version/mkversion: override patch version to 1

Commit used for auto-update testing.

.github/workflows/checklocks.yml

@@ -0,0 +1,28 @@
+name: checklocks
+
+on:
+  push:
+    branches:
+      - main
+  pull_request:
+    paths:
+      - '**/*.go'
+      - '.github/workflows/checklocks.yml'
+
+concurrency:
+  group: ${{ github.workflow }}-$${{ github.head_ref || github.run_id }}
+  cancel-in-progress: true
+
+jobs:
+  checklocks:
+    runs-on: [ ubuntu-latest ]
+    steps:
+      - name: Check out code
+        uses: actions/checkout@v4
+
+      - name: Build checklocks
+        run: ./tool/go build -o /tmp/checklocks gvisor.dev/gvisor/tools/checklocks/cmd/checklocks
+
+      - name: Run checklocks vet
+        # TODO: remove || true once we have applied checklocks annotations everywhere.
+        run: ./tool/go vet -vettool=/tmp/checklocks ./... || true

.github/workflows/golangci-lint.yml

@@ -31,10 +31,10 @@ jobs:
           cache: false
 
       - name: golangci-lint
-        # Note: this is the 'v3' tag as of 2023-04-17
+        # Note: this is the 'v3' tag as of 2023-08-14
         uses: golangci/golangci-lint-action@639cd343e1d3b897ff35927a75193d57cfcba299
         with:
-          version: v1.52.2
+          version: v1.54.2
 
           # Show only new issues if it's a pull request.
           only-new-issues: true

.github/workflows/kubemanifests.yaml

@@ -0,0 +1,24 @@
+name: "Kubernetes manifests"
+on:
+  pull_request:
+   paths: 
+   - './cmd/k8s-operator/'
+   - '.github/workflows/kubemanifests.yaml'
+
+# Cancel workflow run if there is a newer push to the same PR for which it is
+# running
+concurrency:
+  group: ${{ github.workflow }}-$${{ github.head_ref || github.run_id }}
+  cancel-in-progress: true
+
+jobs:
+  testchart:
+    runs-on: [ ubuntu-latest ]
+    steps:
+    - name: Check out code
+      uses: actions/checkout@v4
+    - name: Build and lint Helm chart
+      run: |
+        eval `./tool/go run ./cmd/mkversion`
+        ./tool/helm package --app-version="${VERSION_SHORT}" --version=${VERSION_SHORT} './cmd/k8s-operator/deploy/chart'
+        ./tool/helm lint "tailscale-operator-${VERSION_SHORT}.tgz"

.github/workflows/test.yml

@@ -22,8 +22,7 @@ on:
       - "main"
       - "release-branch/*"
   pull_request:
-    branches:
-      - "*"
+    # all PRs on all branches
   merge_group:
     branches:
       - "main"
@@ -39,6 +38,26 @@ concurrency:
   cancel-in-progress: true
 
 jobs:
+  race-root-integration:
+    runs-on: ubuntu-22.04
+    strategy:
+      fail-fast: false # don't abort the entire matrix if one element fails
+      matrix:
+        include:
+          - shard: '1/4'
+          - shard: '2/4'
+          - shard: '3/4'
+          - shard: '4/4'
+    steps:
+    - name: checkout
+      uses: actions/checkout@v4
+    - name: build test wrapper
+      run: ./tool/go build -o /tmp/testwrapper ./cmd/testwrapper
+    - name: integration tests as root
+      run: PATH=$PWD/tool:$PATH /tmp/testwrapper -exec "sudo -E" -race ./tstest/integration/
+      env:
+        TS_TEST_SHARD: ${{ matrix.shard }}
+
   test:
     strategy:
       fail-fast: false # don't abort the entire matrix if one element fails
@@ -47,6 +66,13 @@ jobs:
           - goarch: amd64
           - goarch: amd64
             buildflags: "-race"
+            shard: '1/3'
+          - goarch: amd64
+            buildflags: "-race"
+            shard: '2/3'
+          - goarch: amd64
+            buildflags: "-race"
+            shard: '3/3'
           - goarch: "386" # thanks yaml
     runs-on: ubuntu-22.04
     steps:
@@ -70,6 +96,7 @@ jobs:
           ${{ github.job }}-${{ runner.os }}-${{ matrix.goarch }}-${{ matrix.buildflags }}-go-2-${{ hashFiles('**/go.sum') }}
           ${{ github.job }}-${{ runner.os }}-${{ matrix.goarch }}-${{ matrix.buildflags }}-go-2-
     - name: build all
+      if: matrix.buildflags == '' # skip on race builder
       run: ./tool/go build ${{matrix.buildflags}} ./...
       env:
         GOARCH: ${{ matrix.goarch }}
@@ -94,6 +121,7 @@ jobs:
       run: PATH=$PWD/tool:$PATH /tmp/testwrapper ./... ${{matrix.buildflags}}
       env:
         GOARCH: ${{ matrix.goarch }}
+        TS_TEST_SHARD: ${{ matrix.shard }}
     - name: bench all
       run: ./tool/go test ${{matrix.buildflags}} -bench=. -benchtime=1x -run=^$ $(for x in $(git grep -l "^func Benchmark" | xargs dirname | sort | uniq); do echo "./$x"; done)
       env:
@@ -162,7 +190,17 @@ jobs:
         HOME: "/tmp"
         TMPDIR: "/tmp"
         XDB_CACHE_HOME: "/var/lib/ghrunner/cache"
-  
+
+  race-build:
+    runs-on: ubuntu-22.04
+    steps:
+    - name: checkout
+      uses: actions/checkout@v4
+    - name: build all
+      run: ./tool/go install -race ./cmd/...
+    - name: build tests
+      run: ./tool/go test -race -exec=true ./...
+
   cross: # cross-compile checks, build only.
     strategy:
       fail-fast: false # don't abort the entire matrix if one element fails

VERSION.txt

@@ -1 +1 @@
-1.51.0
+1.53.0

api.md

@@ -209,10 +209,6 @@ You can also [list all devices in the tailnet](#list-tailnet-devices) to get the
       "192.68.0.21:59128"
     ],
 
-    // derp (string) is the IP:port of the DERP server currently being used.
-    // Learn about DERP servers at https://tailscale.com/kb/1232/.
-    "derp":"",
-
     // mappingVariesByDestIP (boolean) is 'true' if the host's NAT mappings
     // vary based on the destination IP.
     "mappingVariesByDestIP":false,

appc/appconnector.go

@@ -0,0 +1,174 @@
+// Copyright (c) Tailscale Inc & AUTHORS
+// SPDX-License-Identifier: BSD-3-Clause
+
+// Package appc implements App Connectors.
+// An AppConnector provides DNS domain oriented routing of traffic. An App
+// Connector becomes a DNS server for a peer, authoritative for the set of
+// configured domains. DNS resolution of the target domain triggers dynamic
+// publication of routes to ensure that traffic to the domain is routed through
+// the App Connector.
+package appc
+
+import (
+	"net/netip"
+	"slices"
+	"strings"
+	"sync"
+
+	xmaps "golang.org/x/exp/maps"
+	"golang.org/x/net/dns/dnsmessage"
+	"tailscale.com/types/logger"
+	"tailscale.com/types/views"
+)
+
+// RouteAdvertiser is an interface that allows the AppConnector to advertise
+// newly discovered routes that need to be served through the AppConnector.
+type RouteAdvertiser interface {
+	// AdvertiseRoute adds a new route advertisement if the route is not already
+	// being advertised.
+	AdvertiseRoute(netip.Prefix) error
+}
+
+// AppConnector is an implementation of an AppConnector that performs
+// its function as a subsystem inside of a tailscale node. At the control plane
+// side App Connector routing is configured in terms of domains rather than IP
+// addresses.
+// The AppConnectors responsibility inside tailscaled is to apply the routing
+// and domain configuration as supplied in the map response.
+// DNS requests for configured domains are observed. If the domains resolve to
+// routes not yet served by the AppConnector the local node configuration is
+// updated to advertise the new route.
+type AppConnector struct {
+	logf            logger.Logf
+	routeAdvertiser RouteAdvertiser
+
+	// mu guards the fields that follow
+	mu sync.Mutex
+	// domains is a map of lower case domain names with no trailing dot, to a
+	// list of resolved IP addresses.
+	domains map[string][]netip.Addr
+}
+
+// NewAppConnector creates a new AppConnector.
+func NewAppConnector(logf logger.Logf, routeAdvertiser RouteAdvertiser) *AppConnector {
+	return &AppConnector{
+		logf:            logger.WithPrefix(logf, "appc: "),
+		routeAdvertiser: routeAdvertiser,
+	}
+}
+
+// UpdateDomains replaces the current set of configured domains with the
+// supplied set of domains. Domains must not contain a trailing dot, and should
+// be lower case.
+func (e *AppConnector) UpdateDomains(domains []string) {
+	e.mu.Lock()
+	defer e.mu.Unlock()
+
+	var old map[string][]netip.Addr
+	old, e.domains = e.domains, make(map[string][]netip.Addr, len(domains))
+	for _, d := range domains {
+		d = strings.ToLower(d)
+		e.domains[d] = old[d]
+	}
+	e.logf("handling domains: %v", xmaps.Keys(e.domains))
+}
+
+// Domains returns the currently configured domain list.
+func (e *AppConnector) Domains() views.Slice[string] {
+	e.mu.Lock()
+	defer e.mu.Unlock()
+
+	return views.SliceOf(xmaps.Keys(e.domains))
+}
+
+// ObserveDNSResponse is a callback invoked by the DNS resolver when a DNS
+// 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) {
+	var p dnsmessage.Parser
+	if _, err := p.Start(res); err != nil {
+		return
+	}
+	if err := p.SkipAllQuestions(); err != nil {
+		return
+	}
+
+	for {
+		h, err := p.AnswerHeader()
+		if err == dnsmessage.ErrSectionDone {
+			break
+		}
+		if err != nil {
+			return
+		}
+
+		if h.Class != dnsmessage.ClassINET {
+			if err := p.SkipAnswer(); err != nil {
+				return
+			}
+			continue
+		}
+		if h.Type != dnsmessage.TypeA && h.Type != dnsmessage.TypeAAAA {
+			if err := p.SkipAnswer(); err != nil {
+				return
+			}
+			continue
+		}
+
+		domain := h.Name.String()
+		if len(domain) == 0 {
+			return
+		}
+		if domain[len(domain)-1] == '.' {
+			domain = domain[:len(domain)-1]
+		}
+		domain = strings.ToLower(domain)
+		e.logf("[v2] observed DNS response for %s", domain)
+
+		e.mu.Lock()
+		addrs, ok := e.domains[domain]
+		e.mu.Unlock()
+		if !ok {
+			if err := p.SkipAnswer(); err != nil {
+				return
+			}
+			continue
+		}
+
+		var addr netip.Addr
+		switch h.Type {
+		case dnsmessage.TypeA:
+			r, err := p.AResource()
+			if err != nil {
+				return
+			}
+			addr = netip.AddrFrom4(r.A)
+		case dnsmessage.TypeAAAA:
+			r, err := p.AAAAResource()
+			if err != nil {
+				return
+			}
+			addr = netip.AddrFrom16(r.AAAA)
+		default:
+			if err := p.SkipAnswer(); err != nil {
+				return
+			}
+			continue
+		}
+		if slices.Contains(addrs, addr) {
+			continue
+		}
+		// TODO(raggi): check for existing prefixes
+		if err := e.routeAdvertiser.AdvertiseRoute(netip.PrefixFrom(addr, addr.BitLen())); err != nil {
+			e.logf("failed to advertise route for %v: %v", addr, err)
+			continue
+		}
+		e.logf("[v2] advertised route for %v: %v", domain, addr)
+
+		e.mu.Lock()
+		e.domains[domain] = append(addrs, addr)
+		e.mu.Unlock()
+	}
+
+}

appc/appconnector_test.go

@@ -0,0 +1,118 @@
+// Copyright (c) Tailscale Inc & AUTHORS
+// SPDX-License-Identifier: BSD-3-Clause
+
+package appc
+
+import (
+	"net/netip"
+	"slices"
+	"testing"
+
+	xmaps "golang.org/x/exp/maps"
+	"golang.org/x/net/dns/dnsmessage"
+	"tailscale.com/util/must"
+)
+
+func TestUpdateDomains(t *testing.T) {
+	a := NewAppConnector(t.Logf, nil)
+	a.UpdateDomains([]string{"example.com"})
+	if got, want := a.Domains().AsSlice(), []string{"example.com"}; !slices.Equal(got, want) {
+		t.Errorf("got %v; want %v", got, want)
+	}
+
+	addr := netip.MustParseAddr("192.0.0.8")
+	a.domains["example.com"] = append(a.domains["example.com"], addr)
+	a.UpdateDomains([]string{"example.com"})
+
+	if got, want := a.domains["example.com"], []netip.Addr{addr}; !slices.Equal(got, want) {
+		t.Errorf("got %v; want %v", got, want)
+	}
+
+	// domains are explicitly downcased on set.
+	a.UpdateDomains([]string{"UP.EXAMPLE.COM"})
+	if got, want := xmaps.Keys(a.domains), []string{"up.example.com"}; !slices.Equal(got, want) {
+		t.Errorf("got %v; want %v", got, want)
+	}
+}
+
+func TestObserveDNSResponse(t *testing.T) {
+	rc := &routeCollector{}
+	a := NewAppConnector(t.Logf, rc)
+
+	// a has no domains configured, so it should not advertise any routes
+	a.ObserveDNSResponse(dnsResponse("example.com.", "192.0.0.8"))
+	if got, want := rc.routes, ([]netip.Prefix)(nil); !slices.Equal(got, want) {
+		t.Errorf("got %v; want %v", got, want)
+	}
+
+	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 got, want := rc.routes, wantRoutes; !slices.Equal(got, want) {
+		t.Errorf("got %v; want %v", got, want)
+	}
+
+	wantRoutes = append(wantRoutes, netip.MustParsePrefix("2001:db8::1/128"))
+
+	a.ObserveDNSResponse(dnsResponse("example.com.", "2001:db8::1"))
+	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 !slices.Equal(rc.routes, wantRoutes) {
+		t.Errorf("got %v; want %v", rc.routes, wantRoutes)
+	}
+}
+
+// dnsResponse is a test helper that creates a DNS response buffer for the given domain and address
+func dnsResponse(domain, address string) []byte {
+	addr := netip.MustParseAddr(address)
+	b := dnsmessage.NewBuilder(nil, dnsmessage.Header{})
+	b.EnableCompression()
+	b.StartAnswers()
+	switch addr.BitLen() {
+	case 32:
+		b.AResource(
+			dnsmessage.ResourceHeader{
+				Name:  dnsmessage.MustNewName(domain),
+				Type:  dnsmessage.TypeA,
+				Class: dnsmessage.ClassINET,
+				TTL:   0,
+			},
+			dnsmessage.AResource{
+				A: addr.As4(),
+			},
+		)
+	case 128:
+		b.AAAAResource(
+			dnsmessage.ResourceHeader{
+				Name:  dnsmessage.MustNewName(domain),
+				Type:  dnsmessage.TypeAAAA,
+				Class: dnsmessage.ClassINET,
+				TTL:   0,
+			},
+			dnsmessage.AAAAResource{
+				AAAA: addr.As16(),
+			},
+		)
+	default:
+		panic("invalid address length")
+	}
+	return must.Get(b.Finish())
+}
+
+// routeCollector is a test helper that collects the list of routes advertised
+type routeCollector struct {
+	routes []netip.Prefix
+}
+
+// routeCollector implements RouteAdvertiser
+var _ RouteAdvertiser = (*routeCollector)(nil)
+
+func (rc *routeCollector) AdvertiseRoute(pfx netip.Prefix) error {
+	rc.routes = append(rc.routes, pfx)
+	return nil
+}

client/tailscale/apitype/apitype.go

@@ -40,3 +40,12 @@ type SetPushDeviceTokenRequest struct {
 	// PushDeviceToken is the iOS/macOS APNs device token (and any future Android equivalent).
 	PushDeviceToken string
 }
+
+// ReloadConfigResponse is the response to a LocalAPI reload-config request.
+//
+// There are three possible outcomes: (false, "") if no config mode in use,
+// (true, "") on success, or (false, "error message") on failure.
+type ReloadConfigResponse struct {
+	Reloaded bool   // whether the config was reloaded
+	Err      string // any error message
+}

client/tailscale/localclient.go

@@ -1244,6 +1244,22 @@ func (lc *LocalClient) ProfileStatus(ctx context.Context) (current ipn.LoginProf
 	return current, all, err
 }
 
+// ReloadConfig reloads the config file, if possible.
+func (lc *LocalClient) ReloadConfig(ctx context.Context) (ok bool, err error) {
+	body, err := lc.send(ctx, "POST", "/localapi/v0/reload-config", 200, nil)
+	if err != nil {
+		return
+	}
+	res, err := decodeJSON[apitype.ReloadConfigResponse](body)
+	if err != nil {
+		return
+	}
+	if res.Err != "" {
+		return false, errors.New(res.Err)
+	}
+	return res.Reloaded, nil
+}
+
 // SwitchToEmptyProfile creates and switches to a new unnamed profile. The new
 // profile is not assigned an ID until it is persisted after a successful login.
 // In order to login to the new profile, the user must call LoginInteractive.

client/web/auth.go

@@ -0,0 +1,248 @@
+// Copyright (c) Tailscale Inc & AUTHORS
+// SPDX-License-Identifier: BSD-3-Clause
+
+package web
+
+import (
+	"bytes"
+	"context"
+	"crypto/rand"
+	"encoding/base64"
+	"encoding/json"
+	"errors"
+	"fmt"
+	"io"
+	"net/http"
+	"time"
+
+	"tailscale.com/client/tailscale/apitype"
+	"tailscale.com/tailcfg"
+)
+
+const (
+	sessionCookieName   = "TS-Web-Session"
+	sessionCookieExpiry = time.Hour * 24 * 30 // 30 days
+)
+
+// browserSession holds data about a user's browser session
+// on the full management web client.
+type browserSession struct {
+	// ID is the unique identifier for the session.
+	// It is passed in the user's "TS-Web-Session" browser cookie.
+	ID            string
+	SrcNode       tailcfg.NodeID
+	SrcUser       tailcfg.UserID
+	AuthID        string // from tailcfg.WebClientAuthResponse
+	AuthURL       string // from tailcfg.WebClientAuthResponse
+	Created       time.Time
+	Authenticated bool
+}
+
+// isAuthorized reports true if the given session is authorized
+// to be used by its associated user to access the full management
+// web client.
+//
+// isAuthorized is true only when s.Authenticated is true (i.e.
+// the user has authenticated the session) and the session is not
+// expired.
+// 2023-10-05: Sessions expire by default 30 days after creation.
+func (s *browserSession) isAuthorized(now time.Time) bool {
+	switch {
+	case s == nil:
+		return false
+	case !s.Authenticated:
+		return false // awaiting auth
+	case s.isExpired(now):
+		return false // expired
+	}
+	return true
+}
+
+// isExpired reports true if s is expired.
+// 2023-10-05: Sessions expire by default 30 days after creation.
+func (s *browserSession) isExpired(now time.Time) bool {
+	return !s.Created.IsZero() && now.After(s.expires())
+}
+
+// expires reports when the given session expires.
+func (s *browserSession) expires() time.Time {
+	return s.Created.Add(sessionCookieExpiry)
+}
+
+var (
+	errNoSession          = errors.New("no-browser-session")
+	errNotUsingTailscale  = errors.New("not-using-tailscale")
+	errTaggedRemoteSource = errors.New("tagged-remote-source")
+	errTaggedLocalSource  = errors.New("tagged-local-source")
+	errNotOwner           = errors.New("not-owner")
+)
+
+// getSession retrieves the browser session associated with the request,
+// if one exists.
+//
+// An error is returned in any of the following cases:
+//
+//   - (errNotUsingTailscale) The request was not made over tailscale.
+//
+//   - (errNoSession) The request does not have a session.
+//
+//   - (errTaggedRemoteSource) The source is remote (another node) and tagged.
+//     Users must use their own user-owned devices to manage other nodes'
+//     web clients.
+//
+//   - (errTaggedLocalSource) The source is local (the same node) and tagged.
+//     Tagged nodes can only be remotely managed, allowing ACLs to dictate
+//     access to web clients.
+//
+//   - (errNotOwner) The source is not the owner of this client (if the
+//     client is user-owned). Only the owner is allowed to manage the
+//     node via the web client.
+//
+// If no error is returned, the browserSession is always non-nil.
+// getTailscaleBrowserSession does not check whether the session has been
+// authorized by the user. Callers can use browserSession.isAuthorized.
+//
+// The WhoIsResponse is always populated, with a non-nil Node and UserProfile,
+// unless getTailscaleBrowserSession reports errNotUsingTailscale.
+func (s *Server) getSession(r *http.Request) (*browserSession, *apitype.WhoIsResponse, error) {
+	whoIs, whoIsErr := s.lc.WhoIs(r.Context(), r.RemoteAddr)
+	status, statusErr := s.lc.StatusWithoutPeers(r.Context())
+	switch {
+	case whoIsErr != nil:
+		return nil, nil, errNotUsingTailscale
+	case statusErr != nil:
+		return nil, whoIs, statusErr
+	case status.Self == nil:
+		return nil, whoIs, errors.New("missing self node in tailscale status")
+	case whoIs.Node.IsTagged() && whoIs.Node.StableID == status.Self.ID:
+		return nil, whoIs, errTaggedLocalSource
+	case whoIs.Node.IsTagged():
+		return nil, whoIs, errTaggedRemoteSource
+	case !status.Self.IsTagged() && status.Self.UserID != whoIs.UserProfile.ID:
+		return nil, whoIs, errNotOwner
+	}
+	srcNode := whoIs.Node.ID
+	srcUser := whoIs.UserProfile.ID
+
+	cookie, err := r.Cookie(sessionCookieName)
+	if errors.Is(err, http.ErrNoCookie) {
+		return nil, whoIs, errNoSession
+	} else if err != nil {
+		return nil, whoIs, err
+	}
+	v, ok := s.browserSessions.Load(cookie.Value)
+	if !ok {
+		return nil, whoIs, errNoSession
+	}
+	session := v.(*browserSession)
+	if session.SrcNode != srcNode || session.SrcUser != srcUser {
+		// In this case the browser cookie is associated with another tailscale node.
+		// Maybe the source browser's machine was logged out and then back in as a different node.
+		// Return errNoSession because there is no session for this user.
+		return nil, whoIs, errNoSession
+	} else if session.isExpired(s.timeNow()) {
+		// Session expired, remove from session map and return errNoSession.
+		s.browserSessions.Delete(session.ID)
+		return nil, whoIs, errNoSession
+	}
+	return session, whoIs, nil
+}
+
+// newSession creates a new session associated with the given source user/node,
+// and stores it back to the session cache. Creating of a new session includes
+// generating a new auth URL from the control server.
+func (s *Server) newSession(ctx context.Context, src *apitype.WhoIsResponse) (*browserSession, error) {
+	d, err := s.getOrAwaitAuth(ctx, "", src.Node.ID)
+	if err != nil {
+		return nil, err
+	}
+	sid, err := s.newSessionID()
+	if err != nil {
+		return nil, err
+	}
+	session := &browserSession{
+		ID:      sid,
+		SrcNode: src.Node.ID,
+		SrcUser: src.UserProfile.ID,
+		AuthID:  d.ID,
+		AuthURL: d.URL,
+		Created: s.timeNow(),
+	}
+	s.browserSessions.Store(sid, session)
+	return session, nil
+}
+
+// awaitUserAuth blocks until the given session auth has been completed
+// by the user on the control server, then updates the session cache upon
+// completion. An error is returned if control auth failed for any reason.
+func (s *Server) awaitUserAuth(ctx context.Context, session *browserSession) error {
+	if session.isAuthorized(s.timeNow()) {
+		return nil // already authorized
+	}
+	d, err := s.getOrAwaitAuth(ctx, session.AuthID, session.SrcNode)
+	if err != nil {
+		// Clean up the session. Doing this on any error from control
+		// server to avoid the user getting stuck with a bad session
+		// cookie.
+		s.browserSessions.Delete(session.ID)
+		return err
+	}
+	if d.Complete {
+		session.Authenticated = d.Complete
+		s.browserSessions.Store(session.ID, session)
+	}
+	return nil
+}
+
+// getOrAwaitAuth connects to the control server for user auth,
+// with the following behavior:
+//
+//  1. If authID is provided empty, a new auth URL is created on the control
+//     server and reported back here, which can then be used to redirect the
+//     user on the frontend.
+//  2. If authID is provided non-empty, the connection to control blocks until
+//     the user has completed authenticating the associated auth URL,
+//     or until ctx is canceled.
+func (s *Server) getOrAwaitAuth(ctx context.Context, authID string, src tailcfg.NodeID) (*tailcfg.WebClientAuthResponse, error) {
+	type data struct {
+		ID  string
+		Src tailcfg.NodeID
+	}
+	var b bytes.Buffer
+	if err := json.NewEncoder(&b).Encode(data{ID: authID, Src: src}); err != nil {
+		return nil, err
+	}
+	url := "http://" + apitype.LocalAPIHost + "/localapi/v0/debug-web-client"
+	req, err := http.NewRequestWithContext(ctx, "POST", url, &b)
+	if err != nil {
+		return nil, err
+	}
+	resp, err := s.lc.DoLocalRequest(req)
+	if err != nil {
+		return nil, err
+	}
+	body, _ := io.ReadAll(resp.Body)
+	resp.Body.Close()
+	if resp.StatusCode != http.StatusOK {
+		return nil, fmt.Errorf("failed request: %s", body)
+	}
+	var authResp *tailcfg.WebClientAuthResponse
+	if err := json.Unmarshal(body, &authResp); err != nil {
+		return nil, err
+	}
+	return authResp, nil
+}
+
+func (s *Server) newSessionID() (string, error) {
+	raw := make([]byte, 16)
+	for i := 0; i < 5; i++ {
+		if _, err := rand.Read(raw); err != nil {
+			return "", err
+		}
+		cookie := "ts-web-" + base64.RawURLEncoding.EncodeToString(raw)
+		if _, ok := s.browserSessions.Load(cookie); !ok {
+			return cookie, nil
+		}
+	}
+	return "", errors.New("too many collisions generating new session; please refresh page")
+}

client/web/package.json

@@ -18,7 +18,7 @@
     "@types/react-dom": "^18.0.6",
     "@vitejs/plugin-react-swc": "^3.3.2",
     "autoprefixer": "^10.4.15",
-    "postcss": "^8.4.27",
+    "postcss": "^8.4.31",
     "prettier": "^2.5.1",
     "prettier-plugin-organize-imports": "^3.2.2",
     "tailwindcss": "^3.3.3",

client/web/qnap.go

@@ -9,6 +9,7 @@ package web
 import (
 	"crypto/tls"
 	"encoding/xml"
+	"errors"
 	"fmt"
 	"io"
 	"log"
@@ -18,21 +19,17 @@ import (
 
 // authorizeQNAP authenticates the logged-in QNAP user and verifies that they
 // are authorized to use the web client.
-// It reports true if the request is authorized to continue, and false otherwise.
-// authorizeQNAP manages writing out any relevant authorization errors to the
-// ResponseWriter itself.
-func authorizeQNAP(w http.ResponseWriter, r *http.Request) (ok bool) {
+// If the user is not authorized to use the client, an error is returned.
+func authorizeQNAP(r *http.Request) (ar authResponse, err error) {
 	_, resp, err := qnapAuthn(r)
 	if err != nil {
-		http.Error(w, err.Error(), http.StatusUnauthorized)
-		return false
+		return ar, err
 	}
 	if resp.IsAdmin == 0 {
-		http.Error(w, "user is not an admin", http.StatusForbidden)
-		return false
+		return ar, errors.New("user is not an admin")
 	}
 
-	return true
+	return authResponse{OK: true}, nil
 }
 
 type qnapAuthResponse struct {

client/web/src/api.ts

@@ -1,4 +1,5 @@
 let csrfToken: string
+let synoToken: string | undefined // required for synology API requests
 let unraidCsrfToken: string | undefined // required for unraid POST requests (#8062)
 
 // apiFetch wraps the standard JS fetch function with csrf header
@@ -15,9 +16,13 @@ export function apiFetch(
 ): Promise<Response> {
   const urlParams = new URLSearchParams(window.location.search)
   const nextParams = new URLSearchParams(params)
-  const token = urlParams.get("SynoToken")
-  if (token) {
-    nextParams.set("SynoToken", token)
+  if (synoToken) {
+    nextParams.set("SynoToken", synoToken)
+  } else {
+    const token = urlParams.get("SynoToken")
+    if (token) {
+      nextParams.set("SynoToken", token)
+    }
   }
   const search = nextParams.toString()
   const url = `api${endpoint}${search ? `?${search}` : ""}`
@@ -62,6 +67,10 @@ function updateCsrfToken(r: Response) {
   }
 }
 
+export function setSynoToken(token?: string) {
+  synoToken = token
+}
+
 export function setUnraidCsrfToken(token?: string) {
   unraidCsrfToken = token
 }

client/web/src/components/app.tsx

@@ -1,124 +1,75 @@
+import cx from "classnames"
 import React from "react"
-import { Footer, Header, IP, State } from "src/components/legacy"
-import useNodeData, { NodeData } from "src/hooks/node-data"
-import { ReactComponent as ConnectedDeviceIcon } from "src/icons/connected-device.svg"
-import { ReactComponent as TailscaleIcon } from "src/icons/tailscale-icon.svg"
-import { ReactComponent as TailscaleLogo } from "src/icons/tailscale-logo.svg"
+import LegacyClientView from "src/components/views/legacy-client-view"
+import LoginClientView from "src/components/views/login-client-view"
+import ReadonlyClientView from "src/components/views/readonly-client-view"
+import useAuth, { AuthResponse, SessionsCallbacks } from "src/hooks/auth"
+import useNodeData from "src/hooks/node-data"
+import ManagementClientView from "./views/management-client-view"
 
 export default function App() {
-  // TODO(sonia): use isPosting value from useNodeData
-  // to fill loading states.
-  const { data, refreshData, updateNode } = useNodeData()
+  const { data: auth, loading: loadingAuth, sessions } = useAuth()
 
-  if (!data) {
-    // TODO(sonia): add a loading view
-    return <div className="text-center py-14">Loading...</div>
-  }
-
-  const needsLogin = data?.Status === "NeedsLogin" || data?.Status === "NoState"
-
-  return !needsLogin &&
-    (data.DebugMode === "login" || data.DebugMode === "full") ? (
-    <div className="flex flex-col items-center min-w-sm max-w-lg mx-auto py-10">
-      {data.DebugMode === "login" ? (
-        <LoginView {...data} />
+  return (
+    <div className="flex flex-col items-center min-w-sm max-w-lg mx-auto py-14">
+      {loadingAuth ? (
+        <div className="text-center py-14">Loading...</div> // TODO(sonia): add a loading view
       ) : (
-        <ManageView {...data} />
+        <WebClient auth={auth} sessions={sessions} />
       )}
-      <Footer className="mt-20" licensesURL={data.LicensesURL} />
-    </div>
-  ) : (
-    // Legacy client UI
-    <div className="py-14">
-      <main className="container max-w-lg mx-auto mb-8 py-6 px-8 bg-white rounded-md shadow-2xl">
-        <Header data={data} refreshData={refreshData} updateNode={updateNode} />
-        <IP data={data} />
-        <State data={data} updateNode={updateNode} />
-      </main>
-      <Footer licensesURL={data.LicensesURL} />
     </div>
   )
 }
 
-function LoginView(props: NodeData) {
+function WebClient({
+  auth,
+  sessions,
+}: {
+  auth?: AuthResponse
+  sessions: SessionsCallbacks
+}) {
+  const { data, refreshData, updateNode } = useNodeData()
+
   return (
     <>
-      <div className="pb-52 mx-auto">
-        <TailscaleLogo />
-      </div>
-      <div className="w-full p-4 bg-stone-50 rounded-3xl border border-gray-200 flex flex-col gap-4">
-        <div className="flex gap-2.5">
-          <ProfilePic url={props.Profile.ProfilePicURL} />
-          <div className="font-medium">
-            <div className="text-neutral-500 text-xs uppercase tracking-wide">
-              Owned by
-            </div>
-            <div className="text-neutral-800 text-sm leading-tight">
-              {/* TODO(sonia): support tagged node profile view more eloquently */}
-              {props.Profile.LoginName}
-            </div>
-          </div>
-        </div>
-        <div className="px-5 py-4 bg-white rounded-lg border border-gray-200 justify-between items-center flex">
-          <div className="flex gap-3">
-            <ConnectedDeviceIcon />
-            <div className="text-neutral-800">
-              <div className="text-lg font-medium leading-[25.20px]">
-                {props.DeviceName}
-              </div>
-              <div className="text-sm leading-tight">{props.IP}</div>
-            </div>
-          </div>
-          <button className="button button-blue ml-6">Access</button>
-        </div>
-      </div>
+      {!data ? (
+        <div className="text-center py-14">Loading...</div> // TODO(sonia): add a loading view
+      ) : data?.Status === "NeedsLogin" || data?.Status === "NoState" ? (
+        // Client not on a tailnet, render login.
+        <LoginClientView
+          data={data}
+          onLoginClick={() => updateNode({ Reauthenticate: true })}
+        />
+      ) : data.DebugMode === "full" && auth?.ok ? (
+        // Render new client interface in management mode.
+        <ManagementClientView {...data} />
+      ) : data.DebugMode === "login" || data.DebugMode === "full" ? (
+        // Render new client interface in readonly mode.
+        <ReadonlyClientView data={data} auth={auth} sessions={sessions} />
+      ) : (
+        // Render legacy client interface.
+        <LegacyClientView
+          data={data}
+          refreshData={refreshData}
+          updateNode={updateNode}
+        />
+      )}
+      {data && <Footer licensesURL={data.LicensesURL} />}
     </>
   )
 }
 
-function ManageView(props: NodeData) {
+export function Footer(props: { licensesURL: string; className?: string }) {
   return (
-    <div className="px-5">
-      <div className="flex justify-between mb-12">
-        <TailscaleIcon />
-        <div className="flex">
-          <p className="mr-2">{props.Profile.LoginName}</p>
-          {/* TODO(sonia): support tagged node profile view more eloquently */}
-          <ProfilePic url={props.Profile.ProfilePicURL} />
-        </div>
-      </div>
-      <p className="tracking-wide uppercase text-gray-600 pb-3">This device</p>
-      <div className="-mx-5 border rounded-md px-5 py-4 bg-white">
-        <div className="flex justify-between items-center text-lg">
-          <div className="flex items-center">
-            <ConnectedDeviceIcon />
-            <p className="font-medium ml-3">{props.DeviceName}</p>
-          </div>
-          <p className="tracking-widest">{props.IP}</p>
-        </div>
-      </div>
-      <p className="text-gray-500 pt-2">
-        Tailscale is up and running. You can connect to this device from devices
-        in your tailnet by using its name or IP address.
-      </p>
-    </div>
-  )
-}
-
-function ProfilePic({ url }: { url: string }) {
-  return (
-    <div className="relative flex-shrink-0 w-8 h-8 rounded-full overflow-hidden">
-      {url ? (
-        <div
-          className="w-8 h-8 flex pointer-events-none rounded-full bg-gray-200"
-          style={{
-            backgroundImage: `url(${url})`,
-            backgroundSize: "cover",
-          }}
-        />
-      ) : (
-        <div className="w-8 h-8 flex pointer-events-none rounded-full border border-gray-400 border-dashed" />
-      )}
-    </div>
+    <footer
+      className={cx("container max-w-lg mx-auto text-center", props.className)}
+    >
+      <a
+        className="text-xs text-gray-500 hover:text-gray-600"
+        href={props.licensesURL}
+      >
+        Open Source Licenses
+      </a>
+    </footer>
   )
 }

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

@@ -8,6 +8,52 @@ import { NodeData, NodeUpdate } from "src/hooks/node-data"
 // purely to ease migration to the new React-based web client, and will
 // eventually be completely removed.
 
