")
-				return fs
-			})(),
-		},
-		{
-			Name: "via",
-			ShortUsage: "tailscale debug via <site-id> <v4-cidr>\n" +
-				"tailscale debug via <v6-route>",
-			Exec:      runVia,
-			ShortHelp: "Convert between site-specific IPv4 CIDRs and IPv6 'via' routes",
-		},
-		{
-			Name:       "ts2021",
-			ShortUsage: "tailscale debug ts2021",
-			Exec:       runTS2021,
-			ShortHelp:  "Debug ts2021 protocol connectivity",
-			FlagSet: (func() *flag.FlagSet {
-				fs := newFlagSet("ts2021")
-				fs.StringVar(&ts2021Args.host, "host", "controlplane.tailscale.com", "hostname of control plane")
-				fs.IntVar(&ts2021Args.version, "version", int(tailcfg.CurrentCapabilityVersion), "protocol version")
-				fs.BoolVar(&ts2021Args.verbose, "verbose", false, "be extra verbose")
-				return fs
-			})(),
-		},
-		{
-			Name:       "set-expire",
-			ShortUsage: "tailscale debug set-expire --in=1m",
-			Exec:       runSetExpire,
-			ShortHelp:  "Manipulate node key expiry for testing",
-			FlagSet: (func() *flag.FlagSet {
-				fs := newFlagSet("set-expire")
-				fs.DurationVar(&setExpireArgs.in, "in", 0, "if non-zero, set node key to expire this duration from now")
-				return fs
-			})(),
-		},
-		{
-			Name:       "dev-store-set",
-			ShortUsage: "tailscale debug dev-store-set",
-			Exec:       runDevStoreSet,
-			ShortHelp:  "Set a key/value pair during development",
-			FlagSet: (func() *flag.FlagSet {
-				fs := newFlagSet("store-set")
-				fs.BoolVar(&devStoreSetArgs.danger, "danger", false, "accept danger")
-				return fs
-			})(),
-		},
-		{
-			Name:       "derp",
-			ShortUsage: "tailscale debug derp",
-			Exec:       runDebugDERP,
-			ShortHelp:  "Test a DERP configuration",
-		},
-		{
-			Name:       "capture",
-			ShortUsage: "tailscale debug capture",
-			Exec:       runCapture,
-			ShortHelp:  "Streams pcaps for debugging",
-			FlagSet: (func() *flag.FlagSet {
-				fs := newFlagSet("capture")
-				fs.StringVar(&captureArgs.outFile, "o", "", "path to stream the pcap (or - for stdout), leave empty to start wireshark")
-				return fs
-			})(),
-		},
-		{
-			Name:       "portmap",
-			ShortUsage: "tailscale debug portmap",
-			Exec:       debugPortmap,
-			ShortHelp:  "Run portmap debugging",
-			FlagSet: (func() *flag.FlagSet {
-				fs := newFlagSet("portmap")
-				fs.DurationVar(&debugPortmapArgs.duration, "duration", 5*time.Second, "timeout for port mapping")
-				fs.StringVar(&debugPortmapArgs.ty, "type", "", `portmap debug type (one of "", "pmp", "pcp", or "upnp")`)
-				fs.StringVar(&debugPortmapArgs.gatewayAddr, "gateway-addr", "", `override gateway IP (must also pass --self-addr)`)
-				fs.StringVar(&debugPortmapArgs.selfAddr, "self-addr", "", `override self IP (must also pass --gateway-addr)`)
-				fs.BoolVar(&debugPortmapArgs.logHTTP, "log-http", false, `print all HTTP requests and responses to the log`)
-				return fs
-			})(),
-		},
-		{
-			Name:       "peer-endpoint-changes",
-			ShortUsage: "tailscale debug peer-endpoint-changes <hostname-or-IP>",
-			Exec:       runPeerEndpointChanges,
-			ShortHelp:  "Prints debug information about a peer's endpoint changes",
-		},
-		{
-			Name:       "dial-types",
-			ShortUsage: "tailscale debug dial-types <hostname-or-IP> <port>",
-			Exec:       runDebugDialTypes,
-			ShortHelp:  "Prints debug information about connecting to a given host or IP",