+export default function LegacyClientView({
+  data,
+  refreshData,
+  updateNode,
+}: {
+  data: NodeData
+  refreshData: () => void
+  updateNode: (update: NodeUpdate) => void
+}) {
+  return (
+    <div className="container max-w-lg mx-auto mb-8 py-6 px-8 bg-white rounded-md shadow-2xl">
+      <Header data={data} refreshData={refreshData} updateNode={updateNode} />
+      <IP data={data} />
+      {data.Status === "NeedsMachineAuth" ? (
+        <div className="mb-4">
+          This device is authorized, but needs approval from a network admin
+          before it can connect to the network.
+        </div>
+      ) : (
+        <>
+          <div className="mb-4">
+            <p>
+              You are connected! Access this device over Tailscale using the
+              device name or IP address above.
+            </p>
+          </div>
+          <button
+            className={cx("button button-medium mb-4", {
+              "button-red": data.AdvertiseExitNode,
+              "button-blue": !data.AdvertiseExitNode,
+            })}
+            id="enabled"
+            onClick={() =>
+              updateNode({ AdvertiseExitNode: !data.AdvertiseExitNode })
+            }
+          >
+            {data.AdvertiseExitNode
+              ? "Stop advertising Exit Node"
+              : "Advertise as Exit Node"}
+          </button>
+        </>
+      )}
+    </div>
+  )
+}
+
 export function Header({
   data,
   refreshData,
@@ -184,115 +230,3 @@ export function IP(props: { data: NodeData }) {
     </>
   )
 }
-
-export function State({
-  data,
-  updateNode,
-}: {
-  data: NodeData
-  updateNode: (update: NodeUpdate) => void
-}) {
-  switch (data.Status) {
-    case "NeedsLogin":
-    case "NoState":
-      if (data.IP) {
-        return (
-          <>
-            <div className="mb-6">
-              <p className="text-gray-700">
-                Your device's key has expired. Reauthenticate this device by
-                logging in again, or{" "}
-                <a
-                  href="https://tailscale.com/kb/1028/key-expiry"
-                  className="link"
-                  target="_blank"
-                >
-                  learn more
-                </a>
-                .
-              </p>
-            </div>
-            <button
-              onClick={() => updateNode({ Reauthenticate: true })}
-              className="button button-blue w-full mb-4"
-            >
-              Reauthenticate
-            </button>
-          </>
-        )
-      } else {
-        return (
-          <>
-            <div className="mb-6">
-              <h3 className="text-3xl font-semibold mb-3">Log in</h3>
-              <p className="text-gray-700">
-                Get started by logging in to your Tailscale network.
-                Or,&nbsp;learn&nbsp;more at{" "}
-                <a
-                  href="https://tailscale.com/"
-                  className="link"
-                  target="_blank"
-                >
-                  tailscale.com
-                </a>
-                .
-              </p>
-            </div>
-            <button
-              onClick={() => updateNode({ Reauthenticate: true })}
-              className="button button-blue w-full mb-4"
-            >
-              Log In
-            </button>
-          </>
-        )
-      }
-    case "NeedsMachineAuth":
-      return (
-        <div className="mb-4">
-          This device is authorized, but needs approval from a network admin
-          before it can connect to the network.
-        </div>
-      )
-    default:
-      return (
-        <>
-          <div className="mb-4">
-            <p>
-              You are connected! Access this device over Tailscale using the
-              device name or IP address above.
-            </p>
-          </div>
-          <button
-            className={cx("button button-medium mb-4", {
-              "button-red": data.AdvertiseExitNode,
-              "button-blue": !data.AdvertiseExitNode,
-            })}
-            id="enabled"
-            onClick={() =>
-              updateNode({ AdvertiseExitNode: !data.AdvertiseExitNode })
-            }
-          >
-            {data.AdvertiseExitNode
-              ? "Stop advertising Exit Node"
-              : "Advertise as Exit Node"}
-          </button>
-        </>
-      )
-  }
-}
-
-export function Footer(props: { licensesURL: string; className?: string }) {
-  return (
-    <footer
-      className={cx("container max-w-lg mx-auto text-center", props.className)}
-    >
-      <a
-        className="text-xs text-gray-500 hover:text-gray-600"
-        href={props.licensesURL}
-      >
-        Open Source Licenses
-      </a>
-    </footer>
-  )
-}

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

@@ -0,0 +1,65 @@
+import React from "react"
+import { NodeData } from "src/hooks/node-data"
+import { ReactComponent as TailscaleIcon } from "src/icons/tailscale-icon.svg"
+
+/**
+ * LoginClientView is rendered when the client is not authenticated
+ * to a tailnet.
+ */
+export default function LoginClientView({
+  data,
+  onLoginClick,
+}: {
+  data: NodeData
+  onLoginClick: () => void
+}) {
+  return (
+    <div className="mb-8 py-6 px-8 bg-white rounded-md shadow-2xl">
+      <TailscaleIcon className="my-2 mb-8" />
+      {data.IP ? (
+        <>
+          <div className="mb-6">
+            <p className="text-gray-700">
+              Your device's key has expired. Reauthenticate this device by
+              logging in again, or{" "}
+              <a
+                href="https://tailscale.com/kb/1028/key-expiry"
+                className="link"
+                target="_blank"
+              >
+                learn more
+              </a>
+              .
+            </p>
+          </div>
+          <button
+            onClick={onLoginClick}
+            className="button button-blue w-full mb-4"
+          >
+            Reauthenticate
+          </button>
+        </>
+      ) : (
+        <>
+          <div className="mb-6">
+            <h3 className="text-3xl font-semibold mb-3">Log in</h3>
+            <p className="text-gray-700">
+              Get started by logging in to your Tailscale network.
+              Or,&nbsp;learn&nbsp;more at{" "}
+              <a href="https://tailscale.com/" className="link" target="_blank">
+                tailscale.com
+              </a>
+              .
+            </p>
+          </div>
+          <button
+            onClick={onLoginClick}
+            className="button button-blue w-full mb-4"
+          >
+            Log In
+          </button>
+        </>
+      )}
+    </div>
+  )
+}

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

@@ -0,0 +1,35 @@
+import React from "react"
+import { NodeData } from "src/hooks/node-data"
+import { ReactComponent as ConnectedDeviceIcon } from "src/icons/connected-device.svg"
+import { ReactComponent as TailscaleIcon } from "src/icons/tailscale-icon.svg"
+import ProfilePic from "src/ui/profile-pic"
+
+export default function ManagementClientView(props: NodeData) {
+  return (
+    <div className="px-5 mb-12">
+      <div className="flex justify-between mb-12">
+        <TailscaleIcon />
+        <div className="flex">
+          <p className="mr-2">{props.Profile.LoginName}</p>
+          {/* TODO(sonia): support tagged node profile view more eloquently */}
+          <ProfilePic url={props.Profile.ProfilePicURL} />
+        </div>
+      </div>
+      <p className="tracking-wide uppercase text-gray-600 pb-3">This device</p>
+      <div className="-mx-5 border rounded-md px-5 py-4 bg-white">
+        <div className="flex justify-between items-center text-lg">
+          <div className="flex items-center">
+            <ConnectedDeviceIcon />
+            <p className="font-medium ml-3">{props.DeviceName}</p>
+          </div>
+          <p className="tracking-widest">{props.IP}</p>
+        </div>
+      </div>
+      <p className="text-gray-500 pt-2">
+        Tailscale is up and running. You can connect to this device from devices
+        in your tailnet by using its name or IP address.
+      </p>
+      <button className="button button-blue mt-6">Advertise exit node</button>
+    </div>
+  )
+}

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

@@ -0,0 +1,71 @@
+import React from "react"
+import { AuthResponse, AuthType, SessionsCallbacks } from "src/hooks/auth"
+import { NodeData } from "src/hooks/node-data"
+import { ReactComponent as ConnectedDeviceIcon } from "src/icons/connected-device.svg"
+import { ReactComponent as TailscaleLogo } from "src/icons/tailscale-logo.svg"
+import ProfilePic from "src/ui/profile-pic"
+
+/**
+ * ReadonlyClientView is rendered when the web interface is either
+ *
+ * 1. being viewed by a user not allowed to manage the node
+ *    (e.g. user does not own the node)
+ *
+ * 2. or the user is allowed to manage the node but does not
+ *    yet have a valid browser session.
+ */
+export default function ReadonlyClientView({
+  data,
+  auth,
+  sessions,
+}: {
+  data: NodeData
+  auth?: AuthResponse
+  sessions: SessionsCallbacks
+}) {
+  return (
+    <>
+      <div className="pb-52 mx-auto">
+        <TailscaleLogo />
+      </div>
+      <div className="w-full p-4 bg-stone-50 rounded-3xl border border-gray-200 flex flex-col gap-4">
+        <div className="flex gap-2.5">
+          <ProfilePic url={data.Profile.ProfilePicURL} />
+          <div className="font-medium">
+            <div className="text-neutral-500 text-xs uppercase tracking-wide">
+              Managed by
+            </div>
+            <div className="text-neutral-800 text-sm leading-tight">
+              {/* TODO(sonia): support tagged node profile view more eloquently */}
+              {data.Profile.LoginName}
+            </div>
+          </div>
+        </div>
+        <div className="px-5 py-4 bg-white rounded-lg border border-gray-200 justify-between items-center flex">
+          <div className="flex gap-3">
+            <ConnectedDeviceIcon />
+            <div className="text-neutral-800">
+              <div className="text-lg font-medium leading-[25.20px]">
+                {data.DeviceName}
+              </div>
+              <div className="text-sm leading-tight">{data.IP}</div>
+            </div>
+          </div>
+          {auth?.authNeeded == AuthType.tailscale && (
+            <button
+              className="button button-blue ml-6"
+              onClick={() => {
+                sessions
+                  .new()
+                  .then((url) => window.open(url, "_blank"))
+                  .then(() => sessions.wait())
+              }}
+            >
+              Access
+            </button>
+          )}
+        </div>
+      </div>
+    </>
+  )
+}

client/web/src/hooks/auth.ts

@@ -0,0 +1,79 @@
+import { useCallback, useEffect, useState } from "react"
+import { apiFetch, setSynoToken } from "src/api"
+
+export enum AuthType {
+  synology = "synology",
+  tailscale = "tailscale",
+}
+
+export type AuthResponse = {
+  ok: boolean
+  authNeeded?: AuthType
+}
+
+export type SessionsCallbacks = {
+  new: () => Promise<string> // creates new auth session and returns authURL
+  wait: () => Promise<void> // blocks until auth is completed
+}
+
+// useAuth reports and refreshes Tailscale auth status
+// for the web client.
+export default function useAuth() {
+  const [data, setData] = useState<AuthResponse>()
+  const [loading, setLoading] = useState<boolean>(true)
+
+  const loadAuth = useCallback(() => {
+    setLoading(true)
+    return apiFetch("/auth", "GET")
+      .then((r) => r.json())
+      .then((d) => {
+        setData(d)
+        switch ((d as AuthResponse).authNeeded) {
+          case AuthType.synology:
+            fetch("/webman/login.cgi")
+              .then((r) => r.json())
+              .then((a) => {
+                setSynoToken(a.SynoToken)
+                setLoading(false)
+              })
+            break
+          default:
+            setLoading(false)
+        }
+      })
+      .catch((error) => {
+        setLoading(false)
+        console.error(error)
+      })
+  }, [])
+
+  const newSession = useCallback(() => {
+    return apiFetch("/auth/session/new", "GET")
+      .then((r) => r.json())
+      .then((d) => d.authUrl)
+      .catch((error) => {
+        console.error(error)
+      })
+  }, [])
+
+  const waitForSessionCompletion = useCallback(() => {
+    return apiFetch("/auth/session/wait", "GET")
+      .then(() => loadAuth()) // refresh auth data
+      .catch((error) => {
+        console.error(error)
+      })
+  }, [])
+
+  useEffect(() => {
+    loadAuth()
+  }, [])
+
+  return {
+    data,
+    loading,
+    sessions: {
+      new: newSession,
+      wait: waitForSessionCompletion,
+    },
+  }
+}

client/web/src/ui/profile-pic.tsx

@@ -0,0 +1,19 @@
+import React from "react"
+
+export default function ProfilePic({ url }: { url: string }) {
+  return (
+    <div className="relative flex-shrink-0 w-8 h-8 rounded-full overflow-hidden">
+      {url ? (
+        <div
+          className="w-8 h-8 flex pointer-events-none rounded-full bg-gray-200"
+          style={{
+            backgroundImage: `url(${url})`,
+            backgroundSize: "cover",
+          }}
+        />
+      ) : (
+        <div className="w-8 h-8 flex pointer-events-none rounded-full border border-gray-400 border-dashed" />
+      )}
+    </div>
+  )
+}

client/web/synology.go

@@ -7,6 +7,7 @@
 package web
 
 import (
+	"errors"
 	"fmt"
 	"net/http"
 	"os/exec"
@@ -17,62 +18,44 @@ import (
 
 // authorizeSynology authenticates the logged-in Synology user and verifies
 // that they are authorized to use the web client.
-// It reports true if the request is authorized to continue, and false otherwise.
-// authorizeSynology manages writing out any relevant authorization errors to the
-// ResponseWriter itself.
-func authorizeSynology(w http.ResponseWriter, r *http.Request) (ok bool) {
-	if synoTokenRedirect(w, r) {
-		return false
+// The returned authResponse indicates if the user is authorized,
+// and if additional steps are needed to authenticate the user.
+// If the user is authenticated, but not authorized to use the client, an error is returned.
+func authorizeSynology(r *http.Request) (resp authResponse, err error) {
+	if !hasSynoToken(r) {
+		return authResponse{OK: false, AuthNeeded: synoAuth}, nil
 	}
 
 	// authenticate the Synology user
 	cmd := exec.Command("/usr/syno/synoman/webman/modules/authenticate.cgi")
 	out, err := cmd.CombinedOutput()
 	if err != nil {
-		http.Error(w, fmt.Sprintf("auth: %v: %s", err, out), http.StatusUnauthorized)
-		return false
+		return resp, fmt.Errorf("auth: %v: %s", err, out)
 	}
 	user := strings.TrimSpace(string(out))
 
 	// check if the user is in the administrators group
 	isAdmin, err := groupmember.IsMemberOfGroup("administrators", user)
 	if err != nil {
-		http.Error(w, err.Error(), http.StatusForbidden)
-		return false
+		return resp, err
 	}
 	if !isAdmin {
-		http.Error(w, "not a member of administrators group", http.StatusForbidden)
-		return false
+		return resp, errors.New("not a member of administrators group")
 	}
 
-	return true
+	return authResponse{OK: true}, nil
 }
 
-func synoTokenRedirect(w http.ResponseWriter, r *http.Request) bool {
+// hasSynoToken returns true if the request include a SynoToken used for synology auth.
+func hasSynoToken(r *http.Request) bool {
 	if r.Header.Get("X-Syno-Token") != "" {
-		return false
+		return true
 	}
 	if r.URL.Query().Get("SynoToken") != "" {
-		return false
+		return true
 	}
 	if r.Method == "POST" && r.FormValue("SynoToken") != "" {
-		return false
+		return true
 	}
-	// We need a SynoToken for authenticate.cgi.
-	// So we tell the client to get one.
-	_, _ = fmt.Fprint(w, synoTokenRedirectHTML)
-	return true
+	return false
 }
-
-const synoTokenRedirectHTML = `<html>
-Redirecting with session token...
-<script>
-  fetch("/webman/login.cgi")
-    .then(r => r.json())
-    .then(data => {
-	u = new URL(window.location)
-	u.searchParams.set("SynoToken", data.SynoToken)
-	document.location = u
-    })
-</script>
-`

client/web/web.go

@@ -29,23 +29,35 @@ import (
 	"tailscale.com/ipn/ipnstate"
 	"tailscale.com/licenses"
 	"tailscale.com/net/netutil"
+	"tailscale.com/net/tsaddr"
 	"tailscale.com/tailcfg"
+	"tailscale.com/types/logger"
 	"tailscale.com/util/httpm"
 	"tailscale.com/version/distro"
 )
 
+// ListenPort is the static port used for the web client when run inside tailscaled.
+// (5252 are the numbers above the letters "TSTS" on a qwerty keyboard.)
+const ListenPort = 5252
+
 // Server is the backend server for a Tailscale web client.
 type Server struct {
-	lc *tailscale.LocalClient
+	mode ServerMode
 
-	devMode     bool
-	tsDebugMode string
+	logf    logger.Logf
+	lc      *tailscale.LocalClient
+	timeNow func() time.Time
 
+	// devMode indicates that the server run with frontend assets
+	// served by a Vite dev server, allowing for local development
+	// on the web client frontend.
+	devMode    bool
 	cgiMode    bool
 	pathPrefix string
 
-	assetsHandler http.Handler // serves frontend assets
 	apiHandler    http.Handler // serves api endpoints; csrf-protected
+	assetsHandler http.Handler // serves frontend assets
+	assetsCleanup func()       // called from Server.Shutdown
 
 	// browserSessions is an in-memory cache of browser sessions for the
 	// full management web client, which is only accessible over Tailscale.
@@ -61,57 +73,40 @@ type Server struct {
 	browserSessions sync.Map
 }
 
+// ServerMode specifies the mode of a running web.Server.
+type ServerMode string
+
 const (
-	sessionCookieName   = "TS-Web-Session"
-	sessionCookieExpiry = time.Hour * 24 * 30 // 30 days
+	// LoginServerMode serves a readonly login client for logging a
+	// node into a tailnet, and viewing a readonly interface of the
+	// node's current Tailscale settings.
+	//
+	// In this mode, API calls are authenticated via platform auth.
+	LoginServerMode ServerMode = "login"
+
+	// ManageServerMode serves a management client for editing tailscale
+	// settings of a node.
+	//
+	// 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.
+	ManageServerMode ServerMode = "manage"
+
+	// LegacyServerMode serves the legacy web client, visible to users
+	// prior to release of tailscale/corp#14335.
+	LegacyServerMode ServerMode = "legacy"
 )
 
-// browserSession holds data about a user's browser session
-// on the full management web client.
-type browserSession struct {
-	// ID is the unique identifier for the session.
-	// It is passed in the user's "TS-Web-Session" browser cookie.
-	ID            string
-	SrcNode       tailcfg.StableNodeID
-	SrcUser       tailcfg.UserID
-	AuthURL       string    // control server URL for user to authenticate the session
-	Authenticated time.Time // when zero, authentication not complete
-}
-
-// isAuthorized reports true if the given session is authorized
-// to be used by its associated user to access the full management
-// web client.
-//
-// isAuthorized is true only when s.Authenticated is non-zero
-// (i.e. the user has authenticated the session) and the session
-// is not expired.
-// 2023-10-05: Sessions expire by default after 30 days.
-func (s *browserSession) isAuthorized() bool {
-	switch {
-	case s == nil:
-		return false
-	case s.Authenticated.IsZero():
-		return false // awaiting auth
-	case s.isExpired(): // TODO: add time field to server?
-		return false // expired
-	}
-	return true
-}
-
-// isExpired reports true if s is expired.
-// 2023-10-05: Sessions expire by default after 30 days.
-// If s.Authenticated is zero, isExpired reports false.
-func (s *browserSession) isExpired() bool {
-	return !s.Authenticated.IsZero() && s.Authenticated.Before(time.Now().Add(-sessionCookieExpiry)) // TODO: add time field to server?
-}
+var (
+	exitNodeRouteV4 = netip.MustParsePrefix("0.0.0.0/0")
+	exitNodeRouteV6 = netip.MustParsePrefix("::/0")
+)
 
 // ServerOpts contains options for constructing a new Server.
 type ServerOpts struct {
-	DevMode bool
-
-	// LoginOnly indicates that the server should only serve the minimal
-	// login client and not the full web client.
-	LoginOnly bool
+	// Mode specifies the mode of web client being constructed.
+	Mode ServerMode
 
 	// CGIMode indicates if the server is running as a CGI script.
 	CGIMode bool
@@ -122,21 +117,50 @@ type ServerOpts struct {
 	// LocalClient is the tailscale.LocalClient to use for this web server.
 	// If nil, a new one will be created.
 	LocalClient *tailscale.LocalClient
+
+	// TimeNow optionally provides a time function.
+	// time.Now is used as default.
+	TimeNow func() time.Time
+
+	// Logf optionally provides a logger function.
+	// log.Printf is used as default.
+	Logf logger.Logf
 }
 
 // NewServer constructs a new Tailscale web client server.
-// The provided context should live for the duration of the Server's lifetime.
-func NewServer(ctx context.Context, opts ServerOpts) (s *Server, cleanup func()) {
+// If err is empty, s is always non-nil.
+// ctx is only required to live the duration of the NewServer call,
+// and not the lifespan of the web server.
+func NewServer(opts ServerOpts) (s *Server, err error) {
+	switch opts.Mode {
+	case LoginServerMode, ManageServerMode, LegacyServerMode:
+		// valid types
+	case "":
+		return nil, fmt.Errorf("must specify a Mode")
+	default:
+		return nil, fmt.Errorf("invalid Mode provided")
+	}
 	if opts.LocalClient == nil {
 		opts.LocalClient = &tailscale.LocalClient{}
 	}
 	s = &Server{
-		devMode:    opts.DevMode,
+		mode:       opts.Mode,
+		logf:       opts.Logf,
+		devMode:    envknob.Bool("TS_DEBUG_WEB_CLIENT_DEV"),
 		lc:         opts.LocalClient,
+		cgiMode:    opts.CGIMode,
 		pathPrefix: opts.PathPrefix,
+		timeNow:    opts.TimeNow,
 	}
-	s.tsDebugMode = s.debugMode()
-	s.assetsHandler, cleanup = assetsHandler(opts.DevMode)
+	if s.timeNow == nil {
+		s.timeNow = time.Now
+	}
+	if s.logf == nil {
+		s.logf = log.Printf
+	}
+	s.assetsHandler, s.assetsCleanup = assetsHandler(s.devMode)
+
+	var metric string // clientmetric to report on startup
 
 	// Create handler for "/api" requests with CSRF protection.
 	// We don't require secure cookies, since the web client is regularly used
@@ -144,31 +168,30 @@ func NewServer(ctx context.Context, opts ServerOpts) (s *Server, cleanup func())
 	// 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))
-	if s.tsDebugMode == "login" {
-		// For the login client, we don't serve the full web client API,
-		// only the login endpoints.
+	if s.mode == LoginServerMode {
 		s.apiHandler = csrfProtect(http.HandlerFunc(s.serveLoginAPI))
-		s.lc.IncrementCounter(context.Background(), "web_login_client_initialization", 1)
+		metric = "web_login_client_initialization"
 	} else {
 		s.apiHandler = csrfProtect(http.HandlerFunc(s.serveAPI))
-		s.lc.IncrementCounter(context.Background(), "web_client_initialization", 1)
+		metric = "web_client_initialization"
 	}
 
-	return s, cleanup
+	// Don't block startup on reporting metric.
+	// Report in separate go routine with 5 second timeout.
+	go func() {
+		ctx, cancel := context.WithTimeout(context.Background(), 5*time.Second)
+		defer cancel()
+		s.lc.IncrementCounter(ctx, metric, 1)
+	}()
+
+	return s, nil
 }
 
-// debugMode returns the debug mode the web client is being run in.
-// The empty string is returned in the case that this instance is
-// not running in any debug mode.
-func (s *Server) debugMode() string {
-	if !s.devMode {
-		return "" // debug modes only available in dev
+func (s *Server) Shutdown() {
+	s.logf("web.Server: shutting down")
+	if s.assetsCleanup != nil {
+		s.assetsCleanup()
 	}
-	switch mode := os.Getenv("TS_DEBUG_WEB_CLIENT_MODE"); mode {
-	case "login", "full": // valid debug modes
-		return mode
-	}
-	return ""
 }
 
 // ServeHTTP processes all requests for the Tailscale web client.
@@ -184,42 +207,142 @@ func (s *Server) ServeHTTP(w http.ResponseWriter, r *http.Request) {
 }
 
 func (s *Server) serve(w http.ResponseWriter, r *http.Request) {
+	if s.mode == ManageServerMode {
+		// In manage mode, requests must be sent directly to the bare Tailscale IP address.
+		// If a request comes in on any other hostname, redirect.
+		if s.requireTailscaleIP(w, r) {
+			return // user was redirected
+		}
+
+		// serve HTTP 204 on /ok requests as connectivity check
+		if r.Method == httpm.GET && r.URL.Path == "/ok" {
+			w.WriteHeader(http.StatusNoContent)
+			return
+		}
+
+		if !s.devMode {
+			w.Header().Set("X-Frame-Options", "DENY")
+			// TODO: use CSP nonce or hash to eliminate need for unsafe-inline
+			w.Header().Set("Content-Security-Policy", "default-src 'self' 'unsafe-inline'; img-src * data:")
+			w.Header().Set("Cross-Origin-Resource-Policy", "same-origin")
+		}
+	}
+
 	if strings.HasPrefix(r.URL.Path, "/api/") {
+		switch {
+		case r.URL.Path == "/api/auth" && r.Method == httpm.GET:
+			s.serveAPIAuth(w, r) // serve auth status
+			return
+		case r.URL.Path == "/api/auth/session/new" && r.Method == httpm.GET:
+			s.serveAPIAuthSessionNew(w, r) // create new session
+			return
+		case r.URL.Path == "/api/auth/session/wait" && r.Method == httpm.GET:
+			s.serveAPIAuthSessionWait(w, r) // wait for session to be authorized
+			return
+		}
+		if ok := s.authorizeRequest(w, r); !ok {
+			http.Error(w, "not authorized", http.StatusUnauthorized)
+			return
+		}
 		// Pass API requests through to the API handler.
 		s.apiHandler.ServeHTTP(w, r)
 		return
 	}
 	if !s.devMode {
-		s.lc.IncrementCounter(context.Background(), "web_client_page_load", 1)
+		s.lc.IncrementCounter(r.Context(), "web_client_page_load", 1)
 	}
 	s.assetsHandler.ServeHTTP(w, r)
 }
 
-// authorizePlatformRequest reports whether the request from the web client
-// is authorized to access the client for those platforms that support it.
+// requireTailscaleIP redirects an incoming request if the HTTP request was not made to a bare Tailscale IP address.
+// The request will be redirected to the Tailscale IP, port 5252, with the original request path.
+// This allows any custom hostname to be used to access the device, but protects against DNS rebinding attacks.
+// Returns true if the request has been fully handled, either be returning a redirect or an HTTP error.
+func (s *Server) requireTailscaleIP(w http.ResponseWriter, r *http.Request) (handled bool) {
+	const (
+		ipv4ServiceHost = tsaddr.TailscaleServiceIPString
+		ipv6ServiceHost = "[" + tsaddr.TailscaleServiceIPv6String + "]"
+	)
+	// allow requests on quad-100 (or ipv6 equivalent)
+	if r.Host == ipv4ServiceHost || r.Host == ipv6ServiceHost {
+		return false
+	}
+
+	st, err := s.lc.StatusWithoutPeers(r.Context())
+	if err != nil {
+		s.logf("error getting status: %v", err)
+		http.Error(w, "internal error", http.StatusInternalServerError)
+		return true
+	}
+
+	var ipv4 string // store the first IPv4 address we see for redirect later
+	for _, ip := range st.Self.TailscaleIPs {
+		if ip.Is4() {
+			if r.Host == fmt.Sprintf("%s:%d", ip, ListenPort) {
+				return false
+			}
+			ipv4 = ip.String()
+		}
+		if ip.Is6() && r.Host == fmt.Sprintf("[%s]:%d", ip, ListenPort) {
+			return false
+		}
+	}
+	newURL := *r.URL
+	newURL.Host = fmt.Sprintf("%s:%d", ipv4, ListenPort)
+	http.Redirect(w, r, newURL.String(), http.StatusMovedPermanently)
+	return true
+}
+
+// authorizeRequest reports whether the request from the web client
+// is authorized to be completed.
 // It reports true if the request is authorized, and false otherwise.
-// authorizePlatformRequest manages writing out any relevant authorization
+// authorizeRequest manages writing out any relevant authorization
 // errors to the ResponseWriter itself.
-func authorizePlatformRequest(w http.ResponseWriter, r *http.Request) (ok bool) {
+func (s *Server) authorizeRequest(w http.ResponseWriter, r *http.Request) (ok bool) {
+	if s.mode == ManageServerMode { // client using tailscale auth
+		_, err := s.lc.WhoIs(r.Context(), r.RemoteAddr)
+		switch {
+		case err != nil:
+			// All requests must be made over tailscale.
+			http.Error(w, "must access over tailscale", http.StatusUnauthorized)
+			return false
+		case r.URL.Path == "/api/data" && r.Method == httpm.GET:
+			// Readonly endpoint allowed without browser session.
+			return true
+		case strings.HasPrefix(r.URL.Path, "/api/"):
+			// All other /api/ endpoints require a valid browser session.
+			//
+			// TODO(sonia): s.getSession calls whois again,
+			// should try and use the above call instead of running another
+			// localapi request.
+			session, _, err := s.getSession(r)
+			if err != nil || !session.isAuthorized(s.timeNow()) {
+				http.Error(w, "no valid session", http.StatusUnauthorized)
+				return false
+			}
+			return true
+		default:
+			// No additional auth on non-api (assets, index.html, etc).
+			return true
+		}
+	}
+	// Client using system-specific auth.
 	switch distro.Get() {
 	case distro.Synology:
-		return authorizeSynology(w, r)
+		resp, _ := authorizeSynology(r)
+		return resp.OK
 	case distro.QNAP:
-		return authorizeQNAP(w, r)
+		resp, _ := authorizeQNAP(r)
+		return resp.OK
+	default:
+		return true // no additional auth for this distro
 	}
-	return true
 }
 