-			FlagSet: (func() *flag.FlagSet {
-				fs := newFlagSet("dial-types")
-				fs.StringVar(&debugDialTypesArgs.network, "network", "tcp", `network type to dial ("tcp", "udp", etc.)`)
-				return fs
-			})(),
-		},
-		{
-			Name:       "resolve",
-			ShortUsage: "tailscale debug resolve <hostname>",
-			Exec:       runDebugResolve,
-			ShortHelp:  "Does a DNS lookup",
-			FlagSet: (func() *flag.FlagSet {
-				fs := newFlagSet("resolve")
-				fs.StringVar(&resolveArgs.net, "net", "ip", "network type to resolve (ip, ip4, ip6)")
-				return fs
-			})(),
-		},
-		{
-			Name:       "go-buildinfo",
-			ShortUsage: "tailscale debug go-buildinfo",
-			ShortHelp:  "Prints Go's runtime/debug.BuildInfo",
-			Exec:       runGoBuildInfo,
-		},
-	},
+var (
+	debugCaptureCmd func() *ffcli.Command // or nil
+)
+
+func debugCmd() *ffcli.Command {
+	return &ffcli.Command{
+		Name:       "debug",
+		Exec:       runDebug,
+		ShortUsage: "tailscale debug <debug-flags | subcommand>",
+		ShortHelp:  "Debug commands",
+		LongHelp:   hidden + `"tailscale debug" contains misc debug facilities; it is not a stable interface.`,
+		FlagSet: (func() *flag.FlagSet {
+			fs := newFlagSet("debug")
+			fs.StringVar(&debugArgs.file, "file", "", "get, delete:NAME, or NAME")
+			fs.StringVar(&debugArgs.cpuFile, "cpu-profile", "", "if non-empty, grab a CPU profile for --profile-seconds seconds and write it to this file; - for stdout")
+			fs.StringVar(&debugArgs.memFile, "mem-profile", "", "if non-empty, grab a memory profile and write it to this file; - for stdout")
+			fs.IntVar(&debugArgs.cpuSec, "profile-seconds", 15, "number of seconds to run a CPU profile for, when --cpu-profile is non-empty")
+			return fs
+		})(),
+		Subcommands: nonNilCmds([]*ffcli.Command{
+			{
+				Name:       "derp-map",
+				ShortUsage: "tailscale debug derp-map",
+				Exec:       runDERPMap,
+				ShortHelp:  "Print DERP map",
+			},
+			{
+				Name:       "component-logs",
+				ShortUsage: "tailscale debug component-logs [" + strings.Join(ipn.DebuggableComponents, "|") + "]",
+				Exec:       runDebugComponentLogs,
+				ShortHelp:  "Enable/disable debug logs for a component",
+				FlagSet: (func() *flag.FlagSet {
+					fs := newFlagSet("component-logs")
+					fs.DurationVar(&debugComponentLogsArgs.forDur, "for", time.Hour, "how long to enable debug logs for; zero or negative means to disable")
+					return fs
+				})(),
+			},
+			{
+				Name:       "daemon-goroutines",
+				ShortUsage: "tailscale debug daemon-goroutines",
+				Exec:       runDaemonGoroutines,
+				ShortHelp:  "Print tailscaled's goroutines",
+			},
+			{
+				Name:       "daemon-logs",
+				ShortUsage: "tailscale debug daemon-logs",
+				Exec:       runDaemonLogs,
+				ShortHelp:  "Watch tailscaled's server logs",
+				FlagSet: (func() *flag.FlagSet {
+					fs := newFlagSet("daemon-logs")
+					fs.IntVar(&daemonLogsArgs.verbose, "verbose", 0, "verbosity level")
+					fs.BoolVar(&daemonLogsArgs.time, "time", false, "include client time")
+					return fs
+				})(),
+			},
+			{
+				Name:       "metrics",
+				ShortUsage: "tailscale debug metrics",
+				Exec:       runDaemonMetrics,
+				ShortHelp:  "Print tailscaled's metrics",
+				FlagSet: (func() *flag.FlagSet {
+					fs := newFlagSet("metrics")
+					fs.BoolVar(&metricsArgs.watch, "watch", false, "print JSON dump of delta values")
+					return fs