 // serveLoginAPI serves requests for the web login client.
 // It should only be called by Server.ServeHTTP, via Server.apiHandler,
 // which protects the handler using gorilla csrf.
 func (s *Server) serveLoginAPI(w http.ResponseWriter, r *http.Request) {
-	// The login client is run directly from client plugins,
-	// so first authenticate and authorize the request for the host platform.
-	if ok := authorizePlatformRequest(w, r); !ok {
-		return
-	}
-
 	w.Header().Set("X-CSRF-Token", csrf.Token(r))
 	if r.URL.Path != "/api/data" { // only endpoint allowed for login client
 		http.Error(w, "invalid endpoint", http.StatusNotFound)
@@ -229,141 +352,123 @@ func (s *Server) serveLoginAPI(w http.ResponseWriter, r *http.Request) {
 	case httpm.GET:
 		// TODO(soniaappasamy): we may want a minimal node data response here
 		s.serveGetNodeData(w, r)
-	case httpm.POST:
-		// TODO(soniaappasamy): implement
-	default:
-		http.Error(w, "method not allowed", http.StatusMethodNotAllowed)
+		return
 	}
+	http.Error(w, "invalid endpoint", http.StatusNotFound)
 	return
 }
 
+type authType string
+
 var (
-	errNoSession         = errors.New("no-browser-session")
-	errNotUsingTailscale = errors.New("not-using-tailscale")
-	errTaggedSource      = errors.New("tagged-source")
-	errNotOwner          = errors.New("not-owner")
+	synoAuth      authType = "synology"  // user needs a SynoToken for subsequent API calls
+	tailscaleAuth authType = "tailscale" // user needs to complete Tailscale check mode
 )
 
-// getTailscaleBrowserSession retrieves the browser session associated with
-// the request, if one exists.
-//
-// An error is returned in any of the following cases:
-//
-//   - (errNotUsingTailscale) The request was not made over tailscale.
-//
-//   - (errNoSession) The request does not have a session.
-//
-//   - (errTaggedSource) The source is a tagged node. Users must use their
-//     own user-owned devices to manage other nodes' web clients.
-//
-//   - (errNotOwner) The source is not the owner of this client (if the
-//     client is user-owned). Only the owner is allowed to manage the
-//     node via the web client.
-//
-// If no error is returned, the browserSession is always non-nil.
-// getTailscaleBrowserSession does not check whether the session has been
-// authorized by the user. Callers can use browserSession.isAuthorized.
-func (s *Server) getTailscaleBrowserSession(r *http.Request) (*browserSession, error) {
-	whoIs, err := s.lc.WhoIs(r.Context(), r.RemoteAddr)
-	switch {
-	case err != nil:
-		return nil, errNotUsingTailscale
-	case whoIs.Node.IsTagged():
-		return nil, errTaggedSource
-	}
-	srcNode := whoIs.Node.StableID
-	srcUser := whoIs.UserProfile.ID
-
-	status, err := s.lc.StatusWithoutPeers(r.Context())
-	switch {
-	case err != nil:
-		return nil, err
-	case status.Self == nil:
-		return nil, errors.New("missing self node in tailscale status")
-	case !status.Self.IsTagged() && status.Self.UserID != srcUser:
-		return nil, errNotOwner
-	}
-
-	cookie, err := r.Cookie(sessionCookieName)
-	if errors.Is(err, http.ErrNoCookie) {
-		return nil, errNoSession
-	} else if err != nil {
-		return nil, err
-	}
-	v, ok := s.browserSessions.Load(cookie.Value)
-	if !ok {
-		return nil, errNoSession
-	}
-	session := v.(*browserSession)
-	if session.SrcNode != srcNode || session.SrcUser != srcUser {
-		// In this case the browser cookie is associated with another tailscale node.
-		// Maybe the source browser's machine was logged out and then back in as a different node.
-		// Return errNoSession because there is no session for this user.
-		return nil, errNoSession
-	} else if session.isExpired() {
-		// Session expired, remove from session map and return errNoSession.
-		s.browserSessions.Delete(session.ID)
-		return nil, errNoSession
-	}
-	return session, nil
-}
-
 type authResponse struct {
-	OK      bool   `json:"ok"`                // true when user has valid auth session
-	AuthURL string `json:"authUrl,omitempty"` // filled when user has control auth action to take
-	Error   string `json:"error,omitempty"`   // filled when Ok is false
+	OK         bool     `json:"ok"`                   // true when user has valid auth session
+	AuthNeeded authType `json:"authNeeded,omitempty"` // filled when user needs to complete a specific type of auth
 }
 
-func (s *Server) serveTailscaleAuth(w http.ResponseWriter, r *http.Request) {
+// serverAPIAuth handles requests to the /api/auth endpoint
+// and returns an authResponse indicating the current auth state and any steps the user needs to take.
+func (s *Server) serveAPIAuth(w http.ResponseWriter, r *http.Request) {
 	var resp authResponse
 
-	session, err := s.getTailscaleBrowserSession(r)
+	session, _, err := s.getSession(r)
 	switch {
+	case err != nil && errors.Is(err, errNotUsingTailscale):
+		// not using tailscale, so perform platform auth
+		switch distro.Get() {
+		case distro.Synology:
+			resp, err = authorizeSynology(r)
+			if err != nil {
+				http.Error(w, err.Error(), http.StatusUnauthorized)
+				return
+			}
+		case distro.QNAP:
+			resp, err = authorizeQNAP(r)
+			if err != nil {
+				http.Error(w, err.Error(), http.StatusUnauthorized)
+				return
+			}
+		default:
+			resp.OK = true // no additional auth for this distro
+		}
+	case err != nil && (errors.Is(err, errNotOwner) ||
+		errors.Is(err, errNotUsingTailscale) ||
+		errors.Is(err, errTaggedLocalSource) ||
+		errors.Is(err, errTaggedRemoteSource)):
+		// These cases are all restricted to the readonly view.
+		// No auth action to take.
+		resp = authResponse{OK: false}
 	case err != nil && !errors.Is(err, errNoSession):
-		resp = authResponse{OK: false, Error: err.Error()}
-	case session == nil:
-		// TODO(tailscale/corp#14335): Create a new auth path from control,
-		// and store back to s.browserSessions and request cookie.
-	case !session.isAuthorized():
-		// TODO(tailscale/corp#14335): Check on the session auth path status from control,
-		// and store back to s.browserSessions.
-	default:
-		resp = authResponse{OK: true}
-	}
-
-	if err := json.NewEncoder(w).Encode(resp); err != nil {
+		// Any other error.
 		http.Error(w, err.Error(), http.StatusInternalServerError)
 		return
+	case session.isAuthorized(s.timeNow()):
+		resp = authResponse{OK: true}
+	default:
+		resp = authResponse{OK: false, AuthNeeded: tailscaleAuth}
+	}
+
+	writeJSON(w, resp)
+}
+
+type newSessionAuthResponse struct {
+	AuthURL string `json:"authUrl,omitempty"`
+}
+
+// serveAPIAuthSessionNew handles requests to the /api/auth/session/new endpoint.
+func (s *Server) serveAPIAuthSessionNew(w http.ResponseWriter, r *http.Request) {
+	session, whois, err := s.getSession(r)
+	if err != nil && !errors.Is(err, errNoSession) {
+		// Source associated with request not allowed to create
+		// a session for this web client.
+		http.Error(w, err.Error(), http.StatusUnauthorized)
+		return
+	}
+	if session == nil {
+		// Create a new session.
+		// If one already existed, we return that authURL rather than creating a new one.
+		session, err = s.newSession(r.Context(), whois)
+		if err != nil {
+			http.Error(w, err.Error(), http.StatusInternalServerError)
+			return
+		}
+		// Set the cookie on browser.
+		http.SetCookie(w, &http.Cookie{
+			Name:    sessionCookieName,
+			Value:   session.ID,
+			Raw:     session.ID,
+			Path:    "/",
+			Expires: session.expires(),
+		})
+	}
+
+	writeJSON(w, newSessionAuthResponse{AuthURL: session.AuthURL})
+}
+
+// serveAPIAuthSessionWait handles requests to the /api/auth/session/wait endpoint.
+func (s *Server) serveAPIAuthSessionWait(w http.ResponseWriter, r *http.Request) {
+	session, _, err := s.getSession(r)
+	if err != nil {
+		http.Error(w, err.Error(), http.StatusUnauthorized)
+		return
+	}
+	if session.isAuthorized(s.timeNow()) {
+		return // already authorized
+	}
+	if err := s.awaitUserAuth(r.Context(), session); err != nil {
+		http.Error(w, err.Error(), http.StatusUnauthorized)
+		return
 	}
-	w.Header().Set("Content-Type", "application/json")
 }
 
 // serveAPI serves requests for the web client api.
 // It should only be called by Server.ServeHTTP, via Server.apiHandler,
 // which protects the handler using gorilla csrf.
 func (s *Server) serveAPI(w http.ResponseWriter, r *http.Request) {
-	if s.tsDebugMode == "full" {
-		// tailscale/corp#14335: Only restrict to tailscale auth in debug "full" web client mode.
-		// TODO(sonia,will): Switch serveAPI over to always require TS auth when we're ready
-		// to remove the debug flags.
-		// For now, existing client uses platform auth (else case below).
-
-		if r.URL.Path == "/api/auth" {
-			// Serve auth, which creates a new session for the user to authenticate,
-			// in the case that the request doesn't already have one.
-			s.serveTailscaleAuth(w, r)
-			return
-		}
-		// For all other endpoints, require a valid session to proceed.
-		session, err := s.getTailscaleBrowserSession(r)
-		if err != nil || !session.isAuthorized() {
-			http.Error(w, "no valid session", http.StatusUnauthorized)
-			return
-		}
-	} else if ok := authorizePlatformRequest(w, r); !ok {
-		return
-	}
-
 	w.Header().Set("X-CSRF-Token", csrf.Token(r))
 	path := strings.TrimPrefix(r.URL.Path, "/api")
 	switch {
@@ -415,6 +520,12 @@ func (s *Server) serveGetNodeData(w http.ResponseWriter, r *http.Request) {
 	profile := st.User[st.Self.UserID]
 	deviceName := strings.Split(st.Self.DNSName, ".")[0]
 	versionShort := strings.Split(st.Version, "-")[0]
+	var debugMode string
+	if s.mode == ManageServerMode {
+		debugMode = "full"
+	} else if s.mode == LoginServerMode {
+		debugMode = "login"
+	}
 	data := &nodeData{
 		Profile:     profile,
 		Status:      st.BackendState,
@@ -426,10 +537,8 @@ func (s *Server) serveGetNodeData(w http.ResponseWriter, r *http.Request) {
 		IsUnraid:    distro.Get() == distro.Unraid,
 		UnraidToken: os.Getenv("UNRAID_CSRF_TOKEN"),
 		IPNVersion:  versionShort,
-		DebugMode:   s.tsDebugMode,
+		DebugMode:   debugMode, // TODO(sonia,will): just pass back s.mode directly?
 	}
-	exitNodeRouteV4 := netip.MustParsePrefix("0.0.0.0/0")
-	exitNodeRouteV6 := netip.MustParsePrefix("::/0")
 	for _, r := range prefs.AdvertiseRoutes {
 		if r == exitNodeRouteV4 || r == exitNodeRouteV6 {
 			data.AdvertiseExitNode = true
@@ -443,11 +552,7 @@ func (s *Server) serveGetNodeData(w http.ResponseWriter, r *http.Request) {
 	if len(st.TailscaleIPs) != 0 {
 		data.IP = st.TailscaleIPs[0].String()
 	}
-	if err := json.NewEncoder(w).Encode(*data); err != nil {
-		http.Error(w, err.Error(), http.StatusInternalServerError)
-		return
-	}
-	w.Header().Set("Content-Type", "application/json")
+	writeJSON(w, *data)
 }
 
 type nodeUpdate struct {
@@ -474,6 +579,22 @@ func (s *Server) servePostNodeUpdate(w http.ResponseWriter, r *http.Request) {
 		return
 	}
 
+	prefs, err := s.lc.GetPrefs(r.Context())
+	if err != nil {
+		http.Error(w, err.Error(), http.StatusInternalServerError)
+		return
+	}
+
+	isCurrentlyExitNode := slices.Contains(prefs.AdvertiseRoutes, exitNodeRouteV4) || slices.Contains(prefs.AdvertiseRoutes, exitNodeRouteV6)
+
+	if postData.AdvertiseExitNode != isCurrentlyExitNode {
+		if postData.AdvertiseExitNode {
+			s.lc.IncrementCounter(r.Context(), "web_client_advertise_exitnode_enable", 1)
+		} else {
+			s.lc.IncrementCounter(r.Context(), "web_client_advertise_exitnode_disable", 1)
+		}
+	}
+
 	routes, err := netutil.CalcAdvertiseRoutes(postData.AdvertiseRoutes, postData.AdvertiseExitNode)
 	if err != nil {
 		w.WriteHeader(http.StatusInternalServerError)
@@ -486,7 +607,7 @@ func (s *Server) servePostNodeUpdate(w http.ResponseWriter, r *http.Request) {
 	}
 	mp.Prefs.WantRunning = true
 	mp.Prefs.AdvertiseRoutes = routes
-	log.Printf("Doing edit: %v", mp.Pretty())
+	s.logf("Doing edit: %v", mp.Pretty())
 
 	if _, err := s.lc.EditPrefs(r.Context(), mp); err != nil {
 		w.WriteHeader(http.StatusInternalServerError)
@@ -502,9 +623,9 @@ func (s *Server) servePostNodeUpdate(w http.ResponseWriter, r *http.Request) {
 	if postData.ForceLogout {
 		logout = true
 	}
-	log.Printf("tailscaleUp(reauth=%v, logout=%v) ...", reauth, logout)
+	s.logf("tailscaleUp(reauth=%v, logout=%v) ...", reauth, logout)
 	url, err := s.tailscaleUp(r.Context(), st, postData)
-	log.Printf("tailscaleUp = (URL %v, %v)", url != "", err)
+	s.logf("tailscaleUp = (URL %v, %v)", url != "", err)
 	if err != nil {
 		w.WriteHeader(http.StatusInternalServerError)
 		json.NewEncoder(w).Encode(mi{"error": err.Error()})
@@ -689,3 +810,12 @@ func enforcePrefix(prefix string, h http.HandlerFunc) http.HandlerFunc {
 		http.StripPrefix(prefix, h).ServeHTTP(w, r)
 	}
 }
+
+func writeJSON(w http.ResponseWriter, data any) {
+	w.Header().Set("Content-Type", "application/json")
+	if err := json.NewEncoder(w).Encode(data); err != nil {
+		w.Header().Set("Content-Type", "text/plain")
+		http.Error(w, err.Error(), http.StatusInternalServerError)
+		return
+	}
+}

client/web/web_test.go

@@ -10,6 +10,7 @@ import (
 	"io"
 	"net/http"
 	"net/http/httptest"
+	"net/netip"
 	"net/url"
 	"strings"
 	"testing"
@@ -22,6 +23,7 @@ import (
 	"tailscale.com/net/memnet"
 	"tailscale.com/tailcfg"
 	"tailscale.com/types/views"
+	"tailscale.com/util/httpm"
 )
 
 func TestQnapAuthnURL(t *testing.T) {
@@ -124,7 +126,7 @@ func TestServeAPI(t *testing.T) {
 			res := w.Result()
 			defer res.Body.Close()
 			if gotStatus := res.StatusCode; tt.wantStatus != gotStatus {
-				t.Errorf("wrong status; want=%q, got=%q", tt.wantStatus, gotStatus)
+				t.Errorf("wrong status; want=%v, got=%v", tt.wantStatus, gotStatus)
 			}
 			body, err := io.ReadAll(res.Body)
 			if err != nil {
@@ -150,76 +152,50 @@ func TestGetTailscaleBrowserSession(t *testing.T) {
 	tags := views.SliceOf([]string{"tag:server"})
 	tailnetNodes := map[string]*apitype.WhoIsResponse{
 		userANodeIP: {
-			Node:        &tailcfg.Node{StableID: "Node1"},
+			Node:        &tailcfg.Node{ID: 1, StableID: "1"},
 			UserProfile: userA,
 		},
 		userBNodeIP: {
-			Node:        &tailcfg.Node{StableID: "Node2"},
+			Node:        &tailcfg.Node{ID: 2, StableID: "2"},
 			UserProfile: userB,
 		},
 		taggedNodeIP: {
-			Node: &tailcfg.Node{StableID: "Node3", Tags: tags.AsSlice()},
+			Node: &tailcfg.Node{ID: 3, StableID: "3", Tags: tags.AsSlice()},
 		},
 	}
 
 	lal := memnet.Listen("local-tailscaled.sock:80")
 	defer lal.Close()
-	// Serve a testing localapi handler so we can simulate
-	// whois responses without a functioning tailnet.
-	localapi := &http.Server{Handler: http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
-		switch r.URL.Path {
-		case "/localapi/v0/whois":
-			addr := r.URL.Query().Get("addr")
-			if addr == "" {
-				t.Fatalf("/whois call missing \"addr\" query")
-			}
-			if node := tailnetNodes[addr]; node != nil {
-				if err := json.NewEncoder(w).Encode(&node); err != nil {
-					http.Error(w, err.Error(), http.StatusInternalServerError)
-					return
-				}
-				w.Header().Set("Content-Type", "application/json")
-				return
-			}
-			http.Error(w, "not a node", http.StatusUnauthorized)
-			return
-		case "/localapi/v0/status":
-			status := ipnstate.Status{Self: selfNode}
-			if err := json.NewEncoder(w).Encode(status); err != nil {
-				http.Error(w, err.Error(), http.StatusInternalServerError)
-				return
-			}
-			w.Header().Set("Content-Type", "application/json")
-			return
-		default:
-			// Only the above two endpoints get triggered from getTailscaleBrowserSession.
-			// No need to mock any of the other localapi endpoint.
-			t.Fatalf("unhandled localapi test endpoint %q, add to localapi handler func in test", r.URL.Path)
-		}
-	})}
+	localapi := mockLocalAPI(t, tailnetNodes, func() *ipnstate.PeerStatus { return selfNode })
 	defer localapi.Close()
 	go localapi.Serve(lal)
 
-	s := &Server{lc: &tailscale.LocalClient{Dial: lal.Dial}}
+	s := &Server{
+		timeNow: time.Now,
+		lc:      &tailscale.LocalClient{Dial: lal.Dial},
+	}
 
 	// Add some browser sessions to cache state.
 	userASession := &browserSession{
 		ID:            "cookie1",
-		SrcNode:       "Node1",
+		SrcNode:       1,
 		SrcUser:       userA.ID,
-		Authenticated: time.Time{}, // not yet authenticated
+		Created:       time.Now(),
+		Authenticated: false, // not yet authenticated
 	}
 	userBSession := &browserSession{
 		ID:            "cookie2",
-		SrcNode:       "Node2",
+		SrcNode:       2,
 		SrcUser:       userB.ID,
-		Authenticated: time.Now().Add(-2 * sessionCookieExpiry), // expired
+		Created:       time.Now().Add(-2 * sessionCookieExpiry),
+		Authenticated: true, // expired
 	}
 	userASessionAuthorized := &browserSession{
 		ID:            "cookie3",
-		SrcNode:       "Node1",
+		SrcNode:       1,
 		SrcUser:       userA.ID,
-		Authenticated: time.Now(), // authenticated and not expired
+		Created:       time.Now(),
+		Authenticated: true, // authenticated and not expired
 	}
 	s.browserSessions.Store(userASession.ID, userASession)
 	s.browserSessions.Store(userBSession.ID, userBSession)
@@ -265,11 +241,26 @@ func TestGetTailscaleBrowserSession(t *testing.T) {
 			wantError:   errNotOwner,
 		},
 		{
-			name:        "tagged-source",
+			name:        "tagged-remote-source",
 			selfNode:    &ipnstate.PeerStatus{ID: "self", UserID: userA.ID},
 			remoteAddr:  taggedNodeIP,
 			wantSession: nil,
-			wantError:   errTaggedSource,
+			wantError:   errTaggedRemoteSource,
+		},
+		{
+			name:        "tagged-local-source",
+			selfNode:    &ipnstate.PeerStatus{ID: "3"},
+			remoteAddr:  taggedNodeIP, // same node as selfNode
+			wantSession: nil,
+			wantError:   errTaggedLocalSource,
+		},
+		{
+			name:        "not-tagged-local-source",
+			selfNode:    &ipnstate.PeerStatus{ID: "1", UserID: userA.ID},
+			remoteAddr:  userANodeIP, // same node as selfNode
+			cookie:      userASession.ID,
+			wantSession: userASession,
+			wantError:   nil, // should not error
 		},
 		{
 			name:        "has-session",
@@ -312,16 +303,514 @@ func TestGetTailscaleBrowserSession(t *testing.T) {
 			if tt.cookie != "" {
 				r.AddCookie(&http.Cookie{Name: sessionCookieName, Value: tt.cookie})
 			}
-			session, err := s.getTailscaleBrowserSession(r)
+			session, _, err := s.getSession(r)
 			if !errors.Is(err, tt.wantError) {
 				t.Errorf("wrong error; want=%v, got=%v", tt.wantError, err)
 			}
 			if diff := cmp.Diff(session, tt.wantSession); diff != "" {
 				t.Errorf("wrong session; (-got+want):%v", diff)
 			}
-			if gotIsAuthorized := session.isAuthorized(); gotIsAuthorized != tt.wantIsAuthorized {
+			if gotIsAuthorized := session.isAuthorized(s.timeNow()); gotIsAuthorized != tt.wantIsAuthorized {
 				t.Errorf("wrong isAuthorized; want=%v, got=%v", tt.wantIsAuthorized, gotIsAuthorized)
 			}
 		})
 	}
 }
+
+// TestAuthorizeRequest tests the s.authorizeRequest function.
+// 2023-10-18: These tests currently cover tailscale auth mode (not platform auth).
+func TestAuthorizeRequest(t *testing.T) {
+	// Create self and remoteNode owned by same user.
+	// See TestGetTailscaleBrowserSession for tests of
+	// browser sessions w/ different users.
+	user := &tailcfg.UserProfile{ID: tailcfg.UserID(1)}
+	self := &ipnstate.PeerStatus{ID: "self", UserID: user.ID}
+	remoteNode := &apitype.WhoIsResponse{Node: &tailcfg.Node{StableID: "node"}, UserProfile: user}
+	remoteIP := "100.100.100.101"
+
+	lal := memnet.Listen("local-tailscaled.sock:80")
+	defer lal.Close()
+	localapi := mockLocalAPI(t,
+		map[string]*apitype.WhoIsResponse{remoteIP: remoteNode},
+		func() *ipnstate.PeerStatus { return self },
+	)
+	defer localapi.Close()
+	go localapi.Serve(lal)
+
+	s := &Server{
+		mode:    ManageServerMode,
+		lc:      &tailscale.LocalClient{Dial: lal.Dial},
+		timeNow: time.Now,
+	}
+	validCookie := "ts-cookie"
+	s.browserSessions.Store(validCookie, &browserSession{
+		ID:            validCookie,
+		SrcNode:       remoteNode.Node.ID,
+		SrcUser:       user.ID,
+		Created:       time.Now(),
+		Authenticated: true,
+	})
+
+	tests := []struct {
+		reqPath   string
+		reqMethod string
+
+		wantOkNotOverTailscale bool // simulates req over public internet
+		wantOkWithoutSession   bool // simulates req over TS without valid browser session
+		wantOkWithSession      bool // simulates req over TS with valid browser session
+	}{{
+		reqPath:                "/api/data",
+		reqMethod:              httpm.GET,
+		wantOkNotOverTailscale: false,
+		wantOkWithoutSession:   true,
+		wantOkWithSession:      true,
+	}, {
+		reqPath:                "/api/data",
+		reqMethod:              httpm.POST,
+		wantOkNotOverTailscale: false,
+		wantOkWithoutSession:   false,
+		wantOkWithSession:      true,
+	}, {
+		reqPath:                "/api/somethingelse",
+		reqMethod:              httpm.GET,
+		wantOkNotOverTailscale: false,
+		wantOkWithoutSession:   false,
+		wantOkWithSession:      true,
+	}, {
+		reqPath:                "/assets/styles.css",
+		wantOkNotOverTailscale: false,
+		wantOkWithoutSession:   true,
+		wantOkWithSession:      true,
+	}}
+	for _, tt := range tests {
+		t.Run(fmt.Sprintf("%s-%s", tt.reqMethod, tt.reqPath), func(t *testing.T) {
+			doAuthorize := func(remoteAddr string, cookie string) bool {
+				r := httptest.NewRequest(tt.reqMethod, tt.reqPath, nil)
+				r.RemoteAddr = remoteAddr
+				if cookie != "" {
+					r.AddCookie(&http.Cookie{Name: sessionCookieName, Value: cookie})
+				}
+				w := httptest.NewRecorder()
+				return s.authorizeRequest(w, r)
+			}
+			// Do request from non-Tailscale IP.
+			if gotOk := doAuthorize("123.456.789.999", ""); gotOk != tt.wantOkNotOverTailscale {
+				t.Errorf("wantOkNotOverTailscale; want=%v, got=%v", tt.wantOkNotOverTailscale, gotOk)
+			}
+			// Do request from Tailscale IP w/o associated session.
+			if gotOk := doAuthorize(remoteIP, ""); gotOk != tt.wantOkWithoutSession {
+				t.Errorf("wantOkWithoutSession; want=%v, got=%v", tt.wantOkWithoutSession, gotOk)
+			}
+			// Do request from Tailscale IP w/ associated session.
+			if gotOk := doAuthorize(remoteIP, validCookie); gotOk != tt.wantOkWithSession {
+				t.Errorf("wantOkWithSession; want=%v, got=%v", tt.wantOkWithSession, gotOk)
+			}
+		})
+	}
+}
+
+func TestServeAuth(t *testing.T) {
+	user := &tailcfg.UserProfile{ID: tailcfg.UserID(1)}
+	self := &ipnstate.PeerStatus{
+		ID:           "self",
+		UserID:       user.ID,
+		TailscaleIPs: []netip.Addr{netip.MustParseAddr("100.1.2.3")},
+	}
+	remoteNode := &apitype.WhoIsResponse{Node: &tailcfg.Node{ID: 1}, UserProfile: user}
+	remoteIP := "100.100.100.101"
+
+	lal := memnet.Listen("local-tailscaled.sock:80")
+	defer lal.Close()
+	localapi := mockLocalAPI(t,
+		map[string]*apitype.WhoIsResponse{remoteIP: remoteNode},
+		func() *ipnstate.PeerStatus { return self },
+	)
+	defer localapi.Close()
+	go localapi.Serve(lal)
+
+	timeNow := time.Now()
+	oneHourAgo := timeNow.Add(-time.Hour)
+	sixtyDaysAgo := timeNow.Add(-sessionCookieExpiry * 2)
+
+	s := &Server{
+		mode:    ManageServerMode,
+		lc:      &tailscale.LocalClient{Dial: lal.Dial},
+		timeNow: func() time.Time { return timeNow },
+	}
+
+	successCookie := "ts-cookie-success"
+	s.browserSessions.Store(successCookie, &browserSession{
+		ID:      successCookie,
+		SrcNode: remoteNode.Node.ID,
+		SrcUser: user.ID,
+		Created: oneHourAgo,
+		AuthID:  testAuthPathSuccess,
+		AuthURL: testControlURL + testAuthPathSuccess,
+	})
+	failureCookie := "ts-cookie-failure"
+	s.browserSessions.Store(failureCookie, &browserSession{
+		ID:      failureCookie,
+		SrcNode: remoteNode.Node.ID,
+		SrcUser: user.ID,
+		Created: oneHourAgo,
+		AuthID:  testAuthPathError,
+		AuthURL: testControlURL + testAuthPathError,
+	})
+	expiredCookie := "ts-cookie-expired"
+	s.browserSessions.Store(expiredCookie, &browserSession{
+		ID:      expiredCookie,
+		SrcNode: remoteNode.Node.ID,
+		SrcUser: user.ID,
+		Created: sixtyDaysAgo,
+		AuthID:  "/a/old-auth-url",
+		AuthURL: testControlURL + "/a/old-auth-url",
+	})
+
+	tests := []struct {
+		name string
+
+		cookie        string          // cookie attached to request
+		wantNewCookie bool            // want new cookie generated during request
+		wantSession   *browserSession // session associated w/ cookie after request
+
+		path       string
+		wantStatus int
+		wantResp   any
+	}{
+		{
+			name:          "no-session",
+			path:          "/api/auth",
+			wantStatus:    http.StatusOK,
+			wantResp:      &authResponse{OK: false, AuthNeeded: tailscaleAuth},
+			wantNewCookie: false,
+			wantSession:   nil,
+		},
+		{
+			name:          "new-session",
+			path:          "/api/auth/session/new",
+			wantStatus:    http.StatusOK,
+			wantResp:      &newSessionAuthResponse{AuthURL: testControlURL + testAuthPath},
+			wantNewCookie: true,
+			wantSession: &browserSession{
+				ID:            "GENERATED_ID", // gets swapped for newly created ID by test
+				SrcNode:       remoteNode.Node.ID,
+				SrcUser:       user.ID,
+				Created:       timeNow,
+				AuthID:        testAuthPath,
+				AuthURL:       testControlURL + testAuthPath,
+				Authenticated: false,
+			},
+		},
+		{
+			name:       "query-existing-incomplete-session",
+			path:       "/api/auth",
+			cookie:     successCookie,
+			wantStatus: http.StatusOK,
+			wantResp:   &authResponse{OK: false, AuthNeeded: tailscaleAuth},
+			wantSession: &browserSession{
+				ID:            successCookie,
+				SrcNode:       remoteNode.Node.ID,
+				SrcUser:       user.ID,
+				Created:       oneHourAgo,
+				AuthID:        testAuthPathSuccess,
+				AuthURL:       testControlURL + testAuthPathSuccess,
+				Authenticated: false,
+			},
+		},
+		{
+			name:       "existing-session-used",
+			path:       "/api/auth/session/new", // should not create new session
+			cookie:     successCookie,
+			wantStatus: http.StatusOK,
+			wantResp:   &newSessionAuthResponse{AuthURL: testControlURL + testAuthPathSuccess},
+			wantSession: &browserSession{
+				ID:            successCookie,
+				SrcNode:       remoteNode.Node.ID,
+				SrcUser:       user.ID,
+				Created:       oneHourAgo,
+				AuthID:        testAuthPathSuccess,
+				AuthURL:       testControlURL + testAuthPathSuccess,
+				Authenticated: false,
+			},
+		},
+		{
+			name:       "transition-to-successful-session",
+			path:       "/api/auth/session/wait",
+			cookie:     successCookie,
+			wantStatus: http.StatusOK,
+			wantResp:   nil,
+			wantSession: &browserSession{
+				ID:            successCookie,
+				SrcNode:       remoteNode.Node.ID,
+				SrcUser:       user.ID,
+				Created:       oneHourAgo,
+				AuthID:        testAuthPathSuccess,
+				AuthURL:       testControlURL + testAuthPathSuccess,
+				Authenticated: true,
+			},
+		},
+		{
+			name:       "query-existing-complete-session",
+			path:       "/api/auth",
+			cookie:     successCookie,
+			wantStatus: http.StatusOK,
+			wantResp:   &authResponse{OK: true},
+			wantSession: &browserSession{
+				ID:            successCookie,
+				SrcNode:       remoteNode.Node.ID,
+				SrcUser:       user.ID,
+				Created:       oneHourAgo,
+				AuthID:        testAuthPathSuccess,
+				AuthURL:       testControlURL + testAuthPathSuccess,
+				Authenticated: true,
+			},
+		},
+		{
+			name:        "transition-to-failed-session",
+			path:        "/api/auth/session/wait",
+			cookie:      failureCookie,
+			wantStatus:  http.StatusUnauthorized,
+			wantResp:    nil,
+			wantSession: nil, // session deleted
+		},
+		{
+			name:          "failed-session-cleaned-up",
+			path:          "/api/auth/session/new",
+			cookie:        failureCookie,
+			wantStatus:    http.StatusOK,
+			wantResp:      &newSessionAuthResponse{AuthURL: testControlURL + testAuthPath},
+			wantNewCookie: true,
+			wantSession: &browserSession{
+				ID:            "GENERATED_ID",
+				SrcNode:       remoteNode.Node.ID,
+				SrcUser:       user.ID,
+				Created:       timeNow,
+				AuthID:        testAuthPath,
+				AuthURL:       testControlURL + testAuthPath,
+				Authenticated: false,
+			},
+		},
+		{
+			name:          "expired-cookie-gets-new-session",
+			path:          "/api/auth/session/new",
+			cookie:        expiredCookie,
+			wantStatus:    http.StatusOK,
+			wantResp:      &newSessionAuthResponse{AuthURL: testControlURL + testAuthPath},
+			wantNewCookie: true,
+			wantSession: &browserSession{
+				ID:            "GENERATED_ID",
+				SrcNode:       remoteNode.Node.ID,
+				SrcUser:       user.ID,
+				Created:       timeNow,
+				AuthID:        testAuthPath,
+				AuthURL:       testControlURL + testAuthPath,
+				Authenticated: false,
+			},
+		},
+	}
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			r := httptest.NewRequest("GET", "http://100.1.2.3:5252"+tt.path, nil)
+			r.RemoteAddr = remoteIP
+			r.AddCookie(&http.Cookie{Name: sessionCookieName, Value: tt.cookie})
+			w := httptest.NewRecorder()
+			s.serve(w, r)
+			res := w.Result()
+			defer res.Body.Close()
+
+			// Validate response status/data.
+			if gotStatus := res.StatusCode; tt.wantStatus != gotStatus {
+				t.Errorf("wrong status; want=%v, got=%v", tt.wantStatus, gotStatus)
+			}
+			var gotResp string
+			if res.StatusCode == http.StatusOK {
+				body, err := io.ReadAll(res.Body)
+				if err != nil {
+					t.Fatal(err)
+				}
+				gotResp = strings.Trim(string(body), "\n")
+			}
+			var wantResp string
+			if tt.wantResp != nil {
+				b, _ := json.Marshal(tt.wantResp)
+				wantResp = string(b)
+			}
+			if diff := cmp.Diff(gotResp, string(wantResp)); diff != "" {
+				t.Errorf("wrong response; (-got+want):%v", diff)
+			}
+			// Validate cookie creation.
+			sessionID := tt.cookie
+			var gotCookie bool
+			for _, c := range w.Result().Cookies() {
+				if c.Name == sessionCookieName {
+					gotCookie = true
+					sessionID = c.Value
+					break
+				}
+			}
+			if gotCookie != tt.wantNewCookie {
+				t.Errorf("wantNewCookie wrong; want=%v, got=%v", tt.wantNewCookie, gotCookie)
+			}
+			// Validate browser session contents.
+			var gotSesson *browserSession
+			if s, ok := s.browserSessions.Load(sessionID); ok {
+				gotSesson = s.(*browserSession)
+			}
+			if tt.wantSession != nil && tt.wantSession.ID == "GENERATED_ID" {
+				// If requested, swap in the generated session ID before
+				// comparing got/want.
+				tt.wantSession.ID = sessionID
+			}
+			if diff := cmp.Diff(gotSesson, tt.wantSession); diff != "" {
+				t.Errorf("wrong session; (-got+want):%v", diff)
+			}
+		})
+	}
+}
+
+func TestRequireTailscaleIP(t *testing.T) {
+	self := &ipnstate.PeerStatus{
+		TailscaleIPs: []netip.Addr{
+			netip.MustParseAddr("100.1.2.3"),
+			netip.MustParseAddr("fd7a:115c::1234"),
+		},
+	}
+
+	lal := memnet.Listen("local-tailscaled.sock:80")
+	defer lal.Close()
+	localapi := mockLocalAPI(t, nil, func() *ipnstate.PeerStatus { return self })
+	defer localapi.Close()
+	go localapi.Serve(lal)
+
+	s := &Server{
+		mode:    ManageServerMode,
+		lc:      &tailscale.LocalClient{Dial: lal.Dial},
+		timeNow: time.Now,
+		logf:    t.Logf,
+	}
+
+	tests := []struct {
+		name         string
+		target       string
+		wantHandled  bool
+		wantLocation string
+	}{
+		{
+			name:         "localhost",
+			target:       "http://localhost/",
+			wantHandled:  true,
+			wantLocation: "http://100.1.2.3:5252/",
+		},
+		{
+			name:         "ipv4-no-port",
+			target:       "http://100.1.2.3/",
+			wantHandled:  true,
+			wantLocation: "http://100.1.2.3:5252/",
+		},
+		{
+			name:        "ipv4-correct-port",
+			target:      "http://100.1.2.3:5252/",
+			wantHandled: false,
+		},
+		{
+			name:         "ipv6-no-port",
+			target:       "http://[fd7a:115c::1234]/",
+			wantHandled:  true,
+			wantLocation: "http://100.1.2.3:5252/",
+		},
+		{
+			name:        "ipv6-correct-port",
+			target:      "http://[fd7a:115c::1234]:5252/",
+			wantHandled: false,
+		},
+		{
+			name:        "quad-100",
+			target:      "http://100.100.100.100/",
+			wantHandled: false,
+		},
+		{
+			name:        "ipv6-service-addr",
+			target:      "http://[fd7a:115c:a1e0::53]/",
+			wantHandled: false,
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.target, func(t *testing.T) {
+			s.logf = t.Logf
+			r := httptest.NewRequest(httpm.GET, tt.target, nil)
+			w := httptest.NewRecorder()
+			handled := s.requireTailscaleIP(w, r)
+
+			if handled != tt.wantHandled {
+				t.Errorf("request(%q) was handled; want=%v, got=%v", tt.target, tt.wantHandled, handled)
+			}
+
+			location := w.Header().Get("Location")
+			if location != tt.wantLocation {
+				t.Errorf("request(%q) wrong location; want=%q, got=%q", tt.target, tt.wantLocation, location)
+			}
+		})
+	}
+}
+
+var (
+	testControlURL      = "http://localhost:8080"
+	testAuthPath        = "/a/12345"
+	testAuthPathSuccess = "/a/will-succeed"
+	testAuthPathError   = "/a/will-error"
+)
+
+// mockLocalAPI constructs a test localapi handler that can be used
+// to simulate localapi responses without a functioning tailnet.
+//
+// self accepts a function that resolves to a self node status,
+// so that tests may swap out the /localapi/v0/status response
+// as desired.
+func mockLocalAPI(t *testing.T, whoIs map[string]*apitype.WhoIsResponse, self func() *ipnstate.PeerStatus) *http.Server {
+	return &http.Server{Handler: http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		switch r.URL.Path {
+		case "/localapi/v0/whois":
+			addr := r.URL.Query().Get("addr")
+			if addr == "" {
+				t.Fatalf("/whois call missing \"addr\" query")
+			}
+			if node := whoIs[addr]; node != nil {
+				writeJSON(w, &node)
+				return
+			}
+			http.Error(w, "not a node", http.StatusUnauthorized)
+			return
+		case "/localapi/v0/status":
+			writeJSON(w, ipnstate.Status{Self: self()})
+			return
+		case "/localapi/v0/debug-web-client": // used by TestServeTailscaleAuth
+			type reqData struct {
+				ID  string
+				Src tailcfg.NodeID
+			}
+			var data reqData
+			if err := json.NewDecoder(r.Body).Decode(&data); err != nil {
+				http.Error(w, "invalid JSON body", http.StatusBadRequest)
+				return
+			}
+			if data.Src == 0 {
+				http.Error(w, "missing Src node", http.StatusBadRequest)
+				return
+			}
+			var resp *tailcfg.WebClientAuthResponse
+			if data.ID == "" {
+				resp = &tailcfg.WebClientAuthResponse{ID: testAuthPath, URL: testControlURL + testAuthPath}
+			} else if data.ID == testAuthPathSuccess {
+				resp = &tailcfg.WebClientAuthResponse{Complete: true}
+			} else if data.ID == testAuthPathError {
+				http.Error(w, "authenticated as wrong user", http.StatusUnauthorized)
+				return
+			}
+			writeJSON(w, resp)
+			return
+		default:
+			t.Fatalf("unhandled localapi test endpoint %q, add to localapi handler func in test", r.URL.Path)
+		}
+	})}
+}

client/web/yarn.lock

@@ -23,6 +23,14 @@
     "@babel/highlight" "^7.22.10"
     chalk "^2.4.2"
 
+"@babel/code-frame@^7.22.13":
+  version "7.22.13"
+  resolved "https://registry.yarnpkg.com/@babel/code-frame/-/code-frame-7.22.13.tgz#e3c1c099402598483b7a8c46a721d1038803755e"
+  integrity sha512-XktuhWlJ5g+3TJXc5upd9Ks1HutSArik6jf2eAjYFyIOf4ej3RN+184cZbzDvbPnuTJIUhPKKJE3cIsYTiAT3w==
+  dependencies:
+    "@babel/highlight" "^7.22.13"
+    chalk "^2.4.2"
+
 "@babel/compat-data@^7.22.9":
   version "7.22.9"
   resolved "https://registry.yarnpkg.com/@babel/compat-data/-/compat-data-7.22.9.tgz#71cdb00a1ce3a329ce4cbec3a44f9fef35669730"
@@ -59,6 +67,16 @@
     "@jridgewell/trace-mapping" "^0.3.17"
     jsesc "^2.5.1"
 
+"@babel/generator@^7.23.0":
+  version "7.23.0"
+  resolved "https://registry.yarnpkg.com/@babel/generator/-/generator-7.23.0.tgz#df5c386e2218be505b34837acbcb874d7a983420"
+  integrity sha512-lN85QRR+5IbYrMWM6Y4pE/noaQtg4pNiqeNGX60eqOfo6gtEj6uw/JagelB8vVztSd7R6M5n1+PQkDbHbBRU4g==
+  dependencies:
+    "@babel/types" "^7.23.0"
+    "@jridgewell/gen-mapping" "^0.3.2"
+    "@jridgewell/trace-mapping" "^0.3.17"
+    jsesc "^2.5.1"
+
 "@babel/helper-compilation-targets@^7.22.10":
   version "7.22.10"
   resolved "https://registry.yarnpkg.com/@babel/helper-compilation-targets/-/helper-compilation-targets-7.22.10.tgz#01d648bbc25dd88f513d862ee0df27b7d4e67024"
@@ -70,18 +88,23 @@
     lru-cache "^5.1.1"
     semver "^6.3.1"
 
+"@babel/helper-environment-visitor@^7.22.20":
+  version "7.22.20"
+  resolved "https://registry.yarnpkg.com/@babel/helper-environment-visitor/-/helper-environment-visitor-7.22.20.tgz#96159db61d34a29dba454c959f5ae4a649ba9167"
+  integrity sha512-zfedSIzFhat/gFhWfHtgWvlec0nqB9YEIVrpuwjruLlXfUSnA8cJB0miHKwqDnQ7d32aKo2xt88/xZptwxbfhA==
+
 "@babel/helper-environment-visitor@^7.22.5":
   version "7.22.5"
   resolved "https://registry.yarnpkg.com/@babel/helper-environment-visitor/-/helper-environment-visitor-7.22.5.tgz#f06dd41b7c1f44e1f8da6c4055b41ab3a09a7e98"
   integrity sha512-XGmhECfVA/5sAt+H+xpSg0mfrHq6FzNr9Oxh7PSEBBRUb/mL7Kz3NICXb194rCqAEdxkhPT1a88teizAFyvk8Q==
 
-"@babel/helper-function-name@^7.22.5":
-  version "7.22.5"
-  resolved "https://registry.yarnpkg.com/@babel/helper-function-name/-/helper-function-name-7.22.5.tgz#ede300828905bb15e582c037162f99d5183af1be"
-  integrity sha512-wtHSq6jMRE3uF2otvfuD3DIvVhOsSNshQl0Qrd7qC9oQJzHvOL4qQXlQn2916+CXGywIjpGuIkoyZRRxHPiNQQ==
+"@babel/helper-function-name@^7.23.0":
+  version "7.23.0"
+  resolved "https://registry.yarnpkg.com/@babel/helper-function-name/-/helper-function-name-7.23.0.tgz#1f9a3cdbd5b2698a670c30d2735f9af95ed52759"
+  integrity sha512-OErEqsrxjZTJciZ4Oo+eoZqeW9UIiOcuYKRJA4ZAgV9myA+pOXhhmpfNCKjEH/auVfEYVFJ6y1Tc4r0eIApqiw==
   dependencies:
-    "@babel/template" "^7.22.5"
-    "@babel/types" "^7.22.5"
+    "@babel/template" "^7.22.15"
+    "@babel/types" "^7.23.0"
 
 "@babel/helper-hoist-variables@^7.22.5":
   version "7.22.5"
@@ -127,6 +150,11 @@
   resolved "https://registry.yarnpkg.com/@babel/helper-string-parser/-/helper-string-parser-7.22.5.tgz#533f36457a25814cf1df6488523ad547d784a99f"
   integrity sha512-mM4COjgZox8U+JcXQwPijIZLElkgEpO5rsERVDJTc2qfCDfERyob6k5WegS14SX18IIjv+XD+GrqNumY5JRCDw==
 
+"@babel/helper-validator-identifier@^7.22.20":
+  version "7.22.20"
+  resolved "https://registry.yarnpkg.com/@babel/helper-validator-identifier/-/helper-validator-identifier-7.22.20.tgz#c4ae002c61d2879e724581d96665583dbc1dc0e0"
+  integrity sha512-Y4OZ+ytlatR8AI+8KZfKuL5urKp7qey08ha31L8b3BwewJAoJamTzyvxPR/5D+KkdJCGPq/+8TukHBlY10FX9A==
+
 "@babel/helper-validator-identifier@^7.22.5":
   version "7.22.5"
   resolved "https://registry.yarnpkg.com/@babel/helper-validator-identifier/-/helper-validator-identifier-7.22.5.tgz#9544ef6a33999343c8740fa51350f30eeaaaf193"
@@ -155,11 +183,34 @@
     chalk "^2.4.2"
     js-tokens "^4.0.0"
 
+"@babel/highlight@^7.22.13":
+  version "7.22.20"
+  resolved "https://registry.yarnpkg.com/@babel/highlight/-/highlight-7.22.20.tgz#4ca92b71d80554b01427815e06f2df965b9c1f54"
+  integrity sha512-dkdMCN3py0+ksCgYmGG8jKeGA/8Tk+gJwSYYlFGxG5lmhfKNoAy004YpLxpS1W2J8m/EK2Ew+yOs9pVRwO89mg==
+  dependencies:
+    "@babel/helper-validator-identifier" "^7.22.20"
+    chalk "^2.4.2"
+    js-tokens "^4.0.0"
+
 "@babel/parser@^7.22.10", "@babel/parser@^7.22.5":
   version "7.22.10"
   resolved "https://registry.yarnpkg.com/@babel/parser/-/parser-7.22.10.tgz#e37634f9a12a1716136c44624ef54283cabd3f55"
   integrity sha512-lNbdGsQb9ekfsnjFGhEiF4hfFqGgfOP3H3d27re3n+CGhNuTSUEQdfWk556sTLNTloczcdM5TYF2LhzmDQKyvQ==
 
+"@babel/parser@^7.22.15", "@babel/parser@^7.23.0":
+  version "7.23.0"
+  resolved "https://registry.yarnpkg.com/@babel/parser/-/parser-7.23.0.tgz#da950e622420bf96ca0d0f2909cdddac3acd8719"
+  integrity sha512-vvPKKdMemU85V9WE/l5wZEmImpCtLqbnTvqDS2U1fJ96KrxoW7KrXhNsNCblQlg8Ck4b85yxdTyelsMUgFUXiw==
+
+"@babel/template@^7.22.15":
+  version "7.22.15"
+  resolved "https://registry.yarnpkg.com/@babel/template/-/template-7.22.15.tgz#09576efc3830f0430f4548ef971dde1350ef2f38"
+  integrity sha512-QPErUVm4uyJa60rkI73qneDacvdvzxshT3kksGqlGWYdOTIUOwJ7RDUL8sGqslY1uXWSL6xMFKEXDS3ox2uF0w==
+  dependencies:
+    "@babel/code-frame" "^7.22.13"
+    "@babel/parser" "^7.22.15"
+    "@babel/types" "^7.22.15"
+
 "@babel/template@^7.22.5":
   version "7.22.5"
   resolved "https://registry.yarnpkg.com/@babel/template/-/template-7.22.5.tgz#0c8c4d944509875849bd0344ff0050756eefc6ec"
@@ -170,18 +221,18 @@
     "@babel/types" "^7.22.5"
 
 "@babel/traverse@^7.22.10":
-  version "7.22.10"
-  resolved "https://registry.yarnpkg.com/@babel/traverse/-/traverse-7.22.10.tgz#20252acb240e746d27c2e82b4484f199cf8141aa"
-  integrity sha512-Q/urqV4pRByiNNpb/f5OSv28ZlGJiFiiTh+GAHktbIrkPhPbl90+uW6SmpoLyZqutrg9AEaEf3Q/ZBRHBXgxig==
+  version "7.23.2"
+  resolved "https://registry.yarnpkg.com/@babel/traverse/-/traverse-7.23.2.tgz#329c7a06735e144a506bdb2cad0268b7f46f4ad8"
+  integrity sha512-azpe59SQ48qG6nu2CzcMLbxUudtN+dOM9kDbUqGq3HXUJRlo7i8fvPoxQUzYgLZ4cMVmuZgm8vvBpNeRhd6XSw==
   dependencies:
-    "@babel/code-frame" "^7.22.10"
-    "@babel/generator" "^7.22.10"
-    "@babel/helper-environment-visitor" "^7.22.5"
-    "@babel/helper-function-name" "^7.22.5"
+    "@babel/code-frame" "^7.22.13"
+    "@babel/generator" "^7.23.0"
+    "@babel/helper-environment-visitor" "^7.22.20"
+    "@babel/helper-function-name" "^7.23.0"
     "@babel/helper-hoist-variables" "^7.22.5"
     "@babel/helper-split-export-declaration" "^7.22.6"
-    "@babel/parser" "^7.22.10"
-    "@babel/types" "^7.22.10"
+    "@babel/parser" "^7.23.0"
+    "@babel/types" "^7.23.0"
     debug "^4.1.0"
     globals "^11.1.0"
 
@@ -194,6 +245,15 @@
     "@babel/helper-validator-identifier" "^7.22.5"
     to-fast-properties "^2.0.0"
 
+"@babel/types@^7.22.15", "@babel/types@^7.23.0":
+  version "7.23.0"
+  resolved "https://registry.yarnpkg.com/@babel/types/-/types-7.23.0.tgz#8c1f020c9df0e737e4e247c0619f58c68458aaeb"
+  integrity sha512-0oIyUfKoI3mSqMvsxBdclDwxXKXAUA8v/apZbc+iSyARYou1o8ZGDxbUYyLFoW2arqS2jDGqJuZvv1d/io1axg==
+  dependencies:
+    "@babel/helper-string-parser" "^7.22.5"
+    "@babel/helper-validator-identifier" "^7.22.20"
+    to-fast-properties "^2.0.0"
+
 "@cush/relative@^1.0.0":
   version "1.0.0"
   resolved "https://registry.yarnpkg.com/@cush/relative/-/relative-1.0.0.tgz#8cd1769bf9bde3bb27dac356b1bc94af40f6cc16"
@@ -1002,9 +1062,9 @@ gensync@^1.0.0-beta.2:
   integrity sha512-3hN7NaskYvMDLQY55gnW3NQ+mesEAepTqlg+VEbj7zzqEMBVNhzcGYYeqFo/TlYz6eQiFcp1HcsCZO+nGgS8zg==
 
 get-func-name@^2.0.0:
-  version "2.0.0"
-  resolved "https://registry.yarnpkg.com/get-func-name/-/get-func-name-2.0.0.tgz#ead774abee72e20409433a066366023dd6887a41"
-  integrity sha512-Hm0ixYtaSZ/V7C8FJrtZIuBBI+iSgL+1Aq82zSu8VQNB4S3Gk8e7Qs3VwBDJAhmRZcFqkl3tQu36g/Foh5I5ig==
+  version "2.0.2"
+  resolved "https://registry.yarnpkg.com/get-func-name/-/get-func-name-2.0.2.tgz#0d7cf20cd13fda808669ffa88f4ffc7a3943fc41"
+  integrity sha512-8vXOvuE167CtIc3OyItco7N/dpRtBbYOsPsXCz7X/PMnlGjYjSGuZJgM1Y7mmew7BKf9BqvLX2tnOVy1BBUsxQ==
 
 glob-parent@^5.1.2, glob-parent@~5.1.2:
   version "5.1.2"
@@ -1404,10 +1464,10 @@ postcss-value-parser@^4.0.0, postcss-value-parser@^4.2.0:
   resolved "https://registry.yarnpkg.com/postcss-value-parser/-/postcss-value-parser-4.2.0.tgz#723c09920836ba6d3e5af019f92bc0971c02e514"
   integrity sha512-1NNCs6uurfkVbeXG4S8JFT9t19m45ICnif8zWLd5oPSZ50QnwMfK+H3jv408d4jw/7Bttv5axS5IiHoLaVNHeQ==
 
-postcss@^8.4.23, postcss@^8.4.27:
-  version "8.4.27"
-  resolved "https://registry.yarnpkg.com/postcss/-/postcss-8.4.27.tgz#234d7e4b72e34ba5a92c29636734349e0d9c3057"
-  integrity sha512-gY/ACJtJPSmUFPDCHtX78+01fHa64FaU4zaaWfuh1MhGJISufJAH4cun6k/8fwsHYeK4UQmENQK+tRLCFJE8JQ==
+postcss@^8.4.23, postcss@^8.4.27, postcss@^8.4.31:
+  version "8.4.31"
+  resolved "https://registry.yarnpkg.com/postcss/-/postcss-8.4.31.tgz#92b451050a9f914da6755af352bdc0192508656d"
+  integrity sha512-PS08Iboia9mts/2ygV3eLpY5ghnUcfLV/EXTOW1E2qYxJKGGBUtNjN76FYHnMs36RmARn41bC0AZmn+rR0OVpQ==
   dependencies:
     nanoid "^3.3.6"
     picocolors "^1.0.0"

clientupdate/clientupdate.go

@@ -30,6 +30,7 @@ import (
 	"github.com/google/uuid"
 	"tailscale.com/clientupdate/distsign"
 	"tailscale.com/types/logger"
+	"tailscale.com/util/cmpver"
 	"tailscale.com/util/winutil"
 	"tailscale.com/version"
 	"tailscale.com/version/distro"
@@ -72,11 +73,12 @@ type Arguments struct {
 	//
 	// Leaving this empty is the same as using CurrentTrack.
 	Version string
-	// AppStore forces a local app store check, even if the current binary was
-	// not installed via an app store. TODO(cpalmer): Remove this.
-	AppStore bool
 	// Logf is a logger for update progress messages.
 	Logf logger.Logf
+	// Stdout and Stderr should be used for output instead of os.Stdout and
+	// os.Stderr.
+	Stdout io.Writer
+	Stderr io.Writer
 	// Confirm is called when a new version is available and should return true
 	// if this new version should be installed. When Confirm returns false, the
 	// update is aborted.
@@ -84,6 +86,10 @@ type Arguments struct {
 	// PkgsAddr is the address of the pkgs server to fetch updates from.
 	// Defaults to "https://pkgs.tailscale.com".
 	PkgsAddr string
+	// ForAutoUpdate should be true when Updater is created in auto-update
+	// context. When true, NewUpdater returns an error if it cannot be used for
+	// auto-updates (even if Updater.Update field is non-nil).
+	ForAutoUpdate bool
 }
 
 func (args Arguments) validate() error {
@@ -108,10 +114,20 @@ func NewUpdater(args Arguments) (*Updater, error) {
 	up := Updater{
 		Arguments: args,
 	}
-	up.Update = up.getUpdateFunction()
+	if up.Stdout == nil {
+		up.Stdout = os.Stdout
+	}
+	if up.Stderr == nil {
+		up.Stderr = os.Stderr
+	}
+	var canAutoUpdate bool
+	up.Update, canAutoUpdate = up.getUpdateFunction()
 	if up.Update == nil {
 		return nil, errors.ErrUnsupported
 	}
+	if args.ForAutoUpdate && !canAutoUpdate {
+		return nil, errors.ErrUnsupported
+	}
 	switch up.Version {
 	case StableTrack, UnstableTrack:
 		up.track = up.Version
@@ -136,52 +152,75 @@ func NewUpdater(args Arguments) (*Updater, error) {
 
 type updateFunction func() error
 
-func (up *Updater) getUpdateFunction() updateFunction {
+func (up *Updater) getUpdateFunction() (fn updateFunction, canAutoUpdate bool) {
 	switch runtime.GOOS {
 	case "windows":
-		return up.updateWindows
+		return up.updateWindows, true
 	case "linux":
 		switch distro.Get() {
 		case distro.Synology:
-			return up.updateSynology
+			// Synology updates use our own pkgs.tailscale.com instead of the
+			// Synology Package Center. We should eventually get to a regular
+			// release cadence with Synology Package Center and use their
+			// auto-update mechanism.
+			return up.updateSynology, false
 		case distro.Debian: // includes Ubuntu
-			return up.updateDebLike
+			return up.updateDebLike, true
 		case distro.Arch:
-			return up.updateArchLike
+			if up.archPackageInstalled() {
+				// Arch update func just prints a message about how to update,
+				// it doesn't support auto-updates.
+				return up.updateArchLike, false
+			}
+			return up.updateLinuxBinary, true
 		case distro.Alpine:
-			return up.updateAlpineLike
+			return up.updateAlpineLike, true
+		case distro.Unraid:
+			// Unraid runs from memory, updates must be installed via the Unraid
+			// plugin manager to be persistent.
+			// TODO(awly): implement Unraid updates using the 'plugin' CLI.
+			return nil, false
 		}
 		switch {
 		case haveExecutable("pacman"):
-			return up.updateArchLike
+			if up.archPackageInstalled() {
+				// Arch update func just prints a message about how to update,
+				// it doesn't support auto-updates.
+				return up.updateArchLike, false
+			}
+			return up.updateLinuxBinary, true
 		case haveExecutable("apt-get"): // TODO(awly): add support for "apt"
 			// The distro.Debian switch case above should catch most apt-based
 			// systems, but add this fallback just in case.
-			return up.updateDebLike
+			return up.updateDebLike, true
 		case haveExecutable("dnf"):
-			return up.updateFedoraLike("dnf")
+			return up.updateFedoraLike("dnf"), true
 		case haveExecutable("yum"):
-			return up.updateFedoraLike("yum")
+			return up.updateFedoraLike("yum"), true
 		case haveExecutable("apk"):
-			return up.updateAlpineLike
+			return up.updateAlpineLike, true
 		}
 		// If nothing matched, fall back to tarball updates.
 		if up.Update == nil {
-			return up.updateLinuxBinary
+			return up.updateLinuxBinary, true
 		}
 	case "darwin":
 		switch {
-		case !up.Arguments.AppStore && !version.IsSandboxedMacOS():
-			return nil
-		case !up.Arguments.AppStore && strings.HasSuffix(os.Getenv("HOME"), "/io.tailscale.ipn.macsys/Data"):
-			return up.updateMacSys
+		case version.IsMacAppStore():
+			// App store update func just opens the store page, it doesn't
+			// support auto-updates.
+			return up.updateMacAppStore, false
+		case version.IsMacSysExt():
+			// Macsys update func kicks off Sparkle. Auto-updates are done by
+			// Sparkle.
+			return up.updateMacSys, false
 		default:
-			return up.updateMacAppStore
+			return nil, false
 		}
 	case "freebsd":
-		return up.updateFreeBSD
+		return up.updateFreeBSD, true
 	}
-	return nil
+	return nil, false
 }
 
 // Update runs a single update attempt using the platform-specific mechanism.
@@ -201,8 +240,12 @@ func Update(args Arguments) error {
 }
 
 func (up *Updater) confirm(ver string) bool {
-	if version.Short() == ver {
-		up.Logf("already running %v; no update needed", ver)
+	switch cmpver.Compare(version.Short(), ver) {
+	case 0:
+		up.Logf("already running %v version %v; no update needed", up.track, ver)
+		return false
+	case 1:
+		up.Logf("installed %v version %v is newer than the latest available version %v; no update needed", up.track, version.Short(), ver)
 		return false
 	}
 	if up.Confirm != nil {
@@ -234,13 +277,14 @@ func (up *Updater) updateSynology() error {
 		return fmt.Errorf("cannot find Synology package for os=%s arch=%s, please report a bug with your device model", osName, arch)
 	}
 
-	if !up.confirm(latest.SPKsVersion) {
-		return nil
-	}
 	if err := requireRoot(); err != nil {
 		return err
 	}
+	if !up.confirm(latest.SPKsVersion) {
+		return nil
+	}
 
+	up.cleanupOldDownloads(filepath.Join(os.TempDir(), "tailscale-update*", "*.spk"))
 	// Download the SPK into a temporary directory.
 	spkDir, err := os.MkdirTemp("", "tailscale-update")
 	if err != nil {
@@ -256,9 +300,9 @@ func (up *Updater) updateSynology() error {
 	// connected over tailscale ssh and this parent process dies. Otherwise, if
 	// you abort synopkg install mid-way, tailscaled is not restarted.
 	cmd := exec.Command("nohup", "synopkg", "install", spkPath)
-	// Don't attach cmd.Stdout to os.Stdout because nohup will redirect that
-	// into nohup.out file. synopkg doesn't have any progress output anyway, it
-	// just spits out a JSON result when done.
+	// Don't attach cmd.Stdout to Stdout because nohup will redirect that into
+	// nohup.out file. synopkg doesn't have any progress output anyway, it just
+	// spits out a JSON result when done.
 	out, err := cmd.CombinedOutput()
 	if err != nil {
 		if dsmVersion == 6 && bytes.Contains(out, []byte("error = [290]")) {
@@ -369,15 +413,15 @@ func (up *Updater) updateDebLike() error {
 		// we're not updating them:
 		"-o", "APT::Get::List-Cleanup=0",
 	)
-	cmd.Stdout = os.Stdout
-	cmd.Stderr = os.Stderr
+	cmd.Stdout = up.Stdout
+	cmd.Stderr = up.Stderr
 	if err := cmd.Run(); err != nil {
 		return err
 	}
 
 	cmd = exec.Command("apt-get", "install", "--yes", "--allow-downgrades", "tailscale="+ver)
-	cmd.Stdout = os.Stdout
-	cmd.Stderr = os.Stderr
+	cmd.Stdout = up.Stdout
+	cmd.Stderr = up.Stderr
 	if err := cmd.Run(); err != nil {
 		return err
 	}
@@ -442,12 +486,12 @@ func updateDebianAptSourcesListBytes(was []byte, dstTrack string) (newContent []
 	return buf.Bytes(), nil
 }
 