+				})(),
+			},
+			{
+				Name:       "env",
+				ShortUsage: "tailscale debug env",
+				Exec:       runEnv,
+				ShortHelp:  "Print cmd/tailscale environment",
+			},
+			{
+				Name:       "stat",
+				ShortUsage: "tailscale debug stat <files...>",
+				Exec:       runStat,
+				ShortHelp:  "Stat a file",
+			},
+			{
+				Name:       "hostinfo",
+				ShortUsage: "tailscale debug hostinfo",
+				Exec:       runHostinfo,
+				ShortHelp:  "Print hostinfo",
+			},
+			{
+				Name:       "local-creds",
+				ShortUsage: "tailscale debug local-creds",
+				Exec:       runLocalCreds,
+				ShortHelp:  "Print how to access Tailscale LocalAPI",
+			},
+			{
+				Name:       "restun",
+				ShortUsage: "tailscale debug restun",
+				Exec:       localAPIAction("restun"),
+				ShortHelp:  "Force a magicsock restun",
+			},
+			{
+				Name:       "rebind",
+				ShortUsage: "tailscale debug rebind",
+				Exec:       localAPIAction("rebind"),
+				ShortHelp:  "Force a magicsock rebind",
+			},
+			{
+				Name:       "derp-set-on-demand",
+				ShortUsage: "tailscale debug derp-set-on-demand",
+				Exec:       localAPIAction("derp-set-homeless"),
+				ShortHelp:  "Enable DERP on-demand mode (breaks reachability)",
+			},
+			{
+				Name:       "derp-unset-on-demand",
+				ShortUsage: "tailscale debug derp-unset-on-demand",
+				Exec:       localAPIAction("derp-unset-homeless"),
+				ShortHelp:  "Disable DERP on-demand mode",
+			},
+			{
+				Name:       "break-tcp-conns",
+				ShortUsage: "tailscale debug break-tcp-conns",
+				Exec:       localAPIAction("break-tcp-conns"),
+				ShortHelp:  "Break any open TCP connections from the daemon",
+			},
+			{
+				Name:       "break-derp-conns",
+				ShortUsage: "tailscale debug break-derp-conns",
+				Exec:       localAPIAction("break-derp-conns"),
+				ShortHelp:  "Break any open DERP connections from the daemon",
+			},
+			{
+				Name:       "pick-new-derp",
+				ShortUsage: "tailscale debug pick-new-derp",
+				Exec:       localAPIAction("pick-new-derp"),
+				ShortHelp:  "Switch to some other random DERP home region for a short time",
+			},
+			{
+				Name:       "force-prefer-derp",
+				ShortUsage: "tailscale debug force-prefer-derp",
+				Exec:       forcePreferDERP,
+				ShortHelp:  "Prefer the given region ID if reachable (until restart, or 0 to clear)",
+			},
+			{
+				Name:       "force-netmap-update",
+				ShortUsage: "tailscale debug force-netmap-update",
+				Exec:       localAPIAction("force-netmap-update"),
+				ShortHelp:  "Force a full no-op netmap update (for load testing)",
+			},
+			{
+				// TODO(bradfitz,maisem): eventually promote this out of debug
+				Name:       "reload-config",
+				ShortUsage: "tailscale debug reload-config",
+				Exec:       reloadConfig,
+				ShortHelp:  "Reload config",
+			},
+			{
+				Name:       "control-knobs",
+				ShortUsage: "tailscale debug control-knobs",
+				Exec:       debugControlKnobs,
+				ShortHelp:  "See current control knobs",
+			},
+			{
+				Name:       "prefs",
+				ShortUsage: "tailscale debug prefs",
+				Exec:       runPrefs,
+				ShortHelp:  "Print prefs",
+				FlagSet: (func() *flag.FlagSet {
+					fs := newFlagSet("prefs")
+					fs.BoolVar(&prefsArgs.pretty, "pretty", false, "If true, pretty-print output")
+					return fs
+				})(),
+			},
+			{
+				Name:       "watch-ipn",