+func (up *Updater) archPackageInstalled() bool {
+	err := exec.Command("pacman", "--query", "tailscale").Run()
+	return err == nil
+}
+
 func (up *Updater) updateArchLike() error {
-	if err := exec.Command("pacman", "--query", "tailscale").Run(); err != nil && isExitError(err) {
-		// Tailscale was not installed via pacman, update via tarball download
-		// instead.
-		return up.updateLinuxBinary()
-	}
 	// Arch maintainer asked us not to implement "tailscale update" or
 	// auto-updates on Arch-based distros:
 	// https://github.com/tailscale/tailscale/issues/6995#issuecomment-1687080106
@@ -491,8 +535,8 @@ func (up *Updater) updateFedoraLike(packageManager string) func() error {
 		}
 
 		cmd := exec.Command(packageManager, "install", "--assumeyes", fmt.Sprintf("tailscale-%s-1", ver))
-		cmd.Stdout = os.Stdout
-		cmd.Stderr = os.Stderr
+		cmd.Stdout = up.Stdout
+		cmd.Stderr = up.Stderr
 		if err := cmd.Run(); err != nil {
 			return err
 		}
@@ -577,8 +621,8 @@ func (up *Updater) updateAlpineLike() (err error) {
 	}
 
 	cmd := exec.Command("apk", "upgrade", "tailscale")
-	cmd.Stdout = os.Stdout
-	cmd.Stderr = os.Stderr
+	cmd.Stdout = up.Stdout
+	cmd.Stderr = up.Stderr
 	if err := cmd.Run(); err != nil {
 		return fmt.Errorf("failed tailscale update using apk: %w", err)
 	}
@@ -608,73 +652,64 @@ func (up *Updater) updateMacSys() error {
 }
 
 func (up *Updater) updateMacAppStore() error {
-	out, err := exec.Command("defaults", "read", "/Library/Preferences/com.apple.commerce.plist", "AutoUpdate").CombinedOutput()
+	// We can't trigger the update via App Store from the sandboxed app. At
+	// most, we can open the App Store page for them.
+	up.Logf("Please use the App Store to update Tailscale.\nConsider enabling Automatic Updates in the App Store Settings, if you haven't already.\nOpening the Tailscale app page...")
+
+	out, err := exec.Command("open", "https://apps.apple.com/us/app/tailscale/id1475387142").CombinedOutput()
 	if err != nil {
-		return fmt.Errorf("can't check App Store auto-update setting: %w, output: %q", err, string(out))
-	}
-	const on = "1\n"
-	if string(out) != on {
-		up.Logf("NOTE: Automatic updating for App Store apps is turned off. You can change this setting in System Settings (search for ‘update’).")
-	}
-
-	out, err = exec.Command("softwareupdate", "--list").CombinedOutput()
-	if err != nil {
-		return fmt.Errorf("can't check App Store for available updates: %w, output: %q", err, string(out))
-	}
-
-	newTailscale := parseSoftwareupdateList(out)
-	if newTailscale == "" {
-		up.Logf("no Tailscale update available")
-		return nil
-	}
-
-	newTailscaleVer := strings.TrimPrefix(newTailscale, "Tailscale-")
-	if !up.confirm(newTailscaleVer) {
-		return nil
-	}
-
-	cmd := exec.Command("sudo", "softwareupdate", "--install", newTailscale)
-	cmd.Stdout = os.Stdout
-	cmd.Stderr = os.Stderr
-	if err := cmd.Run(); err != nil {
-		return fmt.Errorf("can't install App Store update for Tailscale: %w", err)
+		return fmt.Errorf("can't open the Tailscale page in App Store: %w, output: %q", err, string(out))
 	}
 	return nil
 }
 
-var macOSAppStoreListPattern = regexp.MustCompile(`(?m)^\s+\*\s+Label:\s*(Tailscale-\d[\d\.]+)`)
-
-// parseSoftwareupdateList searches the output of `softwareupdate --list` on
-// Darwin and returns the matching Tailscale package label. If there is none,
-// returns the empty string.
-//
-// See TestParseSoftwareupdateList for example inputs.
-func parseSoftwareupdateList(stdout []byte) string {
-	matches := macOSAppStoreListPattern.FindSubmatch(stdout)
-	if len(matches) < 2 {
-		return ""
-	}
-	return string(matches[1])
-}
-
-// winMSIEnv is the environment variable that, if set, is the MSI file for the
-// update command to install. It's passed like this so we can stop the
-// tailscale.exe process from running before the msiexec process runs and tries
-// to overwrite ourselves.
-const winMSIEnv = "TS_UPDATE_WIN_MSI"
+const (
+	// winMSIEnv is the environment variable that, if set, is the MSI file for
+	// the update command to install. It's passed like this so we can stop the
+	// tailscale.exe process from running before the msiexec process runs and
+	// tries to overwrite ourselves.
+	winMSIEnv = "TS_UPDATE_WIN_MSI"
+	// winExePathEnv is the environment variable that is set along with
+	// winMSIEnv and carries the full path of the calling tailscale.exe binary.
+	// It is used to re-launch the GUI process (tailscale-ipn.exe) after
+	// install is complete.
+	winExePathEnv = "TS_UPDATE_WIN_EXE_PATH"
+)
 
 var (
-	verifyAuthenticode func(string) error // or nil on non-Windows
-	markTempFileFunc   func(string) error // or nil on non-Windows
+	verifyAuthenticode          func(string) error // or nil on non-Windows
+	markTempFileFunc            func(string) error // or nil on non-Windows
+	launchTailscaleAsWinGUIUser func(string) error // or nil on non-Windows
 )
 
 func (up *Updater) updateWindows() error {
 	if msi := os.Getenv(winMSIEnv); msi != "" {
+		// stdout/stderr from this part of the install could be lost since the
+		// parent tailscaled is replaced. Create a temp log file to have some
+		// output to debug with in case update fails.
+		close, err := up.switchOutputToFile()
+		if err != nil {
+			up.Logf("failed to create log file for installation: %v; proceeding with existing outputs", err)
+		} else {
+			defer close.Close()
+		}
+
 		up.Logf("installing %v ...", msi)
 		if err := up.installMSI(msi); err != nil {
 			up.Logf("MSI install failed: %v", err)
 			return err
 		}
+		up.Logf("relaunching tailscale-ipn.exe...")
+		exePath := os.Getenv(winExePathEnv)
+		if exePath == "" {
+			up.Logf("env var %q not passed to installer binary copy", winExePathEnv)
+			return fmt.Errorf("env var %q not passed to installer binary copy", winExePathEnv)
+		}
+		if err := launchTailscaleAsWinGUIUser(exePath); err != nil {
+			up.Logf("Failed to re-launch tailscale after update: %v", err)
+			return err
+		}
+
 		up.Logf("success.")
 		return nil
 	}
@@ -687,12 +722,17 @@ func (up *Updater) updateWindows() error {
 		arch = "x86"
 	}
 
+	if !winutil.IsCurrentProcessElevated() {
+		return errors.New(`update must be run as Administrator
+
+you can run the command prompt as Administrator one of these ways:
+* right-click cmd.exe, select 'Run as administrator'
+* press Windows+x, then press a
+* press Windows+r, type in "cmd", then press Ctrl+Shift+Enter`)
+	}
 	if !up.confirm(ver) {
 		return nil
 	}
-	if !winutil.IsCurrentProcessElevated() {
-		return errors.New("must be run as Administrator")
-	}
 
 	tsDir := filepath.Join(os.Getenv("ProgramData"), "Tailscale")
 	msiDir := filepath.Join(tsDir, "MSICache")
@@ -704,6 +744,7 @@ func (up *Updater) updateWindows() error {
 	if err := os.MkdirAll(msiDir, 0700); err != nil {
 		return err
 	}
+	up.cleanupOldDownloads(filepath.Join(msiDir, "*.msi"))
 	pkgsPath := fmt.Sprintf("%s/tailscale-setup-%s-%s.msi", up.track, ver, arch)
 	msiTarget := filepath.Join(msiDir, path.Base(pkgsPath))
 	if err := up.downloadURLToFile(pkgsPath, msiTarget); err != nil {
@@ -717,7 +758,7 @@ func (up *Updater) updateWindows() error {
 	up.Logf("authenticode verification succeeded")
 
 	up.Logf("making tailscale.exe copy to switch to...")
-	selfCopy, err := makeSelfCopy()
+	selfOrig, selfCopy, err := makeSelfCopy()
 	if err != nil {
 		return err
 	}
@@ -725,9 +766,9 @@ func (up *Updater) updateWindows() error {
 	up.Logf("running tailscale.exe copy for final install...")
 
 	cmd := exec.Command(selfCopy, "update")
-	cmd.Env = append(os.Environ(), winMSIEnv+"="+msiTarget)
-	cmd.Stdout = os.Stderr
-	cmd.Stderr = os.Stderr
+	cmd.Env = append(os.Environ(), winMSIEnv+"="+msiTarget, winExePathEnv+"="+selfOrig)
+	cmd.Stdout = up.Stderr
+	cmd.Stderr = up.Stderr
 	cmd.Stdin = os.Stdin
 	if err := cmd.Start(); err != nil {
 		return err
@@ -738,18 +779,44 @@ func (up *Updater) updateWindows() error {
 	panic("unreachable")
 }
 
+func (up *Updater) switchOutputToFile() (io.Closer, error) {
+	var logFilePath string
+	exePath, err := os.Executable()
+	if err != nil {
+		logFilePath = filepath.Join(os.TempDir(), "tailscale-updater.log")
+	} else {
+		logFilePath = strings.TrimSuffix(exePath, ".exe") + ".log"
+	}
+
+	up.Logf("writing update output to %q", logFilePath)
+	logFile, err := os.Create(logFilePath)
+	if err != nil {
+		return nil, err
+	}
+
+	up.Logf = func(m string, args ...any) {
+		fmt.Fprintf(logFile, m+"\n", args...)
+	}
+	up.Stdout = logFile
+	up.Stderr = logFile
+	return logFile, nil
+}
+
 func (up *Updater) installMSI(msi string) error {
 	var err error
 	for tries := 0; tries < 2; tries++ {
-		cmd := exec.Command("msiexec.exe", "/i", filepath.Base(msi), "/quiet", "/promptrestart", "/qn")
+		// TS_NOLAUNCH: don't automatically launch the app after install.
+		// We will launch it explicitly as the current GUI user afterwards.
+		cmd := exec.Command("msiexec.exe", "/i", filepath.Base(msi), "/quiet", "/promptrestart", "/qn", "TS_NOLAUNCH=true")
 		cmd.Dir = filepath.Dir(msi)
-		cmd.Stdout = os.Stdout
-		cmd.Stderr = os.Stderr
+		cmd.Stdout = up.Stdout
+		cmd.Stderr = up.Stderr
 		cmd.Stdin = os.Stdin
 		err = cmd.Run()
 		if err == nil {
 			break
 		}
+		up.Logf("Install attempt failed: %v", err)
 		uninstallVersion := version.Short()
 		if v := os.Getenv("TS_DEBUG_UNINSTALL_VERSION"); v != "" {
 			uninstallVersion = v
@@ -757,8 +824,8 @@ func (up *Updater) installMSI(msi string) error {
 		// Assume it's a downgrade, which msiexec won't permit. Uninstall our current version first.
 		up.Logf("Uninstalling current version %q for downgrade...", uninstallVersion)
 		cmd = exec.Command("msiexec.exe", "/x", msiUUIDForVersion(uninstallVersion), "/norestart", "/qn")
-		cmd.Stdout = os.Stdout
-		cmd.Stderr = os.Stderr
+		cmd.Stdout = up.Stdout
+		cmd.Stderr = up.Stderr
 		cmd.Stdin = os.Stdin
 		err = cmd.Run()
 		up.Logf("msiexec uninstall: %v", err)
@@ -766,6 +833,30 @@ func (up *Updater) installMSI(msi string) error {
 	return err
 }
 
+// cleanupOldDownloads removes all files matching glob (see filepath.Glob).
+// Only regular files are removed, so the glob must match specific files and
+// not directories.
+func (up *Updater) cleanupOldDownloads(glob string) {
+	matches, err := filepath.Glob(glob)
+	if err != nil {
+		up.Logf("cleaning up old downloads: %v", err)
+		return
+	}
+	for _, m := range matches {
+		s, err := os.Lstat(m)
+		if err != nil {
+			up.Logf("cleaning up old downloads: %v", err)
+			continue
+		}
+		if !s.Mode().IsRegular() {
+			continue
+		}
+		if err := os.Remove(m); err != nil {
+			up.Logf("cleaning up old downloads: %v", err)
+		}
+	}
+}
+
 func msiUUIDForVersion(ver string) string {
 	arch := runtime.GOARCH
 	if arch == "386" {
@@ -779,30 +870,30 @@ func msiUUIDForVersion(ver string) string {
 	return "{" + strings.ToUpper(uuid.NewSHA1(uuid.NameSpaceURL, []byte(msiURL)).String()) + "}"
 }
 
-func makeSelfCopy() (tmpPathExe string, err error) {
+func makeSelfCopy() (origPathExe, tmpPathExe string, err error) {
 	selfExe, err := os.Executable()
 	if err != nil {
-		return "", err
+		return "", "", err
 	}
 	f, err := os.Open(selfExe)
 	if err != nil {
-		return "", err
+		return "", "", err
 	}
 	defer f.Close()
 	f2, err := os.CreateTemp("", "tailscale-updater-*.exe")
 	if err != nil {
-		return "", err
+		return "", "", err
 	}
 	if f := markTempFileFunc; f != nil {
 		if err := f(f2.Name()); err != nil {
-			return "", err
+			return "", "", err
 		}
 	}
 	if _, err := io.Copy(f2, f); err != nil {
 		f2.Close()
-		return "", err
+		return "", "", err
 	}
-	return f2.Name(), f2.Close()
+	return selfExe, f2.Name(), f2.Close()
 }
 
 func (up *Updater) downloadURLToFile(pathSrc, fileDst string) (ret error) {
@@ -846,8 +937,8 @@ func (up *Updater) updateFreeBSD() (err error) {
 	}
 
 	cmd := exec.Command("pkg", "upgrade", "tailscale")
-	cmd.Stdout = os.Stdout
-	cmd.Stderr = os.Stderr
+	cmd.Stdout = up.Stdout
+	cmd.Stderr = up.Stderr
 	if err := cmd.Run(); err != nil {
 		return fmt.Errorf("failed tailscale update using pkg: %w", err)
 	}
@@ -859,13 +950,13 @@ func (up *Updater) updateLinuxBinary() error {
 	if err != nil {
 		return err
 	}
-	if !up.confirm(ver) {
-		return nil
-	}
 	// Root is needed to overwrite binaries and restart systemd unit.
 	if err := requireRoot(); err != nil {
 		return err
 	}
+	if !up.confirm(ver) {
+		return nil
+	}
 
 	dlPath, err := up.downloadLinuxTarball(ver)
 	if err != nil {
@@ -894,7 +985,7 @@ func (up *Updater) updateLinuxBinary() error {
 func (up *Updater) downloadLinuxTarball(ver string) (string, error) {
 	dlDir, err := os.UserCacheDir()
 	if err != nil {
-		return "", err
+		dlDir = os.TempDir()
 	}
 	dlDir = filepath.Join(dlDir, "tailscale-update")
 	if err := os.MkdirAll(dlDir, 0700); err != nil {

clientupdate/clientupdate_test.go

@@ -11,6 +11,8 @@ import (
 	"maps"
 	"os"
 	"path/filepath"
+	"slices"
+	"sort"
 	"strings"
 	"testing"
 )
@@ -84,84 +86,6 @@ func TestUpdateDebianAptSourcesListBytes(t *testing.T) {
 	}
 }
 
-func TestParseSoftwareupdateList(t *testing.T) {
-	tests := []struct {
-		name  string
-		input []byte
-		want  string
-	}{
-		{
-			name: "update-at-end-of-list",
-			input: []byte(`
-	 Software Update Tool
-
-	 Finding available software
-	 Software Update found the following new or updated software:
-			* Label: MacBookAirEFIUpdate2.4-2.4
-					 Title: MacBook Air EFI Firmware Update, Version: 2.4, Size: 3817K, Recommended: YES, Action: restart,
-			* Label: ProAppsQTCodecs-1.0
-					 Title: ProApps QuickTime codecs, Version: 1.0, Size: 968K, Recommended: YES,
-			* Label: Tailscale-1.23.4
-					 Title: The Tailscale VPN, Version: 1.23.4, Size: 1023K, Recommended: YES,
-`),
-			want: "Tailscale-1.23.4",
-		},
-		{
-			name: "update-in-middle-of-list",
-			input: []byte(`
-	 Software Update Tool
-
-	 Finding available software
-	 Software Update found the following new or updated software:
-			* Label: MacBookAirEFIUpdate2.4-2.4
-					 Title: MacBook Air EFI Firmware Update, Version: 2.4, Size: 3817K, Recommended: YES, Action: restart,
-			* Label: Tailscale-1.23.5000
-					 Title: The Tailscale VPN, Version: 1.23.4, Size: 1023K, Recommended: YES,
-			* Label: ProAppsQTCodecs-1.0
-					 Title: ProApps QuickTime codecs, Version: 1.0, Size: 968K, Recommended: YES,
-`),
-			want: "Tailscale-1.23.5000",
-		},
-		{
-			name: "update-not-in-list",
-			input: []byte(`
-	 Software Update Tool
-
-	 Finding available software
-	 Software Update found the following new or updated software:
-			* Label: MacBookAirEFIUpdate2.4-2.4
-					 Title: MacBook Air EFI Firmware Update, Version: 2.4, Size: 3817K, Recommended: YES, Action: restart,
-			* Label: ProAppsQTCodecs-1.0
-					 Title: ProApps QuickTime codecs, Version: 1.0, Size: 968K, Recommended: YES,
-`),
-			want: "",
-		},
-		{
-			name: "decoy-in-list",
-			input: []byte(`
-	 Software Update Tool
-
-	 Finding available software
-	 Software Update found the following new or updated software:
-			* Label: MacBookAirEFIUpdate2.4-2.4
-					 Title: MacBook Air EFI Firmware Update, Version: 2.4, Size: 3817K, Recommended: YES, Action: restart,
-			* Label: Malware-1.0
-					 Title: * Label: Tailscale-0.99.0, Version: 1.0, Size: 968K, Recommended: NOT REALLY TBH,
-`),
-			want: "",
-		},
-	}
-
-	for _, test := range tests {
-		t.Run(test.name, func(t *testing.T) {
-			got := parseSoftwareupdateList(test.input)
-			if test.want != got {
-				t.Fatalf("got %q, want %q", got, test.want)
-			}
-		})
-	}
-}
-
 func TestUpdateYUMRepoTrack(t *testing.T) {
 	tests := []struct {
 		desc    string
@@ -761,3 +685,113 @@ func TestWriteFileSymlink(t *testing.T) {
 		}
 	}
 }
+
+func TestCleanupOldDownloads(t *testing.T) {
+	tests := []struct {
+		desc     string
+		before   []string
+		symlinks map[string]string
+		glob     string
+		after    []string
+	}{
+		{
+			desc: "MSIs",
+			before: []string{
+				"MSICache/tailscale-1.0.0.msi",
+				"MSICache/tailscale-1.1.0.msi",
+				"MSICache/readme.txt",
+			},
+			glob: "MSICache/*.msi",
+			after: []string{
+				"MSICache/readme.txt",
+			},
+		},
+		{
+			desc: "SPKs",
+			before: []string{
+				"tmp/tailscale-update-1/tailscale-1.0.0.spk",
+				"tmp/tailscale-update-2/tailscale-1.1.0.spk",
+				"tmp/readme.txt",
+				"tmp/tailscale-update-3",
+				"tmp/tailscale-update-4/tailscale-1.3.0",
+			},
+			glob: "tmp/tailscale-update*/*.spk",
+			after: []string{
+				"tmp/readme.txt",
+				"tmp/tailscale-update-3",
+				"tmp/tailscale-update-4/tailscale-1.3.0",
+			},
+		},
+		{
+			desc:   "empty-target",
+			before: []string{},
+			glob:   "tmp/tailscale-update*/*.spk",
+			after:  []string{},
+		},
+		{
+			desc: "keep-dirs",
+			before: []string{
+				"tmp/tailscale-update-1/tailscale-1.0.0.spk",
+			},
+			glob: "tmp/tailscale-update*",
+			after: []string{
+				"tmp/tailscale-update-1/tailscale-1.0.0.spk",
+			},
+		},
+		{
+			desc: "no-follow-symlinks",
+			before: []string{
+				"MSICache/tailscale-1.0.0.msi",
+				"MSICache/tailscale-1.1.0.msi",
+				"MSICache/readme.txt",
+			},
+			symlinks: map[string]string{
+				"MSICache/tailscale-1.3.0.msi": "MSICache/tailscale-1.0.0.msi",
+				"MSICache/tailscale-1.4.0.msi": "MSICache/readme.txt",
+			},
+			glob: "MSICache/*.msi",
+			after: []string{
+				"MSICache/tailscale-1.3.0.msi",
+				"MSICache/tailscale-1.4.0.msi",
+				"MSICache/readme.txt",
+			},
+		},
+	}
+	for _, tt := range tests {
+		t.Run(tt.desc, func(t *testing.T) {
+			dir := t.TempDir()
+			for _, p := range tt.before {
+				if err := os.MkdirAll(filepath.Join(dir, filepath.Dir(p)), 0700); err != nil {
+					t.Fatal(err)
+				}
+				if err := os.WriteFile(filepath.Join(dir, p), []byte(tt.desc), 0600); err != nil {
+					t.Fatal(err)
+				}
+			}
+			for from, to := range tt.symlinks {
+				if err := os.Symlink(filepath.Join(dir, to), filepath.Join(dir, from)); err != nil {
+					t.Fatal(err)
+				}
+			}
+
+			up := &Updater{Arguments: Arguments{Logf: t.Logf}}
+			up.cleanupOldDownloads(filepath.Join(dir, tt.glob))
+
+			var after []string
+			if err := filepath.WalkDir(dir, func(path string, d fs.DirEntry, err error) error {
+				if !d.IsDir() {
+					after = append(after, strings.TrimPrefix(filepath.ToSlash(path), filepath.ToSlash(dir)+"/"))
+				}
+				return nil
+			}); err != nil {
+				t.Fatal(err)
+			}
+
+			sort.Strings(after)
+			sort.Strings(tt.after)
+			if !slices.Equal(after, tt.after) {
+				t.Errorf("got files after cleanup: %q, want: %q", after, tt.after)
+			}
+		})
+	}
+}

clientupdate/clientupdate_windows.go

@@ -7,13 +7,20 @@
 package clientupdate
 
 import (
+	"os/exec"
+	"os/user"
+	"path/filepath"
+	"syscall"
+
 	"golang.org/x/sys/windows"
+	"tailscale.com/util/winutil"
 	"tailscale.com/util/winutil/authenticode"
 )
 
 func init() {
 	markTempFileFunc = markTempFileWindows
 	verifyAuthenticode = verifyTailscale
+	launchTailscaleAsWinGUIUser = launchTailscaleAsGUIUser
 }
 
 func markTempFileWindows(name string) error {
@@ -26,3 +33,25 @@ const certSubjectTailscale = "Tailscale Inc."
 func verifyTailscale(path string) error {
 	return authenticode.Verify(path, certSubjectTailscale)
 }
+
+func launchTailscaleAsGUIUser(exePath string) error {
+	exePath = filepath.Join(filepath.Dir(exePath), "tailscale-ipn.exe")
+
+	var token windows.Token
+	if u, err := user.Current(); err == nil && u.Name == "SYSTEM" {
+		sessionID := winutil.WTSGetActiveConsoleSessionId()
+		if sessionID != 0xFFFFFFFF {
+			if err := windows.WTSQueryUserToken(sessionID, &token); err != nil {
+				return err
+			}
+			defer token.Close()
+		}
+	}
+
+	cmd := exec.Command(exePath)
+	cmd.SysProcAttr = &syscall.SysProcAttr{
+		Token:      syscall.Token(token),
+		HideWindow: true,
+	}
+	return cmd.Start()
+}

clientupdate/distsign/roots/distsign-prod-root-1-pub.pem

@@ -1,3 +1,3 @@
 -----BEGIN ROOT PUBLIC KEY-----
-Muw5GkO5mASsJ7k6kS+svfuanr6XcW9I7fPGtyqOTeI=
+ZjjKhUHBtLNRSO1dhOTjrXJGJ8lDe1594WM2XDuheVQ=
 -----END ROOT PUBLIC KEY-----

cmd/containerboot/main.go

@@ -19,8 +19,7 @@
 //   - TS_TAILNET_TARGET_IP: proxy all incoming non-Tailscale traffic to the given
 //     destination.
 //   - TS_TAILSCALED_EXTRA_ARGS: extra arguments to 'tailscaled'.
-//   - TS_EXTRA_ARGS: extra arguments to 'tailscale login', these are not
-//     reset on restart.
+//   - TS_EXTRA_ARGS: extra arguments to 'tailscale up'.
 //   - TS_USERSPACE: run with userspace networking (the default)
 //     instead of kernel networking.
 //   - TS_STATE_DIR: the directory in which to store tailscaled
@@ -36,15 +35,9 @@
 //   - TS_SOCKET: the path where the tailscaled LocalAPI socket should
 //     be created.
 //   - TS_AUTH_ONCE: if true, only attempt to log in if not already
-//     logged in. If false, forcibly log in every time the container starts.
-//     The default until 1.50.0 was false, but that was misleading: until
-//     1.50, containerboot used `tailscale up` which would ignore an authkey
-//     argument if there was already a node key. Effectively, this behaved
-//     as though TS_AUTH_ONCE were always true.
-//     In 1.50.0 the change was made to use `tailscale login` instead of `up`,
-//     and login will reauthenticate every time it is given an authkey.
-//     In 1.50.1 we set the TS_AUTH_ONCE to true, to match the previously
-//     observed behavior.
+//     logged in. If false (the default, for backwards
+//     compatibility), forcibly log in every time the
+//     container starts.
 //   - TS_SERVE_CONFIG: if specified, is the file path where the ipn.ServeConfig is located.
 //     It will be applied once tailscaled is up and running. If the file contains
 //     ${TS_CERT_DOMAIN}, it will be replaced with the value of the available FQDN.
@@ -84,10 +77,19 @@ import (
 	"golang.org/x/sys/unix"
 	"tailscale.com/client/tailscale"
 	"tailscale.com/ipn"
+	"tailscale.com/types/logger"
 	"tailscale.com/types/ptr"
 	"tailscale.com/util/deephash"
+	"tailscale.com/util/linuxfw"
 )
 
+func newNetfilterRunner(logf logger.Logf) (linuxfw.NetfilterRunner, error) {
+	if defaultBool("TS_TEST_FAKE_NETFILTER", false) {
+		return linuxfw.NewFakeIPTablesRunner(), nil
+	}
+	return linuxfw.New(logf)
+}
+
 func main() {
 	log.SetPrefix("boot: ")
 	tailscale.I_Acknowledge_This_API_Is_Unstable = true
@@ -109,7 +111,7 @@ func main() {
 		SOCKSProxyAddr:  defaultEnv("TS_SOCKS5_SERVER", ""),
 		HTTPProxyAddr:   defaultEnv("TS_OUTBOUND_HTTP_PROXY_LISTEN", ""),
 		Socket:          defaultEnv("TS_SOCKET", "/tmp/tailscaled.sock"),
-		AuthOnce:        defaultBool("TS_AUTH_ONCE", true),
+		AuthOnce:        defaultBool("TS_AUTH_ONCE", false),
 		Root:            defaultEnv("TS_TEST_ONLY_ROOT", "/"),
 	}
 
@@ -203,7 +205,7 @@ func main() {
 		}
 		didLogin = true
 		w.Close()
-		if err := tailscaleLogin(bootCtx, cfg); err != nil {
+		if err := tailscaleUp(bootCtx, cfg); err != nil {
 			return fmt.Errorf("failed to auth tailscale: %v", err)
 		}
 		w, err = client.WatchIPNBus(bootCtx, ipn.NotifyInitialNetMap|ipn.NotifyInitialState)
@@ -253,10 +255,12 @@ authLoop:
 	ctx, cancel := context.WithCancel(context.Background()) // no deadline now that we're in steady state
 	defer cancel()
 
-	// 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)
+	if cfg.AuthOnce {
+		// 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)
+		}
 	}
 
 	if cfg.ServeConfigPath != "" {
@@ -295,6 +299,13 @@ authLoop:
 	if cfg.ServeConfigPath != "" {
 		go watchServeConfigChanges(ctx, cfg.ServeConfigPath, certDomainChanged, certDomain, client)
 	}
+	var nfr linuxfw.NetfilterRunner
+	if wantProxy {
+		nfr, err = newNetfilterRunner(log.Printf)
+		if err != nil {
+			log.Fatalf("error creating new netfilter runner: %v", err)
+		}
+	}
 	for {
 		n, err := w.Next()
 		if err != nil {
@@ -315,7 +326,7 @@ authLoop:
 			ipsHaveChanged := newCurrentIPs != currentIPs
 			if cfg.ProxyTo != "" && len(addrs) > 0 && ipsHaveChanged {
 				log.Printf("Installing proxy rules")
-				if err := installIngressForwardingRule(ctx, cfg.ProxyTo, addrs); err != nil {
+				if err := installIngressForwardingRule(ctx, cfg.ProxyTo, addrs, nfr); err != nil {
 					log.Fatalf("installing ingress proxy rules: %v", err)
 				}
 			}
@@ -330,7 +341,7 @@ authLoop:
 				}
 			}
 			if cfg.TailnetTargetIP != "" && ipsHaveChanged && len(addrs) > 0 {
-				if err := installEgressForwardingRule(ctx, cfg.TailnetTargetIP, addrs); err != nil {
+				if err := installEgressForwardingRule(ctx, cfg.TailnetTargetIP, addrs, nfr); err != nil {
 					log.Fatalf("installing egress proxy rules: %v", err)
 				}
 			}
@@ -385,19 +396,20 @@ func watchServeConfigChanges(ctx context.Context, path string, cdChanged <-chan
 		panic("cd must not be nil")
 	}
 	var tickChan <-chan time.Time
-	w, err := fsnotify.NewWatcher()
-	if err != nil {
+	var eventChan <-chan fsnotify.Event
+	if w, err := fsnotify.NewWatcher(); err != nil {
 		log.Printf("failed to create fsnotify watcher, timer-only mode: %v", err)
 		ticker := time.NewTicker(5 * time.Second)
 		defer ticker.Stop()
 		tickChan = ticker.C
 	} else {
 		defer w.Close()
+		if err := w.Add(filepath.Dir(path)); err != nil {
+			log.Fatalf("failed to add fsnotify watch: %v", err)
+		}
+		eventChan = w.Events
 	}
 
-	if err := w.Add(filepath.Dir(path)); err != nil {
-		log.Fatalf("failed to add fsnotify watch: %v", err)
-	}
 	var certDomain string
 	var prevServeConfig *ipn.ServeConfig
 	for {
@@ -407,7 +419,7 @@ func watchServeConfigChanges(ctx context.Context, path string, cdChanged <-chan
 		case <-cdChanged:
 			certDomain = *certDomainAtomic.Load()
 		case <-tickChan:
-		case <-w.Events:
+		case <-eventChan:
 			// We can't do any reasonable filtering on the event because of how
 			// k8s handles these mounts. So just re-read the file and apply it
 			// if it's changed.
@@ -528,29 +540,40 @@ func tailscaledArgs(cfg *settings) []string {
 	return args
 }
 
-// tailscaleLogin uses cfg to run 'tailscale login' everytime containerboot
-// starts, or if TS_AUTH_ONCE is set, only the first time containerboot starts.
-func tailscaleLogin(ctx context.Context, cfg *settings) error {
-	args := []string{"--socket=" + cfg.Socket, "login"}
+// tailscaleUp uses cfg to run 'tailscale up' everytime containerboot starts, or
+// if TS_AUTH_ONCE is set, only the first time containerboot starts.
+func tailscaleUp(ctx context.Context, cfg *settings) error {
+	args := []string{"--socket=" + cfg.Socket, "up"}
+	if cfg.AcceptDNS {
+		args = append(args, "--accept-dns=true")
+	} else {
+		args = append(args, "--accept-dns=false")
+	}
 	if cfg.AuthKey != "" {
 		args = append(args, "--authkey="+cfg.AuthKey)
 	}
+	if cfg.Routes != "" {
+		args = append(args, "--advertise-routes="+cfg.Routes)
+	}
+	if cfg.Hostname != "" {
+		args = append(args, "--hostname="+cfg.Hostname)
+	}
 	if cfg.ExtraArgs != "" {
 		args = append(args, strings.Fields(cfg.ExtraArgs)...)
 	}
-	log.Printf("Running 'tailscale login'")
+	log.Printf("Running 'tailscale up'")
 	cmd := exec.CommandContext(ctx, "tailscale", args...)
 	cmd.Stdout = os.Stdout
 	cmd.Stderr = os.Stderr
 	if err := cmd.Run(); err != nil {
-		return fmt.Errorf("tailscale login failed: %v", err)
+		return fmt.Errorf("tailscale up failed: %v", err)
 	}
 	return nil
 }
 
 // tailscaleSet uses cfg to run 'tailscale set' to set any known configuration
 // options that are passed in via environment variables. This is run after the
-// node is in Running state.
+// node is in Running state and only if TS_AUTH_ONCE is set.
 func tailscaleSet(ctx context.Context, cfg *settings) error {
 	args := []string{"--socket=" + cfg.Socket, "set"}
 	if cfg.AcceptDNS {
@@ -662,16 +685,12 @@ func ensureIPForwarding(root, clusterProxyTarget, tailnetTargetiP, routes string
 	return nil
 }
 
-func installEgressForwardingRule(ctx context.Context, dstStr string, tsIPs []netip.Prefix) error {
+func installEgressForwardingRule(ctx context.Context, dstStr string, tsIPs []netip.Prefix, nfr linuxfw.NetfilterRunner) error {
 	dst, err := netip.ParseAddr(dstStr)
 	if err != nil {
 		return err
 	}
-	argv0 := "iptables"
-	if dst.Is6() {
-		argv0 = "ip6tables"
-	}
-	var local string
+	var local netip.Addr
 	for _, pfx := range tsIPs {
 		if !pfx.IsSingleIP() {
 			continue
@@ -679,52 +698,30 @@ func installEgressForwardingRule(ctx context.Context, dstStr string, tsIPs []net
 		if pfx.Addr().Is4() != dst.Is4() {
 			continue
 		}
-		local = pfx.Addr().String()
+		local = pfx.Addr()
 		break
 	}
-	if local == "" {
+	if !local.IsValid() {
 		return fmt.Errorf("no tailscale IP matching family of %s found in %v", dstStr, tsIPs)
 	}
-	// Technically, if the control server ever changes the IPs assigned to this
-	// node, we'll slowly accumulate iptables rules. This shouldn't happen, so
-	// for now we'll live with it.
-	// Set up a rule that ensures that all packets
-	// except for those received on tailscale0 interface is forwarded to
-	// destination address
-	cmdDNAT := exec.CommandContext(ctx, argv0, "-t", "nat", "-I", "PREROUTING", "1", "!", "-i", "tailscale0", "-j", "DNAT", "--to-destination", dstStr)
-	cmdDNAT.Stdout = os.Stdout
-	cmdDNAT.Stderr = os.Stderr
-	if err := cmdDNAT.Run(); err != nil {
-		return fmt.Errorf("executing iptables failed: %w", err)
+	if err := nfr.DNATNonTailscaleTraffic("tailscale0", dst); err != nil {
+		return fmt.Errorf("installing egress proxy rules: %w", err)
 	}
-	// Set up a rule that ensures that all packets sent to the destination
-	// address will have the proxy's IP set as source IP
-	cmdSNAT := exec.CommandContext(ctx, argv0, "-t", "nat", "-I", "POSTROUTING", "1", "--destination", dstStr, "-j", "SNAT", "--to-source", local)
-	cmdSNAT.Stdout = os.Stdout
-	cmdSNAT.Stderr = os.Stderr
-	if err := cmdSNAT.Run(); err != nil {
-		return fmt.Errorf("setting up SNAT via iptables failed: %w", err)
+	if err := nfr.AddSNATRuleForDst(local, dst); err != nil {
+		return fmt.Errorf("installing egress proxy rules: %w", err)
 	}
-
-	cmdClamp := exec.CommandContext(ctx, argv0, "-t", "mangle", "-A", "FORWARD", "-o", "tailscale0", "-p", "tcp", "-m", "tcp", "--tcp-flags", "SYN,RST", "SYN", "-j", "TCPMSS", "--clamp-mss-to-pmtu")
-	cmdClamp.Stdout = os.Stdout
-	cmdClamp.Stderr = os.Stderr
-	if err := cmdClamp.Run(); err != nil {
-		return fmt.Errorf("executing iptables failed: %w", err)
+	if err := nfr.ClampMSSToPMTU("tailscale0", dst); err != nil {
+		return fmt.Errorf("installing egress proxy rules: %w", err)
 	}
 	return nil
 }
 
-func installIngressForwardingRule(ctx context.Context, dstStr string, tsIPs []netip.Prefix) error {
+func installIngressForwardingRule(ctx context.Context, dstStr string, tsIPs []netip.Prefix, nfr linuxfw.NetfilterRunner) error {
 	dst, err := netip.ParseAddr(dstStr)
 	if err != nil {
 		return err
 	}
-	argv0 := "iptables"
-	if dst.Is6() {
-		argv0 = "ip6tables"
-	}
-	var local string
+	var local netip.Addr
 	for _, pfx := range tsIPs {
 		if !pfx.IsSingleIP() {
 			continue
@@ -732,26 +729,17 @@ func installIngressForwardingRule(ctx context.Context, dstStr string, tsIPs []ne
 		if pfx.Addr().Is4() != dst.Is4() {
 			continue
 		}
-		local = pfx.Addr().String()
+		local = pfx.Addr()
 		break
 	}
-	if local == "" {
+	if !local.IsValid() {
 		return fmt.Errorf("no tailscale IP matching family of %s found in %v", dstStr, tsIPs)
 	}
-	// Technically, if the control server ever changes the IPs assigned to this
-	// node, we'll slowly accumulate iptables rules. This shouldn't happen, so
-	// for now we'll live with it.
-	cmd := exec.CommandContext(ctx, argv0, "-t", "nat", "-I", "PREROUTING", "1", "-d", local, "-j", "DNAT", "--to-destination", dstStr)
-	cmd.Stdout = os.Stdout
-	cmd.Stderr = os.Stderr
-	if err := cmd.Run(); err != nil {
-		return fmt.Errorf("executing iptables failed: %w", err)
+	if err := nfr.AddDNATRule(local, dst); err != nil {
+		return fmt.Errorf("installing ingress proxy rules: %w", err)
 	}
-	cmdClamp := exec.CommandContext(ctx, argv0, "-t", "mangle", "-A", "FORWARD", "-o", "tailscale0", "-p", "tcp", "-m", "tcp", "--tcp-flags", "SYN,RST", "SYN", "-j", "TCPMSS", "--clamp-mss-to-pmtu")
-	cmdClamp.Stdout = os.Stdout
-	cmdClamp.Stderr = os.Stderr
-	if err := cmdClamp.Run(); err != nil {
-		return fmt.Errorf("executing iptables failed: %w", err)
+	if err := nfr.ClampMSSToPMTU("tailscale0", dst); err != nil {
+		return fmt.Errorf("installing ingress proxy rules: %w", err)
 	}
 	return nil
 }

cmd/containerboot/main_test.go

@@ -129,22 +129,16 @@ func TestContainerBoot(t *testing.T) {
 		{
 			// Out of the box default: runs in userspace mode, ephemeral storage, interactive login.
 			Name: "no_args",
-			Env: map[string]string{
-				"TS_AUTH_ONCE": "false",
-			},
-
+			Env:  nil,
 			Phases: []phase{
 				{
 					WantCmds: []string{
 						"/usr/bin/tailscaled --socket=/tmp/tailscaled.sock --state=mem: --statedir=/tmp --tun=userspace-networking",
-						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock login",
+						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock up --accept-dns=false",
 					},
 				},
 				{
 					Notify: runningNotify,
-					WantCmds: []string{
-						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock set --accept-dns=false",
-					},
 				},
 			},
 		},
@@ -152,21 +146,17 @@ func TestContainerBoot(t *testing.T) {
 			// Userspace mode, ephemeral storage, authkey provided on every run.
 			Name: "authkey",
 			Env: map[string]string{
-				"TS_AUTHKEY":   "tskey-key",
-				"TS_AUTH_ONCE": "false",
+				"TS_AUTHKEY": "tskey-key",
 			},
 			Phases: []phase{
 				{
 					WantCmds: []string{
 						"/usr/bin/tailscaled --socket=/tmp/tailscaled.sock --state=mem: --statedir=/tmp --tun=userspace-networking",
-						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock login --authkey=tskey-key",
+						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock up --accept-dns=false --authkey=tskey-key",
 					},
 				},
 				{
 					Notify: runningNotify,
-					WantCmds: []string{
-						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock set --accept-dns=false",
-					},
 				},
 			},
 		},
@@ -174,21 +164,17 @@ func TestContainerBoot(t *testing.T) {
 			// Userspace mode, ephemeral storage, authkey provided on every run.
 			Name: "authkey-old-flag",
 			Env: map[string]string{
-				"TS_AUTH_KEY":  "tskey-key",
-				"TS_AUTH_ONCE": "false",
+				"TS_AUTH_KEY": "tskey-key",
 			},
 			Phases: []phase{
 				{
 					WantCmds: []string{
 						"/usr/bin/tailscaled --socket=/tmp/tailscaled.sock --state=mem: --statedir=/tmp --tun=userspace-networking",
-						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock login --authkey=tskey-key",
+						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock up --accept-dns=false --authkey=tskey-key",
 					},
 				},
 				{
 					Notify: runningNotify,
-					WantCmds: []string{
-						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock set --accept-dns=false",
-					},
 				},
 			},
 		},
@@ -197,35 +183,30 @@ func TestContainerBoot(t *testing.T) {
 			Env: map[string]string{
 				"TS_AUTHKEY":   "tskey-key",
 				"TS_STATE_DIR": filepath.Join(d, "tmp"),
-				"TS_AUTH_ONCE": "false",
 			},
 			Phases: []phase{
 				{
 					WantCmds: []string{
 						"/usr/bin/tailscaled --socket=/tmp/tailscaled.sock --statedir=/tmp --tun=userspace-networking",
-						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock login --authkey=tskey-key",
+						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock up --accept-dns=false --authkey=tskey-key",
 					},
 				},
 				{
 					Notify: runningNotify,
-					WantCmds: []string{
-						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock set --accept-dns=false",
-					},
 				},
 			},
 		},
 		{
 			Name: "routes",
 			Env: map[string]string{
-				"TS_AUTHKEY":   "tskey-key",
-				"TS_ROUTES":    "1.2.3.0/24,10.20.30.0/24",
-				"TS_AUTH_ONCE": "false",
+				"TS_AUTHKEY": "tskey-key",
+				"TS_ROUTES":  "1.2.3.0/24,10.20.30.0/24",
 			},
 			Phases: []phase{
 				{
 					WantCmds: []string{
 						"/usr/bin/tailscaled --socket=/tmp/tailscaled.sock --state=mem: --statedir=/tmp --tun=userspace-networking",
-						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock login --authkey=tskey-key",
+						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock up --accept-dns=false --authkey=tskey-key --advertise-routes=1.2.3.0/24,10.20.30.0/24",
 					},
 				},
 				{
@@ -234,9 +215,6 @@ func TestContainerBoot(t *testing.T) {
 						"proc/sys/net/ipv4/ip_forward":          "0",
 						"proc/sys/net/ipv6/conf/all/forwarding": "0",
 					},
-					WantCmds: []string{
-						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock set --accept-dns=false --advertise-routes=1.2.3.0/24,10.20.30.0/24",
-					},
 				},
 			},
 		},
@@ -246,13 +224,12 @@ func TestContainerBoot(t *testing.T) {
 				"TS_AUTHKEY":   "tskey-key",
 				"TS_ROUTES":    "1.2.3.0/24,10.20.30.0/24",
 				"TS_USERSPACE": "false",
-				"TS_AUTH_ONCE": "false",
 			},
 			Phases: []phase{
 				{
 					WantCmds: []string{
 						"/usr/bin/tailscaled --socket=/tmp/tailscaled.sock --state=mem: --statedir=/tmp",
-						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock login --authkey=tskey-key",
+						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock up --accept-dns=false --authkey=tskey-key --advertise-routes=1.2.3.0/24,10.20.30.0/24",
 					},
 				},
 				{
@@ -261,9 +238,6 @@ func TestContainerBoot(t *testing.T) {
 						"proc/sys/net/ipv4/ip_forward":          "1",
 						"proc/sys/net/ipv6/conf/all/forwarding": "0",
 					},
-					WantCmds: []string{
-						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock set --accept-dns=false --advertise-routes=1.2.3.0/24,10.20.30.0/24",
-					},
 				},
 			},
 		},
@@ -273,13 +247,12 @@ func TestContainerBoot(t *testing.T) {
 				"TS_AUTHKEY":   "tskey-key",
 				"TS_ROUTES":    "::/64,1::/64",
 				"TS_USERSPACE": "false",
-				"TS_AUTH_ONCE": "false",
 			},
 			Phases: []phase{
 				{
 					WantCmds: []string{
 						"/usr/bin/tailscaled --socket=/tmp/tailscaled.sock --state=mem: --statedir=/tmp",
-						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock login --authkey=tskey-key",
+						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock up --accept-dns=false --authkey=tskey-key --advertise-routes=::/64,1::/64",
 					},
 				},
 				{
@@ -288,9 +261,6 @@ func TestContainerBoot(t *testing.T) {
 						"proc/sys/net/ipv4/ip_forward":          "0",
 						"proc/sys/net/ipv6/conf/all/forwarding": "1",
 					},
-					WantCmds: []string{
-						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock set --accept-dns=false --advertise-routes=::/64,1::/64",
-					},
 				},
 			},
 		},
@@ -300,13 +270,12 @@ func TestContainerBoot(t *testing.T) {
 				"TS_AUTHKEY":   "tskey-key",
 				"TS_ROUTES":    "::/64,1.2.3.0/24",
 				"TS_USERSPACE": "false",
-				"TS_AUTH_ONCE": "false",
 			},
 			Phases: []phase{
 				{
 					WantCmds: []string{
 						"/usr/bin/tailscaled --socket=/tmp/tailscaled.sock --state=mem: --statedir=/tmp",
-						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock login --authkey=tskey-key",
+						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock up --accept-dns=false --authkey=tskey-key --advertise-routes=::/64,1.2.3.0/24",
 					},
 				},
 				{
@@ -315,9 +284,6 @@ func TestContainerBoot(t *testing.T) {
 						"proc/sys/net/ipv4/ip_forward":          "1",
 						"proc/sys/net/ipv6/conf/all/forwarding": "1",
 					},
-					WantCmds: []string{
-						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock set --accept-dns=false --advertise-routes=::/64,1.2.3.0/24",
-					},
 				},
 			},
 		},
@@ -327,22 +293,16 @@ func TestContainerBoot(t *testing.T) {
 				"TS_AUTHKEY":   "tskey-key",
 				"TS_DEST_IP":   "1.2.3.4",
 				"TS_USERSPACE": "false",
-				"TS_AUTH_ONCE": "false",
 			},
 			Phases: []phase{
 				{
 					WantCmds: []string{
 						"/usr/bin/tailscaled --socket=/tmp/tailscaled.sock --state=mem: --statedir=/tmp",
-						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock login --authkey=tskey-key",
+						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock up --accept-dns=false --authkey=tskey-key",
 					},
 				},
 				{
 					Notify: runningNotify,
-					WantCmds: []string{
-						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock set --accept-dns=false",
-						"/usr/bin/iptables -t nat -I PREROUTING 1 -d 100.64.0.1 -j DNAT --to-destination 1.2.3.4",
-						"/usr/bin/iptables -t mangle -A FORWARD -o tailscale0 -p tcp -m tcp --tcp-flags SYN,RST SYN -j TCPMSS --clamp-mss-to-pmtu",
-					},
 				},
 			},
 		},
@@ -352,23 +312,16 @@ func TestContainerBoot(t *testing.T) {
 				"TS_AUTHKEY":           "tskey-key",
 				"TS_TAILNET_TARGET_IP": "100.99.99.99",
 				"TS_USERSPACE":         "false",
-				"TS_AUTH_ONCE":         "false",
 			},
 			Phases: []phase{
 				{
 					WantCmds: []string{
 						"/usr/bin/tailscaled --socket=/tmp/tailscaled.sock --state=mem: --statedir=/tmp",
-						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock login --authkey=tskey-key",
+						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock up --accept-dns=false --authkey=tskey-key",
 					},
 				},
 				{
 					Notify: runningNotify,
-					WantCmds: []string{
-						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock set --accept-dns=false",
-						"/usr/bin/iptables -t nat -I PREROUTING 1 ! -i tailscale0 -j DNAT --to-destination 100.99.99.99",
-						"/usr/bin/iptables -t nat -I POSTROUTING 1 --destination 100.99.99.99 -j SNAT --to-source 100.64.0.1",
-						"/usr/bin/iptables -t mangle -A FORWARD -o tailscale0 -p tcp -m tcp --tcp-flags SYN,RST SYN -j TCPMSS --clamp-mss-to-pmtu",
-					},
 				},
 			},
 		},
@@ -389,7 +342,7 @@ func TestContainerBoot(t *testing.T) {
 						State: ptr.To(ipn.NeedsLogin),
 					},
 					WantCmds: []string{
-						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock login --authkey=tskey-key",
+						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock up --accept-dns=false --authkey=tskey-key",
 					},
 				},
 				{
@@ -405,7 +358,6 @@ func TestContainerBoot(t *testing.T) {
 			Env: map[string]string{
 				"KUBERNETES_SERVICE_HOST":       kube.Host,
 				"KUBERNETES_SERVICE_PORT_HTTPS": kube.Port,
-				"TS_AUTH_ONCE":                  "false",
 			},
 			KubeSecret: map[string]string{
 				"authkey": "tskey-key",
@@ -414,7 +366,7 @@ func TestContainerBoot(t *testing.T) {
 				{
 					WantCmds: []string{
 						"/usr/bin/tailscaled --socket=/tmp/tailscaled.sock --state=kube:tailscale --statedir=/tmp --tun=userspace-networking",
-						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock login --authkey=tskey-key",
+						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock up --accept-dns=false --authkey=tskey-key",
 					},
 					WantKubeSecret: map[string]string{
 						"authkey": "tskey-key",
@@ -422,9 +374,6 @@ func TestContainerBoot(t *testing.T) {
 				},
 				{
 					Notify: runningNotify,
-					WantCmds: []string{
-						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock set --accept-dns=false",
-					},
 					WantKubeSecret: map[string]string{
 						"authkey":     "tskey-key",
 						"device_fqdn": "test-node.test.ts.net",
@@ -443,22 +392,18 @@ func TestContainerBoot(t *testing.T) {
 				"TS_KUBE_SECRET": "",
 				"TS_STATE_DIR":   filepath.Join(d, "tmp"),
 				"TS_AUTHKEY":     "tskey-key",
-				"TS_AUTH_ONCE":   "false",
 			},
 			KubeSecret: map[string]string{},
 			Phases: []phase{
 				{
 					WantCmds: []string{
 						"/usr/bin/tailscaled --socket=/tmp/tailscaled.sock --statedir=/tmp --tun=userspace-networking",
-						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock login --authkey=tskey-key",
+						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock up --accept-dns=false --authkey=tskey-key",
 					},
 					WantKubeSecret: map[string]string{},
 				},
 				{
-					Notify: runningNotify,
-					WantCmds: []string{
-						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock set --accept-dns=false",
-					},
+					Notify:         runningNotify,
 					WantKubeSecret: map[string]string{},
 				},
 			},
@@ -469,7 +414,6 @@ func TestContainerBoot(t *testing.T) {
 				"KUBERNETES_SERVICE_HOST":       kube.Host,
 				"KUBERNETES_SERVICE_PORT_HTTPS": kube.Port,
 				"TS_AUTHKEY":                    "tskey-key",
-				"TS_AUTH_ONCE":                  "false",
 			},
 			KubeSecret:    map[string]string{},
 			KubeDenyPatch: true,
@@ -477,15 +421,12 @@ func TestContainerBoot(t *testing.T) {
 				{
 					WantCmds: []string{
 						"/usr/bin/tailscaled --socket=/tmp/tailscaled.sock --state=kube:tailscale --statedir=/tmp --tun=userspace-networking",
-						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock login --authkey=tskey-key",
+						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock up --accept-dns=false --authkey=tskey-key",
 					},
 					WantKubeSecret: map[string]string{},
 				},
 				{
-					Notify: runningNotify,
-					WantCmds: []string{
-						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock set --accept-dns=false",
-					},
+					Notify:         runningNotify,
 					WantKubeSecret: map[string]string{},
 				},
 			},
@@ -515,7 +456,7 @@ func TestContainerBoot(t *testing.T) {
 						State: ptr.To(ipn.NeedsLogin),
 					},
 					WantCmds: []string{
-						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock login --authkey=tskey-key",
+						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock up --accept-dns=false --authkey=tskey-key",
 					},
 					WantKubeSecret: map[string]string{
 						"authkey": "tskey-key",
@@ -539,7 +480,6 @@ func TestContainerBoot(t *testing.T) {
 			Env: map[string]string{
 				"KUBERNETES_SERVICE_HOST":       kube.Host,
 				"KUBERNETES_SERVICE_PORT_HTTPS": kube.Port,
-				"TS_AUTH_ONCE":                  "false",
 			},
 			KubeSecret: map[string]string{
 				"authkey": "tskey-key",
@@ -548,7 +488,7 @@ func TestContainerBoot(t *testing.T) {
 				{
 					WantCmds: []string{
 						"/usr/bin/tailscaled --socket=/tmp/tailscaled.sock --state=kube:tailscale --statedir=/tmp --tun=userspace-networking",
-						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock login --authkey=tskey-key",
+						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock up --accept-dns=false --authkey=tskey-key",
 					},
 					WantKubeSecret: map[string]string{
 						"authkey": "tskey-key",
@@ -556,9 +496,6 @@ func TestContainerBoot(t *testing.T) {
 				},
 				{
 					Notify: runningNotify,
-					WantCmds: []string{
-						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock set --accept-dns=false",
-					},
 					WantKubeSecret: map[string]string{
 						"authkey":     "tskey-key",
 						"device_fqdn": "test-node.test.ts.net",
@@ -591,20 +528,16 @@ func TestContainerBoot(t *testing.T) {
 			Env: map[string]string{
 				"TS_SOCKS5_SERVER":              "localhost:1080",
 				"TS_OUTBOUND_HTTP_PROXY_LISTEN": "localhost:8080",
-				"TS_AUTH_ONCE":                  "false",
 			},
 			Phases: []phase{
 				{
 					WantCmds: []string{
 						"/usr/bin/tailscaled --socket=/tmp/tailscaled.sock --state=mem: --statedir=/tmp --tun=userspace-networking --socks5-server=localhost:1080 --outbound-http-proxy-listen=localhost:8080",
-						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock login",
+						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock up --accept-dns=false",
 					},
 				},
 				{
 					Notify: runningNotify,
-					WantCmds: []string{
-						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock set --accept-dns=false",
-					},
 				},
 			},
 		},
@@ -612,20 +545,16 @@ func TestContainerBoot(t *testing.T) {
 			Name: "dns",
 			Env: map[string]string{
 				"TS_ACCEPT_DNS": "true",
-				"TS_AUTH_ONCE":  "false",
 			},
 			Phases: []phase{
 				{
 					WantCmds: []string{
 						"/usr/bin/tailscaled --socket=/tmp/tailscaled.sock --state=mem: --statedir=/tmp --tun=userspace-networking",
-						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock login",
+						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock up --accept-dns=true",
 					},
 				},
 				{
 					Notify: runningNotify,
-					WantCmds: []string{
-						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock set --accept-dns=true",
-					},
 				},
 			},
 		},
@@ -634,41 +563,31 @@ func TestContainerBoot(t *testing.T) {
 			Env: map[string]string{
 				"TS_EXTRA_ARGS":            "--widget=rotated",
 				"TS_TAILSCALED_EXTRA_ARGS": "--experiments=widgets",
-				"TS_AUTH_ONCE":             "false",
 			},
 			Phases: []phase{
 				{
 					WantCmds: []string{
 						"/usr/bin/tailscaled --socket=/tmp/tailscaled.sock --state=mem: --statedir=/tmp --tun=userspace-networking --experiments=widgets",
-						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock login --widget=rotated",
+						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock up --accept-dns=false --widget=rotated",
 					},
-				},
-				{
+				}, {
 					Notify: runningNotify,
-					WantCmds: []string{
-						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock set --accept-dns=false",
-					},
 				},
 			},
 		},
 		{
 			Name: "hostname",
 			Env: map[string]string{
-				"TS_HOSTNAME":  "my-server",
-				"TS_AUTH_ONCE": "false",
+				"TS_HOSTNAME": "my-server",
 			},
 			Phases: []phase{
 				{
 					WantCmds: []string{
 						"/usr/bin/tailscaled --socket=/tmp/tailscaled.sock --state=mem: --statedir=/tmp --tun=userspace-networking",
-						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock login",
+						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock up --accept-dns=false --hostname=my-server",
 					},
-				},
-				{
+				}, {
 					Notify: runningNotify,
-					WantCmds: []string{
-						"/usr/bin/tailscale --socket=/tmp/tailscaled.sock set --accept-dns=false --hostname=my-server",
-					},
 				},
 			},
 		},
@@ -694,6 +613,7 @@ func TestContainerBoot(t *testing.T) {
 				fmt.Sprintf("TS_TEST_SOCKET=%s", lapi.Path),
 				fmt.Sprintf("TS_SOCKET=%s", runningSockPath),
 				fmt.Sprintf("TS_TEST_ONLY_ROOT=%s", d),
+				fmt.Sprint("TS_TEST_FAKE_NETFILTER=true"),
 			}
 			for k, v := range test.Env {
 				cmd.Env = append(cmd.Env, fmt.Sprintf("%s=%s", k, v))

cmd/derper/depaware.txt

@@ -2,11 +2,6 @@ tailscale.com/cmd/derper dependencies: (generated by github.com/tailscale/depawa
 
         filippo.io/edwards25519                                      from github.com/hdevalence/ed25519consensus
         filippo.io/edwards25519/field                                from filippo.io/edwards25519
-   W 💣 github.com/Microsoft/go-winio                                from tailscale.com/safesocket
-   W 💣 github.com/Microsoft/go-winio/internal/fs                    from github.com/Microsoft/go-winio
-   W 💣 github.com/Microsoft/go-winio/internal/socket                from github.com/Microsoft/go-winio
-   W    github.com/Microsoft/go-winio/internal/stringbuffer          from github.com/Microsoft/go-winio/internal/fs
-   W    github.com/Microsoft/go-winio/pkg/guid                       from github.com/Microsoft/go-winio+
    W 💣 github.com/alexbrainman/sspi                                 from github.com/alexbrainman/sspi/internal/common+
    W    github.com/alexbrainman/sspi/internal/common                 from github.com/alexbrainman/sspi/negotiate
    W 💣 github.com/alexbrainman/sspi/negotiate                       from tailscale.com/net/tshttpproxy
@@ -17,7 +12,6 @@ tailscale.com/cmd/derper dependencies: (generated by github.com/tailscale/depawa
         github.com/fxamacker/cbor/v2                                 from tailscale.com/tka
         github.com/golang/groupcache/lru                             from tailscale.com/net/dnscache
         github.com/golang/protobuf/proto                             from github.com/matttproud/golang_protobuf_extensions/pbutil
-        github.com/google/btree                                      from gvisor.dev/gvisor/pkg/tcpip/header
    L    github.com/google/nftables                                   from tailscale.com/util/linuxfw
    L 💣 github.com/google/nftables/alignedbuff                       from github.com/google/nftables/xt
    L 💣 github.com/google/nftables/binaryutil                        from github.com/google/nftables+
@@ -44,6 +38,11 @@ tailscale.com/cmd/derper dependencies: (generated by github.com/tailscale/depawa
   LD    github.com/prometheus/procfs                                 from github.com/prometheus/client_golang/prometheus
   LD    github.com/prometheus/procfs/internal/fs                     from github.com/prometheus/procfs
   LD    github.com/prometheus/procfs/internal/util                   from github.com/prometheus/procfs
+   W 💣 github.com/tailscale/go-winio                                from tailscale.com/safesocket
+   W 💣 github.com/tailscale/go-winio/internal/fs                    from github.com/tailscale/go-winio
+   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+
    L 💣 github.com/tailscale/netlink                                 from tailscale.com/util/linuxfw
    L 💣 github.com/vishvananda/netlink/nl                            from github.com/tailscale/netlink
    L    github.com/vishvananda/netns                                 from github.com/tailscale/netlink+
@@ -79,22 +78,6 @@ tailscale.com/cmd/derper dependencies: (generated by github.com/tailscale/depawa
         google.golang.org/protobuf/runtime/protoimpl                 from github.com/golang/protobuf/proto+
         google.golang.org/protobuf/types/descriptorpb                from google.golang.org/protobuf/reflect/protodesc
         google.golang.org/protobuf/types/known/timestamppb           from github.com/prometheus/client_golang/prometheus+
-        gvisor.dev/gvisor/pkg/atomicbitops                           from gvisor.dev/gvisor/pkg/buffer+
-        gvisor.dev/gvisor/pkg/bits                                   from gvisor.dev/gvisor/pkg/buffer
-     💣 gvisor.dev/gvisor/pkg/buffer                                 from gvisor.dev/gvisor/pkg/tcpip+
-        gvisor.dev/gvisor/pkg/context                                from gvisor.dev/gvisor/pkg/refs
-     💣 gvisor.dev/gvisor/pkg/gohacks                                from gvisor.dev/gvisor/pkg/state/wire+
-        gvisor.dev/gvisor/pkg/linewriter                             from gvisor.dev/gvisor/pkg/log
-        gvisor.dev/gvisor/pkg/log                                    from gvisor.dev/gvisor/pkg/context+
-        gvisor.dev/gvisor/pkg/refs                                   from gvisor.dev/gvisor/pkg/buffer
-     💣 gvisor.dev/gvisor/pkg/state                                  from gvisor.dev/gvisor/pkg/atomicbitops+
-        gvisor.dev/gvisor/pkg/state/wire                             from gvisor.dev/gvisor/pkg/state
-     💣 gvisor.dev/gvisor/pkg/sync                                   from gvisor.dev/gvisor/pkg/atomicbitops+
-        gvisor.dev/gvisor/pkg/tcpip                                  from gvisor.dev/gvisor/pkg/tcpip/header+
-        gvisor.dev/gvisor/pkg/tcpip/checksum                         from gvisor.dev/gvisor/pkg/buffer+
-        gvisor.dev/gvisor/pkg/tcpip/header                           from tailscale.com/net/packet
-        gvisor.dev/gvisor/pkg/tcpip/seqnum                           from gvisor.dev/gvisor/pkg/tcpip/header
-        gvisor.dev/gvisor/pkg/waiter                                 from gvisor.dev/gvisor/pkg/context+
         nhooyr.io/websocket                                          from tailscale.com/cmd/derper+
         nhooyr.io/websocket/internal/errd                            from nhooyr.io/websocket
         nhooyr.io/websocket/internal/xsync                           from nhooyr.io/websocket
@@ -128,7 +111,7 @@ tailscale.com/cmd/derper dependencies: (generated by github.com/tailscale/depawa
      💣 tailscale.com/net/tshttpproxy                                from tailscale.com/derp/derphttp+
         tailscale.com/net/wsconn                                     from tailscale.com/cmd/derper+
         tailscale.com/paths                                          from tailscale.com/client/tailscale
-        tailscale.com/safesocket                                     from tailscale.com/client/tailscale
+     💣 tailscale.com/safesocket                                     from tailscale.com/client/tailscale
         tailscale.com/syncs                                          from tailscale.com/cmd/derper+
         tailscale.com/tailcfg                                        from tailscale.com/client/tailscale+
         tailscale.com/tka                                            from tailscale.com/client/tailscale+
@@ -164,10 +147,11 @@ tailscale.com/cmd/derper dependencies: (generated by github.com/tailscale/depawa
    L    tailscale.com/util/linuxfw                                   from tailscale.com/net/netns
         tailscale.com/util/mak                                       from tailscale.com/syncs+
         tailscale.com/util/multierr                                  from tailscale.com/health+
+        tailscale.com/util/nocasemaps                                from tailscale.com/types/ipproto
         tailscale.com/util/set                                       from tailscale.com/health+
         tailscale.com/util/singleflight                              from tailscale.com/net/dnscache
         tailscale.com/util/slicesx                                   from tailscale.com/cmd/derper+
-        tailscale.com/util/vizerror                                  from tailscale.com/tsweb
+        tailscale.com/util/vizerror                                  from tailscale.com/tsweb+
    W 💣 tailscale.com/util/winutil                                   from tailscale.com/hostinfo+
         tailscale.com/version                                        from tailscale.com/derp+
         tailscale.com/version/distro                                 from tailscale.com/hostinfo+

cmd/derper/derper_test.go

@@ -12,6 +12,7 @@ import (
 	"testing"
 