+				ShortUsage: "tailscale debug watch-ipn",
+				Exec:       runWatchIPN,
+				ShortHelp:  "Subscribe to IPN message bus",
+				FlagSet: (func() *flag.FlagSet {
+					fs := newFlagSet("watch-ipn")
+					fs.BoolVar(&watchIPNArgs.netmap, "netmap", true, "include netmap in messages")
+					fs.BoolVar(&watchIPNArgs.initial, "initial", false, "include initial status")
+					fs.BoolVar(&watchIPNArgs.rateLimit, "rate-limit", true, "rate limit messags")
+					fs.BoolVar(&watchIPNArgs.showPrivateKey, "show-private-key", false, "include node private key in printed netmap")
+					fs.IntVar(&watchIPNArgs.count, "count", 0, "exit after printing this many statuses, or 0 to keep going forever")
+					return fs
+				})(),
+			},
+			{
+				Name:       "netmap",
+				ShortUsage: "tailscale debug netmap",
+				Exec:       runNetmap,
+				ShortHelp:  "Print the current network map",
+				FlagSet: (func() *flag.FlagSet {
+					fs := newFlagSet("netmap")
+					fs.BoolVar(&netmapArgs.showPrivateKey, "show-private-key", false, "include node private key in printed netmap")
+					return fs
+				})(),
+			},
+			{
+				Name: "via",
+				ShortUsage: "tailscale debug via <site-id> <v4-cidr>\n" +
+					"tailscale debug via <v6-route>",
+				Exec:      runVia,
+				ShortHelp: "Convert between site-specific IPv4 CIDRs and IPv6 'via' routes",
+			},
+			{
+				Name:       "ts2021",
+				ShortUsage: "tailscale debug ts2021",
+				Exec:       runTS2021,
+				ShortHelp:  "Debug ts2021 protocol connectivity",
+				FlagSet: (func() *flag.FlagSet {
+					fs := newFlagSet("ts2021")
+					fs.StringVar(&ts2021Args.host, "host", "controlplane.tailscale.com", "hostname of control plane")
+					fs.IntVar(&ts2021Args.version, "version", int(tailcfg.CurrentCapabilityVersion), "protocol version")
+					fs.BoolVar(&ts2021Args.verbose, "verbose", false, "be extra verbose")
+					return fs
+				})(),
+			},
+			{
+				Name:       "set-expire",
+				ShortUsage: "tailscale debug set-expire --in=1m",
+				Exec:       runSetExpire,
+				ShortHelp:  "Manipulate node key expiry for testing",
+				FlagSet: (func() *flag.FlagSet {
+					fs := newFlagSet("set-expire")
+					fs.DurationVar(&setExpireArgs.in, "in", 0, "if non-zero, set node key to expire this duration from now")
+					return fs
+				})(),
+			},
+			{
+				Name:       "dev-store-set",
+				ShortUsage: "tailscale debug dev-store-set",
+				Exec:       runDevStoreSet,
+				ShortHelp:  "Set a key/value pair during development",
+				FlagSet: (func() *flag.FlagSet {
+					fs := newFlagSet("store-set")
+					fs.BoolVar(&devStoreSetArgs.danger, "danger", false, "accept danger")
+					return fs
+				})(),
+			},
+			{
+				Name:       "derp",
+				ShortUsage: "tailscale debug derp",
+				Exec:       runDebugDERP,
+				ShortHelp:  "Test a DERP configuration",
+			},
+			ccall(debugCaptureCmd),
+			{
+				Name:       "portmap",
+				ShortUsage: "tailscale debug portmap",
+				Exec:       debugPortmap,
+				ShortHelp:  "Run portmap debugging",
+				FlagSet: (func() *flag.FlagSet {
+					fs := newFlagSet("portmap")
+					fs.DurationVar(&debugPortmapArgs.duration, "duration", 5*time.Second, "timeout for port mapping")
+					fs.StringVar(&debugPortmapArgs.ty, "type", "", `portmap debug type (one of "", "pmp", "pcp", or "upnp")`)
+					fs.StringVar(&debugPortmapArgs.gatewayAddr, "gateway-addr", "", `override gateway IP (must also pass --self-addr)`)