 	"tailscale.com/net/stun"
+	"tailscale.com/tstest/deptest"
 )
 
 func TestProdAutocertHostPolicy(t *testing.T) {
@@ -128,3 +129,14 @@ func TestNoContent(t *testing.T) {
 		})
 	}
 }
+
+func TestDeps(t *testing.T) {
+	deptest.DepChecker{
+		BadDeps: map[string]string{
+			"gvisor.dev/gvisor/pkg/buffer":       "https://github.com/tailscale/tailscale/issues/9756",
+			"gvisor.dev/gvisor/pkg/cpuid":        "https://github.com/tailscale/tailscale/issues/9756",
+			"gvisor.dev/gvisor/pkg/tcpip":        "https://github.com/tailscale/tailscale/issues/9756",
+			"gvisor.dev/gvisor/pkg/tcpip/header": "https://github.com/tailscale/tailscale/issues/9756",
+		},
+	}.Check(t)
+}

cmd/derper/mesh.go

@@ -41,6 +41,7 @@ func startMeshWithHost(s *derp.Server, host string) error {
 		return err
 	}
 	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) {

cmd/k8s-operator/deploy/chart/.helmignore

@@ -0,0 +1,23 @@
+# Patterns to ignore when building packages.
+# This supports shell glob matching, relative path matching, and
+# negation (prefixed with !). Only one pattern per line.
+.DS_Store
+# Common VCS dirs
+.git/
+.gitignore
+.bzr/
+.bzrignore
+.hg/
+.hgignore
+.svn/
+# Common backup files
+*.swp
+*.bak
+*.tmp
+*.orig
+*~
+# Various IDEs
+.project
+.idea/
+*.tmproj
+.vscode/

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

@@ -0,0 +1,29 @@
+# Copyright (c) Tailscale Inc & AUTHORS
+# SPDX-License-Identifier: BSD-3-Clause
+
+apiVersion: v2
+name: tailscale-operator
+description: A Helm chart for Tailscale Kubernetes operator
+home: https://github.com/tailscale/tailscale
+
+keywords:
+  - "tailscale"
+  - "vpn"
+  - "ingress"
+  - "egress"
+  - "wireguard"
+
+sources:
+- https://github.com/tailscale/tailscale
+
+type: application
+
+maintainers:
+  - name: tailscale-maintainers
+    url: https://tailscale.com/
+
+# version will be set to Tailscale repo tag (without 'v') at release time.
+version: 0.1.0
+
+# appVersion will be set to Tailscale repo tag at release time.
+appVersion: "unstable"

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

@@ -0,0 +1,26 @@
+# Copyright (c) Tailscale Inc & AUTHORS
+# SPDX-License-Identifier: BSD-3-Clause
+
+{{ if eq .Values.apiServerProxyConfig.mode "true" }}
+apiVersion: rbac.authorization.k8s.io/v1
+kind: ClusterRole
+metadata:
+  name: tailscale-auth-proxy
+rules:
+- apiGroups: [""]
+  resources: ["users", "groups"]
+  verbs: ["impersonate"]
+---
+apiVersion: rbac.authorization.k8s.io/v1
+kind: ClusterRoleBinding
+metadata:
+  name: tailscale-auth-proxy
+subjects:
+- kind: ServiceAccount
+  name: operator
+  namespace: {{ .Release.Namespace }}
+roleRef:
+  kind: ClusterRole
+  name: tailscale-auth-proxy
+  apiGroup: rbac.authorization.k8s.io
+{{ end }}

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

@@ -0,0 +1,90 @@
+# Copyright (c) Tailscale Inc & AUTHORS
+# SPDX-License-Identifier: BSD-3-Clause
+
+apiVersion: apps/v1
+kind: Deployment
+metadata:
+  name: operator
+  namespace: {{ .Release.Namespace }}
+spec:
+  replicas: 1
+  strategy:
+    type: Recreate
+  selector:
+    matchLabels:
+      app: operator
+  template:
+    metadata:
+      {{- with .Values.operatorConfig.podAnnotations }}
+      annotations:
+        {{- toYaml . | nindent 8 }}
+      {{- end }}
+      labels:
+        app: operator
+    spec:
+      {{- with .Values.imagePullSecrets }}
+      imagePullSecrets:
+        {{- toYaml . | nindent 8 }}
+      {{- end }}
+      serviceAccountName: operator
+      {{- with .Values.operatorConfig.podSecurityContext }}
+      securityContext:
+        {{- toYaml .Values.operatorConfig.podSecurityContext | nindent 8 }}
+      {{- end }}
+      volumes:
+      - name: oauth
+        secret:
+          secretName: operator-oauth
+      containers:
+        - name: operator
+          {{- with .Values.operatorConfig.securityContext }}
+          securityContext:
+            {{- toYaml . | nindent 12 }}
+          {{- end }}
+          {{- with .Values.operatorConfig.resources }}
+          resources:
+            {{- toYaml . | nindent 12 }}
+          {{- end }}
+          {{- $operatorTag:= printf ":%s" ( .Values.operatorConfig.image.tag | default .Chart.AppVersion )}}
+          image: {{ .Values.operatorConfig.image.repo }}{{- if .Values.operatorConfig.image.digest -}}{{ printf "@%s" .Values.operatorConfig.image.digest}}{{- else -}}{{ printf "%s" $operatorTag }}{{- end }}
+          imagePullPolicy: {{ .Values.operatorConfig.image.pullPolicy }}
+          env:
+            - name: OPERATOR_HOSTNAME
+              value: {{ .Values.operatorConfig.hostname }}
+            - name: OPERATOR_SECRET
+              value: operator
+            - name: OPERATOR_LOGGING
+              value: {{ .Values.operatorConfig.logging }}
+            - name: OPERATOR_NAMESPACE
+              valueFrom:
+                fieldRef:
+                  fieldPath: metadata.namespace
+            - name: CLIENT_ID_FILE
+              value: /oauth/client_id
+            - name: CLIENT_SECRET_FILE
+              value: /oauth/client_secret
+            {{- $proxyTag := printf ":%s" ( .Values.proxyConfig.image.tag | default .Chart.AppVersion )}}
+            - name: PROXY_IMAGE
+              value: {{ .Values.proxyConfig.image.repo }}{{- if .Values.proxyConfig.image.digest -}}{{ printf "@%s" .Values.proxyConfig.image.digest}}{{- else -}}{{ printf "%s" $proxyTag }}{{- end }}
+            - name: PROXY_TAGS
+              value: {{ .Values.proxyConfig.defaultTags }}
+            - name: APISERVER_PROXY
+              value: "{{ .Values.apiServerProxyConfig.mode }}"
+            - name: PROXY_FIREWALL_MODE
+              value: {{ .Values.proxyConfig.firewallMode }}
+          volumeMounts:
+          - name: oauth
+            mountPath: /oauth
+            readOnly: true
+      {{- with .Values.operatorConfig.nodeSelector }}
+      nodeSelector:
+        {{- toYaml . | nindent 8 }}
+      {{- end }}
+      {{- with .Values.operatorConfig.affinity }}
+      affinity:
+        {{- toYaml . | nindent 8 }}
+      {{- end }}
+      {{- with .Values.operatorConfig.tolerations }}
+      tolerations:
+        {{- toYaml . | nindent 8 }}
+      {{- end }}

cmd/k8s-operator/deploy/chart/templates/oauth-secret.yaml

@@ -0,0 +1,13 @@
+# Copyright (c) Tailscale Inc & AUTHORS
+# SPDX-License-Identifier: BSD-3-Clause
+
+{{ if and .Values.oauth .Values.oauth.clientId -}}
+apiVersion: v1
+kind: Secret
+metadata:
+  name: operator-oauth
+  namespace: {{ .Release.Namespace }}
+stringData:
+  client_id: {{ .Values.oauth.clientId }}
+  client_secret: {{ .Values.oauth.clientSecret }}
+{{- end -}}

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

@@ -0,0 +1,60 @@
+# Copyright (c) Tailscale Inc & AUTHORS
+# SPDX-License-Identifier: BSD-3-Clause
+
+apiVersion: v1
+kind: ServiceAccount
+metadata:
+  name: operator
+  namespace: {{ .Release.Namespace }}
+---
+apiVersion: rbac.authorization.k8s.io/v1
+kind: ClusterRole
+metadata:
+  name: tailscale-operator
+rules:
+- apiGroups: [""]
+  resources: ["events", "services", "services/status"]
+  verbs: ["*"]
+- apiGroups: ["networking.k8s.io"]
+  resources: ["ingresses", "ingresses/status"]
+  verbs: ["*"]
+---
+apiVersion: rbac.authorization.k8s.io/v1
+kind: ClusterRoleBinding
+metadata:
+  name: tailscale-operator
+subjects:
+- kind: ServiceAccount
+  name: operator
+  namespace: {{ .Release.Namespace }}
+roleRef:
+  kind: ClusterRole
+  name: tailscale-operator
+  apiGroup: rbac.authorization.k8s.io
+---
+apiVersion: rbac.authorization.k8s.io/v1
+kind: Role
+metadata:
+  name: operator
+  namespace: {{ .Release.Namespace }}
+rules:
+- apiGroups: [""]
+  resources: ["secrets"]
+  verbs: ["*"]
+- apiGroups: ["apps"]
+  resources: ["statefulsets"]
+  verbs: ["*"]
+---
+apiVersion: rbac.authorization.k8s.io/v1
+kind: RoleBinding
+metadata:
+  name: operator
+  namespace: {{ .Release.Namespace }}
+subjects:
+- kind: ServiceAccount
+  name: operator
+  namespace: {{ .Release.Namespace }}
+roleRef:
+  kind: Role
+  name: operator
+  apiGroup: rbac.authorization.k8s.io

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

@@ -0,0 +1,32 @@
+# Copyright (c) Tailscale Inc & AUTHORS
+# SPDX-License-Identifier: BSD-3-Clause
+
+apiVersion: v1
+kind: ServiceAccount
+metadata:
+  name: proxies
+  namespace: {{ .Release.Namespace }}
+---
+apiVersion: rbac.authorization.k8s.io/v1
+kind: Role
+metadata:
+  name: proxies
+  namespace: {{ .Release.Namespace }}
+rules:
+- apiGroups: [""]
+  resources: ["secrets"]
+  verbs: ["*"]
+---
+apiVersion: rbac.authorization.k8s.io/v1
+kind: RoleBinding
+metadata:
+  name: proxies
+  namespace: {{ .Release.Namespace }}
+subjects:
+- kind: ServiceAccount
+  name: proxies
+  namespace: {{ .Release.Namespace }}
+roleRef:
+  kind: Role
+  name: proxies
+  apiGroup: rbac.authorization.k8s.io

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

@@ -0,0 +1,45 @@
+# Copyright (c) Tailscale Inc & AUTHORS
+# SPDX-License-Identifier: BSD-3-Clause
+
+# Operator oauth credentials. If set a Kubernetes Secret with the provided
+# values will be created in the operator namespace. If unset a Secret named
+# operator-oauth must be precreated.
+# oauth:
+#   clientId: ""
+#   clientSecret: ""
+
+operatorConfig:
+  image:
+    repo: tailscale/k8s-operator
+    # Digest will be prioritized over tag. If neither are set appVersion will be
+    # used.
+    tag: ""
+    digest: ""
+  logging: "info"
+  hostname: "tailscale-operator"
+  nodeSelector:
+    kubernetes.io/os: linux
+
+
+# proxyConfig contains configuraton that will be applied to any ingress/egress
+# proxies created by the operator.
+# https://tailscale.com/kb/1236/kubernetes-operator/#cluster-ingress
+# https://tailscale.com/kb/1236/kubernetes-operator/#cluster-egress
+proxyConfig:
+  image:
+    repo: tailscale/tailscale
+    # Digest will be prioritized over tag. If neither are set appVersion will be
+    # used.
+    tag: ""
+    digest: ""
+  # ACL tag that operator will tag proxies with. Operator must be made owner of
+  # these tags
+  # https://tailscale.com/kb/1236/kubernetes-operator/?q=operator#setting-up-the-kubernetes-operator
+  defaultTags: tag:k8s
+  firewallMode: auto
+
+# apiServerProxyConfig allows to configure whether the operator should expose
+# Kubernetes API server.
+# https://tailscale.com/kb/1236/kubernetes-operator/#accessing-the-kubernetes-control-plane-using-an-api-server-proxy
+apiServerProxyConfig:
+  mode: "false" # "true", "false", "noauth"

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

@@ -151,8 +151,10 @@ spec:
               value: tailscale/tailscale:unstable
             - name: PROXY_TAGS
               value: tag:k8s
-            - name: AUTH_PROXY
+            - name: APISERVER_PROXY
               value: "false"
+            - name: PROXY_FIREWALL_MODE
+              value: auto
           volumeMounts:
           - name: oauth
             mountPath: /oauth

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

@@ -12,7 +12,6 @@ spec:
       serviceAccountName: proxies
       initContainers:
         - name: sysctler
-          image: busybox
           securityContext:
             privileged: true
           command: ["/bin/sh"]

cmd/k8s-operator/ingress.go

@@ -192,8 +192,15 @@ func (a *IngressReconciler) maybeProvision(ctx context.Context, logger *zap.Suga
 		}
 	}
 	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 {
-		if rule.Host != "" {
+		// 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
 		}
@@ -208,8 +215,8 @@ func (a *IngressReconciler) maybeProvision(ctx context.Context, logger *zap.Suga
 		tags = strings.Split(tstr, ",")
 	}
 	hostname := ing.Namespace + "-" + ing.Name + "-ingress"
-	if ing.Spec.TLS != nil && len(ing.Spec.TLS) > 0 && len(ing.Spec.TLS[0].Hosts) > 0 {
-		hostname, _, _ = strings.Cut(ing.Spec.TLS[0].Hosts[0], ".")
+	if tlsHost != "" {
+		hostname, _, _ = strings.Cut(tlsHost, ".")
 	}
 
 	sts := &tailscaleSTSConfig{

cmd/k8s-operator/operator.go

@@ -52,6 +52,7 @@ func main() {
 		image             = defaultEnv("PROXY_IMAGE", "tailscale/tailscale:latest")
 		priorityClassName = defaultEnv("PROXY_PRIORITY_CLASS_NAME", "")
 		tags              = defaultEnv("PROXY_TAGS", "tag:k8s")
+		tsFirewallMode    = defaultEnv("PROXY_FIREWALL_MODE", "")
 	)
 
 	var opts []kzap.Opts
@@ -66,18 +67,27 @@ func main() {
 	zlog := kzap.NewRaw(opts...).Sugar()
 	logf.SetLogger(zapr.NewLogger(zlog.Desugar()))
 
+	// 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.
+	mode := parseAPIProxyMode()
+	if mode == apiserverProxyModeDisabled {
+		hostinfo.SetApp("k8s-operator")
+	} else {
+		hostinfo.SetApp("k8s-operator-proxy")
+	}
+
 	s, tsClient := initTSNet(zlog)
 	defer s.Close()
 	restConfig := config.GetConfigOrDie()
-	maybeLaunchAPIServerProxy(zlog, restConfig, s)
-	runReconcilers(zlog, s, tsNamespace, restConfig, tsClient, image, priorityClassName, tags)
+	maybeLaunchAPIServerProxy(zlog, restConfig, s, mode)
+	runReconcilers(zlog, s, tsNamespace, restConfig, tsClient, image, priorityClassName, tags, tsFirewallMode)
 }
 
 // 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) {
-	hostinfo.SetApp("k8s-operator")
 	var (
 		clientIDPath     = defaultEnv("CLIENT_ID_FILE", "")
 		clientSecretPath = defaultEnv("CLIENT_SECRET_FILE", "")
@@ -179,7 +189,7 @@ waitOnline:
 
 // runReconcilers starts the controller-runtime manager and registers the
 // ServiceReconciler. It blocks forever.
-func runReconcilers(zlog *zap.SugaredLogger, s *tsnet.Server, tsNamespace string, restConfig *rest.Config, tsClient *tailscale.Client, image, priorityClassName, tags string) {
+func runReconcilers(zlog *zap.SugaredLogger, s *tsnet.Server, tsNamespace string, restConfig *rest.Config, tsClient *tailscale.Client, image, priorityClassName, tags, tsFirewallMode string) {
 	var (
 		isDefaultLoadBalancer = defaultBool("OPERATOR_DEFAULT_LOAD_BALANCER", false)
 	)
@@ -216,6 +226,7 @@ func runReconcilers(zlog *zap.SugaredLogger, s *tsnet.Server, tsNamespace string
 		operatorNamespace:      tsNamespace,
 		proxyImage:             image,
 		proxyPriorityClassName: priorityClassName,
+		tsFirewallMode:         tsFirewallMode,
 	}
 	err = builder.
 		ControllerManagedBy(mgr).
@@ -228,6 +239,7 @@ func runReconcilers(zlog *zap.SugaredLogger, s *tsnet.Server, tsNamespace string
 			Client:                mgr.GetClient(),
 			logger:                zlog.Named("service-reconciler"),
 			isDefaultLoadBalancer: isDefaultLoadBalancer,
+			recorder:              eventRecorder,
 		})
 	if err != nil {
 		startlog.Fatalf("could not create controller: %v", err)

cmd/k8s-operator/operator_test.go

@@ -70,7 +70,12 @@ func TestLoadBalancerClass(t *testing.T) {
 
 	expectEqual(t, fc, expectedSecret(fullName))
 	expectEqual(t, fc, expectedHeadlessService(shortName))
-	expectEqual(t, fc, expectedSTS(shortName, fullName, "default-test", ""))
+	o := stsOpts{
+		name:       shortName,
+		secretName: fullName,
+		hostname:   "default-test",
+	}
+	expectEqual(t, fc, expectedSTS(o))
 
 	// Normally the Tailscale proxy pod would come up here and write its info
 	// into the secret. Simulate that, then verify reconcile again and verify
@@ -202,7 +207,13 @@ func TestTailnetTargetIPAnnotation(t *testing.T) {
 
 	expectEqual(t, fc, expectedSecret(fullName))
 	expectEqual(t, fc, expectedHeadlessService(shortName))
-	expectEqual(t, fc, expectedEgressSTS(shortName, fullName, tailnetTargetIP, "default-test", ""))
+	o := stsOpts{
+		name:            shortName,
+		secretName:      fullName,
+		tailnetTargetIP: tailnetTargetIP,
+		hostname:        "default-test",
+	}
+	expectEqual(t, fc, expectedSTS(o))
 	want := &corev1.Service{
 		TypeMeta: metav1.TypeMeta{
 			Kind:       "Service",
@@ -226,7 +237,13 @@ func TestTailnetTargetIPAnnotation(t *testing.T) {
 	expectEqual(t, fc, want)
 	expectEqual(t, fc, expectedSecret(fullName))
 	expectEqual(t, fc, expectedHeadlessService(shortName))
-	expectEqual(t, fc, expectedEgressSTS(shortName, fullName, tailnetTargetIP, "default-test", ""))
+	o = stsOpts{
+		name:            shortName,
+		secretName:      fullName,
+		tailnetTargetIP: tailnetTargetIP,
+		hostname:        "default-test",
+	}
+	expectEqual(t, fc, expectedSTS(o))
 
 	// Change the tailscale-target-ip annotation which should update the
 	// StatefulSet
@@ -305,7 +322,12 @@ func TestAnnotations(t *testing.T) {
 
 	expectEqual(t, fc, expectedSecret(fullName))
 	expectEqual(t, fc, expectedHeadlessService(shortName))
-	expectEqual(t, fc, expectedSTS(shortName, fullName, "default-test", ""))
+	o := stsOpts{
+		name:       shortName,
+		secretName: fullName,
+		hostname:   "default-test",
+	}
+	expectEqual(t, fc, expectedSTS(o))
 	want := &corev1.Service{
 		TypeMeta: metav1.TypeMeta{
 			Kind:       "Service",
@@ -405,7 +427,12 @@ func TestAnnotationIntoLB(t *testing.T) {
 
 	expectEqual(t, fc, expectedSecret(fullName))
 	expectEqual(t, fc, expectedHeadlessService(shortName))
-	expectEqual(t, fc, expectedSTS(shortName, fullName, "default-test", ""))
+	o := stsOpts{
+		name:       shortName,
+		secretName: fullName,
+		hostname:   "default-test",
+	}
+	expectEqual(t, fc, expectedSTS(o))
 
 	// 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
@@ -450,7 +477,12 @@ func TestAnnotationIntoLB(t *testing.T) {
 	expectReconciled(t, sr, "default", "test")
 	// None of the proxy machinery should have changed...
 	expectEqual(t, fc, expectedHeadlessService(shortName))
-	expectEqual(t, fc, expectedSTS(shortName, fullName, "default-test", ""))
+	o = stsOpts{
+		name:       shortName,
+		secretName: fullName,
+		hostname:   "default-test",
+	}
+	expectEqual(t, fc, expectedSTS(o))
 	// ... but the service should have a LoadBalancer status.
 
 	want = &corev1.Service{
@@ -528,7 +560,12 @@ func TestLBIntoAnnotation(t *testing.T) {
 
 	expectEqual(t, fc, expectedSecret(fullName))
 	expectEqual(t, fc, expectedHeadlessService(shortName))
-	expectEqual(t, fc, expectedSTS(shortName, fullName, "default-test", ""))
+	o := stsOpts{
+		name:       shortName,
+		secretName: fullName,
+		hostname:   "default-test",
+	}
+	expectEqual(t, fc, expectedSTS(o))
 
 	// Normally the Tailscale proxy pod would come up here and write its info
 	// into the secret. Simulate that, then verify reconcile again and verify
@@ -591,7 +628,12 @@ func TestLBIntoAnnotation(t *testing.T) {
 	expectReconciled(t, sr, "default", "test")
 
 	expectEqual(t, fc, expectedHeadlessService(shortName))
-	expectEqual(t, fc, expectedSTS(shortName, fullName, "default-test", ""))
+	o = stsOpts{
+		name:       shortName,
+		secretName: fullName,
+		hostname:   "default-test",
+	}
+	expectEqual(t, fc, expectedSTS(o))
 
 	want = &corev1.Service{
 		TypeMeta: metav1.TypeMeta{
@@ -661,7 +703,12 @@ func TestCustomHostname(t *testing.T) {
 
 	expectEqual(t, fc, expectedSecret(fullName))
 	expectEqual(t, fc, expectedHeadlessService(shortName))
-	expectEqual(t, fc, expectedSTS(shortName, fullName, "reindeer-flotilla", ""))
+	o := stsOpts{
+		name:       shortName,
+		secretName: fullName,
+		hostname:   "reindeer-flotilla",
+	}
+	expectEqual(t, fc, expectedSTS(o))
 	want := &corev1.Service{
 		TypeMeta: metav1.TypeMeta{
 			Kind:       "Service",
@@ -735,7 +782,7 @@ func TestCustomPriorityClassName(t *testing.T) {
 			defaultTags:            []string{"tag:k8s"},
 			operatorNamespace:      "operator-ns",
 			proxyImage:             "tailscale/tailscale",
-			proxyPriorityClassName: "tailscale-critical",
+			proxyPriorityClassName: "custom-priority-class-name",
 		},
 		logger: zl.Sugar(),
 	}
@@ -752,7 +799,7 @@ func TestCustomPriorityClassName(t *testing.T) {
 			UID: types.UID("1234-UID"),
 			Annotations: map[string]string{
 				"tailscale.com/expose":   "true",
-				"tailscale.com/hostname": "custom-priority-class-name",
+				"tailscale.com/hostname": "tailscale-critical",
 			},
 		},
 		Spec: corev1.ServiceSpec{
@@ -764,8 +811,14 @@ func TestCustomPriorityClassName(t *testing.T) {
 	expectReconciled(t, sr, "default", "test")
 
 	fullName, shortName := findGenName(t, fc, "default", "test")
+	o := stsOpts{
+		name:              shortName,
+		secretName:        fullName,
+		hostname:          "tailscale-critical",
+		priorityClassName: "custom-priority-class-name",
+	}
 
-	expectEqual(t, fc, expectedSTS(shortName, fullName, "custom-priority-class-name", "tailscale-critical"))
+	expectEqual(t, fc, expectedSTS(o))
 }
 
 func TestDefaultLoadBalancer(t *testing.T) {
@@ -811,7 +864,63 @@ func TestDefaultLoadBalancer(t *testing.T) {
 
 	expectEqual(t, fc, expectedSecret(fullName))
 	expectEqual(t, fc, expectedHeadlessService(shortName))
-	expectEqual(t, fc, expectedSTS(shortName, fullName, "default-test", ""))
+	o := stsOpts{
+		name:       shortName,
+		secretName: fullName,
+		hostname:   "default-test",
+	}
+	expectEqual(t, fc, expectedSTS(o))
+}
+
+func TestProxyFirewallMode(t *testing.T) {
+	fc := fake.NewFakeClient()
+	ft := &fakeTSClient{}
+	zl, err := zap.NewDevelopment()
+	if err != nil {
+		t.Fatal(err)
+	}
+	sr := &ServiceReconciler{
+		Client: fc,
+		ssr: &tailscaleSTSReconciler{
+			Client:            fc,
+			tsClient:          ft,
+			defaultTags:       []string{"tag:k8s"},
+			operatorNamespace: "operator-ns",
+			proxyImage:        "tailscale/tailscale",
+			tsFirewallMode:    "nftables",
+		},
+		logger:                zl.Sugar(),
+		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")
+	o := stsOpts{
+		name:         shortName,
+		secretName:   fullName,
+		hostname:     "default-test",
+		firewallMode: "nftables",
+	}
+	expectEqual(t, fc, expectedSTS(o))
+
 }
 
 func expectedSecret(name string) *corev1.Secret {
@@ -862,83 +971,44 @@ func expectedHeadlessService(name string) *corev1.Service {
 	}
 }
 
-func expectedSTS(stsName, secretName, hostname, priorityClassName string) *appsv1.StatefulSet {
-	return &appsv1.StatefulSet{
-		TypeMeta: metav1.TypeMeta{
-			Kind:       "StatefulSet",
-			APIVersion: "apps/v1",
-		},
-		ObjectMeta: metav1.ObjectMeta{
-			Name:      stsName,
-			Namespace: "operator-ns",
-			Labels: map[string]string{
-				"tailscale.com/managed":              "true",
-				"tailscale.com/parent-resource":      "test",
-				"tailscale.com/parent-resource-ns":   "default",
-				"tailscale.com/parent-resource-type": "svc",
-			},
-		},
-		Spec: appsv1.StatefulSetSpec{
-			Replicas: ptr.To[int32](1),
-			Selector: &metav1.LabelSelector{
-				MatchLabels: map[string]string{"app": "1234-UID"},
-			},
-			ServiceName: stsName,
-			Template: corev1.PodTemplateSpec{
-				ObjectMeta: metav1.ObjectMeta{
-					Annotations: map[string]string{
-						"tailscale.com/operator-last-set-hostname":   hostname,
-						"tailscale.com/operator-last-set-cluster-ip": "10.20.30.40",
-					},
-					DeletionGracePeriodSeconds: ptr.To[int64](10),
-					Labels:                     map[string]string{"app": "1234-UID"},
-				},
-				Spec: corev1.PodSpec{
-					ServiceAccountName: "proxies",
-					PriorityClassName:  priorityClassName,
-					InitContainers: []corev1.Container{
-						{
-							Name:    "sysctler",
-							Image:   "busybox",
-							Command: []string{"/bin/sh"},
-							Args:    []string{"-c", "sysctl -w net.ipv4.ip_forward=1 net.ipv6.conf.all.forwarding=1"},
-							SecurityContext: &corev1.SecurityContext{
-								Privileged: ptr.To(true),
-							},
-						},
-					},
-					Containers: []corev1.Container{
-						{
-							Name:  "tailscale",
-							Image: "tailscale/tailscale",
-							Env: []corev1.EnvVar{
-								{Name: "TS_USERSPACE", Value: "false"},
-								{Name: "TS_AUTH_ONCE", Value: "true"},
-								{Name: "TS_KUBE_SECRET", Value: secretName},
-								{Name: "TS_HOSTNAME", Value: hostname},
-								{Name: "TS_DEST_IP", Value: "10.20.30.40"},
-							},
-							SecurityContext: &corev1.SecurityContext{
-								Capabilities: &corev1.Capabilities{
-									Add: []corev1.Capability{"NET_ADMIN"},
-								},
-							},
-							ImagePullPolicy: "Always",
-						},
-					},
-				},
-			},
-		},
+func expectedSTS(opts stsOpts) *appsv1.StatefulSet {
+	containerEnv := []corev1.EnvVar{
+		{Name: "TS_USERSPACE", Value: "false"},
+		{Name: "TS_AUTH_ONCE", Value: "true"},
+		{Name: "TS_KUBE_SECRET", Value: opts.secretName},
+		{Name: "TS_HOSTNAME", Value: opts.hostname},
+	}
+	annots := map[string]string{
+		"tailscale.com/operator-last-set-hostname": opts.hostname,
+	}
+	if opts.tailnetTargetIP != "" {
+		annots["tailscale.com/operator-last-set-ts-tailnet-target-ip"] = opts.tailnetTargetIP
+		containerEnv = append(containerEnv, corev1.EnvVar{
+			Name:  "TS_TAILNET_TARGET_IP",
+			Value: opts.tailnetTargetIP,
+		})
+	} else {
+		containerEnv = append(containerEnv, corev1.EnvVar{
+			Name:  "TS_DEST_IP",
+			Value: "10.20.30.40",
+		})
+
+		annots["tailscale.com/operator-last-set-cluster-ip"] = "10.20.30.40"
+
+	}
+	if opts.firewallMode != "" {
+		containerEnv = append(containerEnv, corev1.EnvVar{
+			Name:  "TS_DEBUG_FIREWALL_MODE",
+			Value: opts.firewallMode,
+		})
 	}
-}
-func expectedEgressSTS(stsName, secretName, tailnetTargetIP, hostname, priorityClassName string) *appsv1.StatefulSet {
 	return &appsv1.StatefulSet{
 		TypeMeta: metav1.TypeMeta{
 			Kind:       "StatefulSet",
 			APIVersion: "apps/v1",
 		},
 		ObjectMeta: metav1.ObjectMeta{
-			Name:      stsName,
+			Name:      opts.name,
 			Namespace: "operator-ns",
 			Labels: map[string]string{
 				"tailscale.com/managed":              "true",
@@ -952,23 +1022,20 @@ func expectedEgressSTS(stsName, secretName, tailnetTargetIP, hostname, priorityC
 			Selector: &metav1.LabelSelector{
 				MatchLabels: map[string]string{"app": "1234-UID"},
 			},
-			ServiceName: stsName,
+			ServiceName: opts.name,
 			Template: corev1.PodTemplateSpec{
 				ObjectMeta: metav1.ObjectMeta{
-					Annotations: map[string]string{
-						"tailscale.com/operator-last-set-hostname":             hostname,
-						"tailscale.com/operator-last-set-ts-tailnet-target-ip": tailnetTargetIP,
-					},
+					Annotations:                annots,
 					DeletionGracePeriodSeconds: ptr.To[int64](10),
 					Labels:                     map[string]string{"app": "1234-UID"},
 				},
 				Spec: corev1.PodSpec{
 					ServiceAccountName: "proxies",
-					PriorityClassName:  priorityClassName,
+					PriorityClassName:  opts.priorityClassName,
 					InitContainers: []corev1.Container{
 						{
 							Name:    "sysctler",
-							Image:   "busybox",
+							Image:   "tailscale/tailscale",
 							Command: []string{"/bin/sh"},
 							Args:    []string{"-c", "sysctl -w net.ipv4.ip_forward=1 net.ipv6.conf.all.forwarding=1"},
 							SecurityContext: &corev1.SecurityContext{
@@ -980,13 +1047,7 @@ func expectedEgressSTS(stsName, secretName, tailnetTargetIP, hostname, priorityC
 						{
 							Name:  "tailscale",
 							Image: "tailscale/tailscale",
-							Env: []corev1.EnvVar{
-								{Name: "TS_USERSPACE", Value: "false"},
-								{Name: "TS_AUTH_ONCE", Value: "true"},
-								{Name: "TS_KUBE_SECRET", Value: secretName},
-								{Name: "TS_HOSTNAME", Value: hostname},
-								{Name: "TS_TAILNET_TARGET_IP", Value: tailnetTargetIP},
-							},
+							Env:   containerEnv,
 							SecurityContext: &corev1.SecurityContext{
 								Capabilities: &corev1.Capabilities{
 									Add: []corev1.Capability{"NET_ADMIN"},
@@ -1126,6 +1187,15 @@ func expectRequeue(t *testing.T, sr *ServiceReconciler, ns, name string) {
 	}
 }
 