+					fs.StringVar(&debugPortmapArgs.selfAddr, "self-addr", "", `override self IP (must also pass --gateway-addr)`)
+					fs.BoolVar(&debugPortmapArgs.logHTTP, "log-http", false, `print all HTTP requests and responses to the log`)
+					return fs
+				})(),
+			},
+			{
+				Name:       "peer-endpoint-changes",
+				ShortUsage: "tailscale debug peer-endpoint-changes <hostname-or-IP>",
+				Exec:       runPeerEndpointChanges,
+				ShortHelp:  "Print debug information about a peer's endpoint changes",
+			},
+			{
+				Name:       "dial-types",
+				ShortUsage: "tailscale debug dial-types <hostname-or-IP> <port>",
+				Exec:       runDebugDialTypes,
+				ShortHelp:  "Print debug information about connecting to a given host or IP",
+				FlagSet: (func() *flag.FlagSet {
+					fs := newFlagSet("dial-types")
+					fs.StringVar(&debugDialTypesArgs.network, "network", "tcp", `network type to dial ("tcp", "udp", etc.)`)
+					return fs
+				})(),
+			},
+			{
+				Name:       "resolve",
+				ShortUsage: "tailscale debug resolve <hostname>",
+				Exec:       runDebugResolve,
+				ShortHelp:  "Does a DNS lookup",
+				FlagSet: (func() *flag.FlagSet {
+					fs := newFlagSet("resolve")
+					fs.StringVar(&resolveArgs.net, "net", "ip", "network type to resolve (ip, ip4, ip6)")
+					return fs
+				})(),
+			},
+			{
+				Name:       "go-buildinfo",
+				ShortUsage: "tailscale debug go-buildinfo",
+				ShortHelp:  "Print Go's runtime/debug.BuildInfo",
+				Exec:       runGoBuildInfo,
+			},
+		}...),
+	}
 }
 
 func runGoBuildInfo(ctx context.Context, args []string) error {
@@ -1036,50 +1030,6 @@ func runSetExpire(ctx context.Context, args []string) error {
 	return localClient.DebugSetExpireIn(ctx, setExpireArgs.in)
 }
 
-var captureArgs struct {
-	outFile string
-}
-
-func runCapture(ctx context.Context, args []string) error {
-	stream, err := localClient.StreamDebugCapture(ctx)
-	if err != nil {
-		return err
-	}
-	defer stream.Close()
-
-	switch captureArgs.outFile {
-	case "-":
-		fmt.Fprintln(Stderr, "Press Ctrl-C to stop the capture.")
-		_, err = io.Copy(os.Stdout, stream)
-		return err
-	case "":
-		lua, err := os.CreateTemp("", "ts-dissector")
-		if err != nil {
-			return err
-		}
-		defer os.Remove(lua.Name())
-		lua.Write([]byte(capture.DissectorLua))
-		if err := lua.Close(); err != nil {
-			return err
-		}
-
-		wireshark := exec.CommandContext(ctx, "wireshark", "-X", "lua_script:"+lua.Name(), "-k", "-i", "-")
-		wireshark.Stdin = stream
-		wireshark.Stdout = os.Stdout
-		wireshark.Stderr = os.Stderr
-		return wireshark.Run()
-	}
-
-	f, err := os.OpenFile(captureArgs.outFile, os.O_WRONLY|os.O_CREATE|os.O_TRUNC, 0644)
-	if err != nil {
-		return err
-	}
-	defer f.Close()
-	fmt.Fprintln(Stderr, "Press Ctrl-C to stop the capture.")
-	_, err = io.Copy(f, stream)
-	return err
-}
-
 var debugPortmapArgs struct {
 	duration    time.Duration
 	gatewayAddr string

cmd/tailscale/cli/dns.go

@@ -20,7 +20,7 @@ var dnsCmd = &ffcli.Command{
 			Name:       "status",
 			ShortUsage: "tailscale dns status [--all]",
 			Exec:       runDNSStatus,
-			ShortHelp:  "Prints the current DNS status and configuration",
+			ShortHelp:  "Print the current DNS status and configuration",
 			LongHelp:   dnsStatusLongHelp(),
 			FlagSet: (func() *flag.FlagSet {
 				fs := newFlagSet("status")