+type stsOpts struct {
+	name              string
+	secretName        string
+	hostname          string
+	priorityClassName string
+	firewallMode      string
+	tailnetTargetIP   string
+}
+
 type fakeTSClient struct {
 	sync.Mutex
 	keyRequests []tailscale.KeyCapabilities

cmd/k8s-operator/proxy.go

@@ -21,7 +21,6 @@ import (
 	"k8s.io/client-go/transport"
 	"tailscale.com/client/tailscale"
 	"tailscale.com/client/tailscale/apitype"
-	"tailscale.com/hostinfo"
 	"tailscale.com/tailcfg"
 	"tailscale.com/tsnet"
 	"tailscale.com/types/logger"
@@ -84,13 +83,14 @@ func parseAPIProxyMode() apiServerProxyMode {
 // maybeLaunchAPIServerProxy launches the auth proxy, which is a small HTTP server
 // that authenticates requests using the Tailscale LocalAPI and then proxies
 // them to the kube-apiserver.
-func maybeLaunchAPIServerProxy(zlog *zap.SugaredLogger, restConfig *rest.Config, s *tsnet.Server) {
-	mode := parseAPIProxyMode()
+func maybeLaunchAPIServerProxy(zlog *zap.SugaredLogger, restConfig *rest.Config, s *tsnet.Server, mode apiServerProxyMode) {
 	if mode == apiserverProxyModeDisabled {
 		return
 	}
-	hostinfo.SetApp("k8s-operator-proxy")
 	startlog := zlog.Named("launchAPIProxy")
+	if mode == apiserverProxyModeNoAuth {
+		restConfig = rest.AnonymousClientConfig(restConfig)
+	}
 	cfg, err := restConfig.TransportConfig()
 	if err != nil {
 		startlog.Fatalf("could not get rest.TransportConfig(): %v", err)
@@ -166,10 +166,11 @@ func runAPIServerProxy(s *tsnet.Server, rt http.RoundTripper, logf logger.Logf,
 		logf: logf,
 		lc:   lc,
 		rp: &httputil.ReverseProxy{
-			Director: func(r *http.Request) {
+			Rewrite: func(r *httputil.ProxyRequest) {
 				// Replace the URL with the Kubernetes APIServer.
-				r.URL.Scheme = u.Scheme
-				r.URL.Host = u.Host
+
+				r.Out.URL.Scheme = u.Scheme
+				r.Out.URL.Host = u.Host
 				if mode == apiserverProxyModeNoAuth {
 					// If we are not providing authentication, then we are just
 					// proxying to the Kubernetes API, so we don't need to do
@@ -184,18 +185,18 @@ func runAPIServerProxy(s *tsnet.Server, rt http.RoundTripper, logf logger.Logf,
 
 				// Out of paranoia, remove all authentication headers that might
 				// have been set by the client.
-				r.Header.Del("Authorization")
-				r.Header.Del("Impersonate-Group")
-				r.Header.Del("Impersonate-User")
-				r.Header.Del("Impersonate-Uid")
-				for k := range r.Header {
+				r.Out.Header.Del("Authorization")
+				r.Out.Header.Del("Impersonate-Group")
+				r.Out.Header.Del("Impersonate-User")
+				r.Out.Header.Del("Impersonate-Uid")
+				for k := range r.Out.Header {
 					if strings.HasPrefix(k, "Impersonate-Extra-") {
-						r.Header.Del(k)
+						r.Out.Header.Del(k)
 					}
 				}
 
 				// Now add the impersonation headers that we want.
-				if err := addImpersonationHeaders(r); err != nil {
+				if err := addImpersonationHeaders(r.Out); err != nil {
 					panic("failed to add impersonation headers: " + err.Error())
 				}
 			},

cmd/k8s-operator/sts.go

@@ -9,7 +9,9 @@ import (
 	"context"
 	_ "embed"
 	"encoding/json"
+	"errors"
 	"fmt"
+	"net/http"
 	"os"
 	"strings"
 
@@ -79,6 +81,14 @@ type tailscaleSTSReconciler struct {
 	operatorNamespace      string
 	proxyImage             string
 	proxyPriorityClassName string
+	tsFirewallMode         string
+}
+
+func (sts tailscaleSTSReconciler) validate() error {
+	if sts.tsFirewallMode != "" && !isValidFirewallMode(sts.tsFirewallMode) {
+		return fmt.Errorf("invalid proxy firewall mode %s, valid modes are iptables, nftables or unset", sts.tsFirewallMode)
+	}
+	return nil
 }
 
 // IsHTTPSEnabledOnTailnet reports whether HTTPS is enabled on the tailnet.
@@ -141,10 +151,16 @@ func (a *tailscaleSTSReconciler) Cleanup(ctx context.Context, logger *zap.Sugare
 		return false, fmt.Errorf("getting device info: %w", err)
 	}
 	if id != "" {
-		// TODO: handle case where the device is already deleted, but the secret
-		// is still around.
+		logger.Debugf("deleting device %s from control", string(id))
 		if err := a.tsClient.DeleteDevice(ctx, string(id)); err != nil {
-			return false, fmt.Errorf("deleting device: %w", err)
+			errResp := &tailscale.ErrResponse{}
+			if ok := errors.As(err, errResp); ok && errResp.Status == http.StatusNotFound {
+				logger.Debugf("device %s not found, likely because it has already been deleted from control", string(id))
+			} else {
+				return false, fmt.Errorf("deleting device: %w", err)
+			}
+		} else {
+			logger.Debugf("device %s deleted from control", string(id))
 		}
 	}
 
@@ -291,10 +307,10 @@ func (a *tailscaleSTSReconciler) newAuthKey(ctx context.Context, tags []string)
 	return key, nil
 }
 
-//go:embed manifests/proxy.yaml
+//go:embed deploy/manifests/proxy.yaml
 var proxyYaml []byte
 
-//go:embed manifests/userspace-proxy.yaml
+//go:embed deploy/manifests/userspace-proxy.yaml
 var userspaceProxyYaml []byte
 
 func (a *tailscaleSTSReconciler) reconcileSTS(ctx context.Context, logger *zap.SugaredLogger, sts *tailscaleSTSConfig, headlessSvc *corev1.Service, authKeySecret string) (*appsv1.StatefulSet, error) {
@@ -307,6 +323,13 @@ func (a *tailscaleSTSReconciler) reconcileSTS(ctx context.Context, logger *zap.S
 		if err := yaml.Unmarshal(proxyYaml, &ss); err != nil {
 			return nil, fmt.Errorf("failed to unmarshal proxy spec: %w", err)
 		}
+		for i := range ss.Spec.Template.Spec.InitContainers {
+			c := &ss.Spec.Template.Spec.InitContainers[i]
+			if c.Name == "sysctler" {
+				c.Image = a.proxyImage
+				break
+			}
+		}
 	}
 	container := &ss.Spec.Template.Spec.Containers[0]
 	container.Image = a.proxyImage
@@ -353,6 +376,13 @@ func (a *tailscaleSTSReconciler) reconcileSTS(ctx context.Context, logger *zap.S
 			},
 		})
 	}
+	if a.tsFirewallMode != "" {
+		container.Env = append(container.Env, corev1.EnvVar{
+			Name:  "TS_DEBUG_FIREWALL_MODE",
+			Value: a.tsFirewallMode,
+		},
+		)
+	}
 	ss.ObjectMeta = metav1.ObjectMeta{
 		Name:      headlessSvc.Name,
 		Namespace: a.operatorNamespace,
@@ -492,3 +522,7 @@ func nameForService(svc *corev1.Service) (string, error) {
 	}
 	return svc.Namespace + "-" + svc.Name, nil
 }
+
+func isValidFirewallMode(m string) bool {
+	return m == "auto" || m == "nftables" || m == "iptables"
+}

cmd/k8s-operator/svc.go

@@ -17,6 +17,7 @@ import (
 	corev1 "k8s.io/api/core/v1"
 	apierrors "k8s.io/apimachinery/pkg/api/errors"
 	"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/util/clientmetric"
@@ -37,6 +38,8 @@ type ServiceReconciler struct {
 	// managedEgressProxies is a set of all egress proxies that we're currently
 	// managing. This is only used for metrics.
 	managedEgressProxies set.Slice[types.UID]
+
+	recorder record.EventRecorder
 }
 
 var (
@@ -136,6 +139,15 @@ func (a *ServiceReconciler) maybeCleanup(ctx context.Context, logger *zap.Sugare
 // This function adds a finalizer to svc, ensuring that we can handle orderly
 // deprovisioning later.
 func (a *ServiceReconciler) maybeProvision(ctx context.Context, logger *zap.SugaredLogger, svc *corev1.Service) error {
+	// run for proxy config related validations here as opposed to running
+	// them earlier. This is to prevent cleanup etc being blocked on a
+	// misconfigured proxy param
+	if err := a.ssr.validate(); err != nil {
+		msg := fmt.Sprintf("unable to provision proxy resources: invalid config: %v", err)
+		a.recorder.Event(svc, corev1.EventTypeWarning, "INVALIDCONFIG", msg)
+		a.logger.Error(msg)
+		return nil
+	}
 	hostname, err := nameForService(svc)
 	if err != nil {
 		return err

cmd/sniproxy/handlers.go

@@ -0,0 +1,104 @@
+// Copyright (c) Tailscale Inc & AUTHORS
+// SPDX-License-Identifier: BSD-3-Clause
+
+package main
+
+import (
+	"context"
+	"fmt"
+	"log"
+	"math/rand"
+	"net"
+	"net/netip"
+	"slices"
+
+	"inet.af/tcpproxy"
+	"tailscale.com/net/netutil"
+)
+
+type tcpRoundRobinHandler struct {
+	// To is a list of destination addresses to forward to.
+	// An entry may be either an IP address or a DNS name.
+	To []string
+
+	// DialContext is used to make the outgoing TCP connection.
+	DialContext func(ctx context.Context, network, address string) (net.Conn, error)
+
+	// ReachableIPs enumerates the IP addresses this handler is reachable on.
+	ReachableIPs []netip.Addr
+}
+
+// ReachableOn returns the IP addresses this handler is reachable on.
+func (h *tcpRoundRobinHandler) ReachableOn() []netip.Addr {
+	return h.ReachableIPs
+}
+
+func (h *tcpRoundRobinHandler) Handle(c net.Conn) {
+	addrPortStr := c.LocalAddr().String()
+	_, port, err := net.SplitHostPort(addrPortStr)
+	if err != nil {
+		log.Printf("tcpRoundRobinHandler.Handle: bogus addrPort %q", addrPortStr)
+		c.Close()
+		return
+	}
+
+	var p tcpproxy.Proxy
+	p.ListenFunc = func(net, laddr string) (net.Listener, error) {
+		return netutil.NewOneConnListener(c, nil), nil
+	}
+
+	dest := h.To[rand.Intn(len(h.To))]
+	dial := &tcpproxy.DialProxy{
+		Addr:        fmt.Sprintf("%s:%s", dest, port),
+		DialContext: h.DialContext,
+	}
+
+	p.AddRoute(addrPortStr, dial)
+	p.Start()
+}
+
+type tcpSNIHandler struct {
+	// Allowlist enumerates the FQDNs which may be proxied via SNI. An
+	// empty slice means all domains are permitted.
+	Allowlist []string
+
+	// DialContext is used to make the outgoing TCP connection.
+	DialContext func(ctx context.Context, network, address string) (net.Conn, error)
+
+	// ReachableIPs enumerates the IP addresses this handler is reachable on.
+	ReachableIPs []netip.Addr
+}
+
+// ReachableOn returns the IP addresses this handler is reachable on.
+func (h *tcpSNIHandler) ReachableOn() []netip.Addr {
+	return h.ReachableIPs
+}
+
+func (h *tcpSNIHandler) Handle(c net.Conn) {
+	addrPortStr := c.LocalAddr().String()
+	_, port, err := net.SplitHostPort(addrPortStr)
+	if err != nil {
+		log.Printf("tcpSNIHandler.Handle: bogus addrPort %q", addrPortStr)
+		c.Close()
+		return
+	}
+
+	var p tcpproxy.Proxy
+	p.ListenFunc = func(net, laddr string) (net.Listener, error) {
+		return netutil.NewOneConnListener(c, nil), nil
+	}
+	p.AddSNIRouteFunc(addrPortStr, func(ctx context.Context, sniName string) (t tcpproxy.Target, ok bool) {
+		if len(h.Allowlist) > 0 {
+			// TODO(tom): handle subdomains
+			if slices.Index(h.Allowlist, sniName) < 0 {
+				return nil, false
+			}
+		}
+
+		return &tcpproxy.DialProxy{
+			Addr:        net.JoinHostPort(sniName, port),
+			DialContext: h.DialContext,
+		}, true
+	})
+	p.Start()
+}

cmd/sniproxy/handlers_test.go

@@ -0,0 +1,159 @@
+// Copyright (c) Tailscale Inc & AUTHORS
+// SPDX-License-Identifier: BSD-3-Clause
+
+package main
+
+import (
+	"bytes"
+	"context"
+	"encoding/hex"
+	"io"
+	"net"
+	"net/netip"
+	"strings"
+	"testing"
+
+	"tailscale.com/net/memnet"
+)
+
+func echoConnOnce(conn net.Conn) {
+	defer conn.Close()
+
+	b := make([]byte, 256)
+	n, err := conn.Read(b)
+	if err != nil {
+		return
+	}
+
+	if _, err := conn.Write(b[:n]); err != nil {
+		return
+	}
+}
+
+func TestTCPRoundRobinHandler(t *testing.T) {
+	h := tcpRoundRobinHandler{
+		To: []string{"yeet.com"},
+		DialContext: func(ctx context.Context, network, addr string) (net.Conn, error) {
+			if network != "tcp" {
+				t.Errorf("network = %s, want %s", network, "tcp")
+			}
+			if addr != "yeet.com:22" {
+				t.Errorf("addr = %s, want %s", addr, "yeet.com:22")
+			}
+
+			c, s := memnet.NewConn("outbound", 1024)
+			go echoConnOnce(s)
+			return c, nil
+		},
+	}
+
+	cSock, sSock := memnet.NewTCPConn(netip.MustParseAddrPort("10.64.1.2:22"), netip.MustParseAddrPort("10.64.1.2:22"), 1024)
+	h.Handle(sSock)
+
+	// Test data write and read, the other end will echo back
+	// a single stanza
+	want := "hello"
+	if _, err := io.WriteString(cSock, want); err != nil {
+		t.Fatal(err)
+	}
+	got := make([]byte, len(want))
+	if _, err := io.ReadAtLeast(cSock, got, len(got)); err != nil {
+		t.Fatal(err)
+	}
+	if string(got) != want {
+		t.Errorf("got %q, want %q", got, want)
+	}
+
+	// The other end closed the socket after the first echo, so
+	// any following read should error.
+	io.WriteString(cSock, "deadass heres some data on god fr")
+	if _, err := io.ReadAtLeast(cSock, got, len(got)); err == nil {
+		t.Error("read succeeded on closed socket")
+	}
+}
+
+// Capture of first TCP data segment for a connection to https://pkgs.tailscale.com
+const tlsStart = `45000239ff1840004006f9f5c0a801f2
+c726b5efcf9e01bbe803b21394e3b752
+801801f641dc00000101080ade3474f2
+2fb93ee71603010200010001fc030303
+c3acbd19d2624765bb19af4bce03365e
+1d197f5bb939cdadeff26b0f8e7a0620
+295b04127b82bae46aac4ff58cffef25
+eba75a4b7a6de729532c411bd9dd0d2c
+00203a3a130113021303c02bc02fc02c
+c030cca9cca8c013c014009c009d002f
+003501000193caca0000000a000a0008
+1a1a001d001700180010000e000c0268
+3208687474702f312e31002b0007062a
+2a03040303ff01000100000d00120010
+04030804040105030805050108060601
+000b00020100002300000033002b0029
+1a1a000100001d0020d3c76bef062979
+a812ce935cfb4dbe6b3a84dc5ba9226f
+23b0f34af9d1d03b4a001b0003020002
+00120000446900050003026832000000
+170015000012706b67732e7461696c73
+63616c652e636f6d002d000201010005
+00050100000000001700003a3a000100
+0015002d000000000000000000000000
+00000000000000000000000000000000
+00000000000000000000000000000000
+0000290094006f0069e76f2016f963ad
+38c8632d1f240cd75e00e25fdef295d4
+7042b26f3a9a543b1c7dc74939d77803
+20527d423ff996997bda2c6383a14f49
+219eeef8a053e90a32228df37ddbe126
+eccf6b085c93890d08341d819aea6111
+0d909f4cd6b071d9ea40618e74588a33
+90d494bbb5c3002120d5a164a16c9724
+c9ef5e540d8d6f007789a7acf9f5f16f
+bf6a1907a6782ed02b`
+
+func fakeSNIHeader() []byte {
+	b, err := hex.DecodeString(strings.Replace(tlsStart, "\n", "", -1))
+	if err != nil {
+		panic(err)
+	}
+	return b[0x34:] // trim IP + TCP header
+}
+
+func TestTCPSNIHandler(t *testing.T) {
+	h := tcpSNIHandler{
+		Allowlist: []string{"pkgs.tailscale.com"},
+		DialContext: func(ctx context.Context, network, addr string) (net.Conn, error) {
+			if network != "tcp" {
+				t.Errorf("network = %s, want %s", network, "tcp")
+			}
+			if addr != "pkgs.tailscale.com:443" {
+				t.Errorf("addr = %s, want %s", addr, "pkgs.tailscale.com:443")
+			}
+
+			c, s := memnet.NewConn("outbound", 1024)
+			go echoConnOnce(s)
+			return c, nil
+		},
+	}
+
+	cSock, sSock := memnet.NewTCPConn(netip.MustParseAddrPort("10.64.1.2:22"), netip.MustParseAddrPort("10.64.1.2:443"), 1024)
+	h.Handle(sSock)
+
+	// Fake a TLS handshake record with an SNI in it.
+	if _, err := cSock.Write(fakeSNIHeader()); err != nil {
+		t.Fatal(err)
+	}
+
+	// Test read, the other end will echo back
+	// a single stanza, which is at least the beginning of the SNI header.
+	want := fakeSNIHeader()[:5]
+	if _, err := cSock.Write(want); err != nil {
+		t.Fatal(err)
+	}
+	got := make([]byte, len(want))
+	if _, err := io.ReadAtLeast(cSock, got, len(got)); err != nil {
+		t.Fatal(err)
+	}
+	if !bytes.Equal(got, want) {
+		t.Errorf("got %q, want %q", got, want)
+	}
+}

cmd/sniproxy/server.go

@@ -0,0 +1,327 @@
+// Copyright (c) Tailscale Inc & AUTHORS
+// SPDX-License-Identifier: BSD-3-Clause
+
+package main
+
+import (
+	"expvar"
+	"log"
+	"net"
+	"net/netip"
+	"sync"
+	"time"
+
+	"golang.org/x/net/dns/dnsmessage"
+	"tailscale.com/metrics"
+	"tailscale.com/tailcfg"
+	"tailscale.com/types/appctype"
+	"tailscale.com/types/ipproto"
+	"tailscale.com/types/nettype"
+	"tailscale.com/util/clientmetric"
+	"tailscale.com/util/mak"
+)
+
+var tsMBox = dnsmessage.MustNewName("support.tailscale.com.")
+
+// target describes the predicates which route some inbound
+// traffic to the app connector to a specific handler.
+type target struct {
+	Dest     netip.Prefix
+	Matching tailcfg.ProtoPortRange
+}
+
+// Server implements an App Connector as expressed in sniproxy.
+type Server struct {
+	mu         sync.RWMutex // mu guards following fields
+	connectors map[appctype.ConfigID]connector
+}
+
+type appcMetrics struct {
+	dnsResponses   expvar.Int
+	dnsFailures    expvar.Int
+	tcpConns       expvar.Int
+	sniConns       expvar.Int
+	unhandledConns expvar.Int
+}
+
+var getMetrics = sync.OnceValue[*appcMetrics](func() *appcMetrics {
+	m := appcMetrics{}
+
+	stats := new(metrics.Set)
+	stats.Set("tls_sessions", &m.sniConns)
+	clientmetric.NewCounterFunc("sniproxy_tls_sessions", m.sniConns.Value)
+	stats.Set("tcp_sessions", &m.tcpConns)
+	clientmetric.NewCounterFunc("sniproxy_tcp_sessions", m.tcpConns.Value)
+	stats.Set("dns_responses", &m.dnsResponses)
+	clientmetric.NewCounterFunc("sniproxy_dns_responses", m.dnsResponses.Value)
+	stats.Set("dns_failed", &m.dnsFailures)
+	clientmetric.NewCounterFunc("sniproxy_dns_failed", m.dnsFailures.Value)
+	expvar.Publish("sniproxy", stats)
+
+	return &m
+})
+
+// Configure applies the provided configuration to the app connector.
+func (s *Server) Configure(cfg *appctype.AppConnectorConfig) {
+	s.mu.Lock()
+	defer s.mu.Unlock()
+	s.connectors = makeConnectorsFromConfig(cfg)
+	log.Printf("installed app connector config: %+v", s.connectors)
+}
+
+// HandleTCPFlow implements tsnet.FallbackTCPHandler.
+func (s *Server) HandleTCPFlow(src, dst netip.AddrPort) (handler func(net.Conn), intercept bool) {
+	m := getMetrics()
+	s.mu.RLock()
+	defer s.mu.RUnlock()
+
+	for _, c := range s.connectors {
+		if handler, intercept := c.handleTCPFlow(src, dst, m); intercept {
+			return handler, intercept
+		}
+	}
+
+	return nil, false
+}
+
+// HandleDNS handles a DNS request to the app connector.
+func (s *Server) HandleDNS(c nettype.ConnPacketConn) {
+	defer c.Close()
+	c.SetReadDeadline(time.Now().Add(5 * time.Second))
+	m := getMetrics()
+
+	buf := make([]byte, 1500)
+	n, err := c.Read(buf)
+	if err != nil {
+		log.Printf("HandleDNS: read failed: %v\n ", err)
+		m.dnsFailures.Add(1)
+		return
+	}
+
+	addrPortStr := c.LocalAddr().String()
+	host, _, err := net.SplitHostPort(addrPortStr)
+	if err != nil {
+		log.Printf("HandleDNS: bogus addrPort %q", addrPortStr)
+		m.dnsFailures.Add(1)
+		return
+	}
+	localAddr, err := netip.ParseAddr(host)
+	if err != nil {
+		log.Printf("HandleDNS: bogus local address %q", host)
+		m.dnsFailures.Add(1)
+		return
+	}
+
+	var msg dnsmessage.Message
+	err = msg.Unpack(buf[:n])
+	if err != nil {
+		log.Printf("HandleDNS: dnsmessage unpack failed: %v\n ", err)
+		m.dnsFailures.Add(1)
+		return
+	}
+
+	s.mu.RLock()
+	defer s.mu.RUnlock()
+	for _, connector := range s.connectors {
+		resp, err := connector.handleDNS(&msg, localAddr)
+		if err != nil {
+			log.Printf("HandleDNS: connector handling failed: %v\n", err)
+			m.dnsFailures.Add(1)
+			return
+		}
+		if len(resp) > 0 {
+			// This connector handled the DNS request
+			_, err = c.Write(resp)
+			if err != nil {
+				log.Printf("HandleDNS: write failed: %v\n", err)
+				m.dnsFailures.Add(1)
+				return
+			}
+
+			m.dnsResponses.Add(1)
+			return
+		}
+	}
+}
+
+// connector describes a logical collection of
+// services which need to be proxied.
+type connector struct {
+	Handlers map[target]handler
+}
+
+// handleTCPFlow implements tsnet.FallbackTCPHandler.
+func (c *connector) handleTCPFlow(src, dst netip.AddrPort, m *appcMetrics) (handler func(net.Conn), intercept bool) {
+	for t, h := range c.Handlers {
+		if t.Matching.Proto != 0 && t.Matching.Proto != int(ipproto.TCP) {
+			continue
+		}
+		if !t.Dest.Contains(dst.Addr()) {
+			continue
+		}
+		if !t.Matching.Ports.Contains(dst.Port()) {
+			continue
+		}
+
+		switch h.(type) {
+		case *tcpSNIHandler:
+			m.sniConns.Add(1)
+		case *tcpRoundRobinHandler:
+			m.tcpConns.Add(1)
+		default:
+			log.Printf("handleTCPFlow: unhandled handler type %T", h)
+		}
+
+		return h.Handle, true
+	}
+
+	m.unhandledConns.Add(1)
+	return nil, false
+}
+
+// handleDNS returns the DNS response to the given query. If this
+// connector is unable to handle the request, nil is returned.
+func (c *connector) handleDNS(req *dnsmessage.Message, localAddr netip.Addr) (response []byte, err error) {
+	for t, h := range c.Handlers {
+		if t.Dest.Contains(localAddr) {
+			return makeDNSResponse(req, h.ReachableOn())
+		}
+	}
+
+	// Did not match, signal 'not handled' to caller
+	return nil, nil
+}
+
+func makeDNSResponse(req *dnsmessage.Message, reachableIPs []netip.Addr) (response []byte, err error) {
+	resp := dnsmessage.NewBuilder(response,
+		dnsmessage.Header{
+			ID:            req.Header.ID,
+			Response:      true,
+			Authoritative: true,
+		})
+	resp.EnableCompression()
+
+	if len(req.Questions) == 0 {
+		response, _ = resp.Finish()
+		return response, nil
+	}
+	q := req.Questions[0]
+	err = resp.StartQuestions()
+	if err != nil {
+		return
+	}
+	resp.Question(q)
+
+	err = resp.StartAnswers()
+	if err != nil {
+		return
+	}
+
+	switch q.Type {
+	case dnsmessage.TypeAAAA:
+		for _, ip := range reachableIPs {
+			if ip.Is6() {
+				err = resp.AAAAResource(
+					dnsmessage.ResourceHeader{Name: q.Name, Class: q.Class, TTL: 120},
+					dnsmessage.AAAAResource{AAAA: ip.As16()},
+				)
+			}
+		}
+
+	case dnsmessage.TypeA:
+		for _, ip := range reachableIPs {
+			if ip.Is4() {
+				err = resp.AResource(
+					dnsmessage.ResourceHeader{Name: q.Name, Class: q.Class, TTL: 120},
+					dnsmessage.AResource{A: ip.As4()},
+				)
+			}
+		}
+
+	case dnsmessage.TypeSOA:
+		err = resp.SOAResource(
+			dnsmessage.ResourceHeader{Name: q.Name, Class: q.Class, TTL: 120},
+			dnsmessage.SOAResource{NS: q.Name, MBox: tsMBox, Serial: 2023030600,
+				Refresh: 120, Retry: 120, Expire: 120, MinTTL: 60},
+		)
+	case dnsmessage.TypeNS:
+		err = resp.NSResource(
+			dnsmessage.ResourceHeader{Name: q.Name, Class: q.Class, TTL: 120},
+			dnsmessage.NSResource{NS: tsMBox},
+		)
+	}
+
+	if err != nil {
+		return nil, err
+	}
+	return resp.Finish()
+}
+
+type handler interface {
+	// Handle handles the given socket.
+	Handle(c net.Conn)
+
+	// ReachableOn returns the IP addresses this handler is reachable on.
+	ReachableOn() []netip.Addr
+}
+
+func installDNATHandler(d *appctype.DNATConfig, out *connector) {
+	// These handlers don't actually do DNAT, they just
+	// proxy the data over the connection.
+	var dialer net.Dialer
+	dialer.Timeout = 5 * time.Second
+	h := tcpRoundRobinHandler{
+		To:           d.To,
+		DialContext:  dialer.DialContext,
+		ReachableIPs: d.Addrs,
+	}
+
+	for _, addr := range d.Addrs {
+		for _, protoPort := range d.IP {
+			t := target{
+				Dest:     netip.PrefixFrom(addr, addr.BitLen()),
+				Matching: protoPort,
+			}
+
+			mak.Set(&out.Handlers, t, handler(&h))
+		}
+	}
+}
+
+func installSNIHandler(c *appctype.SNIProxyConfig, out *connector) {
+	var dialer net.Dialer
+	dialer.Timeout = 5 * time.Second
+	h := tcpSNIHandler{
+		Allowlist:    c.AllowedDomains,
+		DialContext:  dialer.DialContext,
+		ReachableIPs: c.Addrs,
+	}
+
+	for _, addr := range c.Addrs {
+		for _, protoPort := range c.IP {
+			t := target{
+				Dest:     netip.PrefixFrom(addr, addr.BitLen()),
+				Matching: protoPort,
+			}
+
+			mak.Set(&out.Handlers, t, handler(&h))
+		}
+	}
+}
+
+func makeConnectorsFromConfig(cfg *appctype.AppConnectorConfig) map[appctype.ConfigID]connector {
+	var connectors map[appctype.ConfigID]connector
+
+	for cID, d := range cfg.DNAT {
+		c := connectors[cID]
+		installDNATHandler(&d, &c)
+		mak.Set(&connectors, cID, c)
+	}
+	for cID, d := range cfg.SNIProxy {
+		c := connectors[cID]
+		installSNIHandler(&d, &c)
+		mak.Set(&connectors, cID, c)
+	}
+
+	return connectors
+}

cmd/sniproxy/server_test.go

@@ -0,0 +1,95 @@
+// Copyright (c) Tailscale Inc & AUTHORS
+// SPDX-License-Identifier: BSD-3-Clause
+
+package main
+
+import (
+	"net/netip"
+	"testing"
+
+	"github.com/google/go-cmp/cmp"
+	"github.com/google/go-cmp/cmp/cmpopts"
+	"tailscale.com/tailcfg"
+	"tailscale.com/types/appctype"
+)
+
+func TestMakeConnectorsFromConfig(t *testing.T) {
+	tcs := []struct {
+		name  string
+		input *appctype.AppConnectorConfig
+		want  map[appctype.ConfigID]connector
+	}{
+		{
+			"empty",
+			&appctype.AppConnectorConfig{},
+			nil,
+		},
+		{
+			"DNAT",
+			&appctype.AppConnectorConfig{
+				DNAT: map[appctype.ConfigID]appctype.DNATConfig{
+					"swiggity_swooty": {
+						Addrs: []netip.Addr{netip.MustParseAddr("100.64.0.1"), netip.MustParseAddr("fd7a:115c:a1e0::1")},
+						To:    []string{"example.org"},
+						IP:    []tailcfg.ProtoPortRange{{Proto: 0, Ports: tailcfg.PortRange{First: 0, Last: 65535}}},
+					},
+				},
+			},
+			map[appctype.ConfigID]connector{
+				"swiggity_swooty": {
+					Handlers: map[target]handler{
+						{
+							Dest:     netip.MustParsePrefix("100.64.0.1/32"),
+							Matching: tailcfg.ProtoPortRange{Proto: 0, Ports: tailcfg.PortRange{First: 0, Last: 65535}},
+						}: &tcpRoundRobinHandler{To: []string{"example.org"}, ReachableIPs: []netip.Addr{netip.MustParseAddr("100.64.0.1"), netip.MustParseAddr("fd7a:115c:a1e0::1")}},
+						{
+							Dest:     netip.MustParsePrefix("fd7a:115c:a1e0::1/128"),
+							Matching: tailcfg.ProtoPortRange{Proto: 0, Ports: tailcfg.PortRange{First: 0, Last: 65535}},
+						}: &tcpRoundRobinHandler{To: []string{"example.org"}, ReachableIPs: []netip.Addr{netip.MustParseAddr("100.64.0.1"), netip.MustParseAddr("fd7a:115c:a1e0::1")}},
+					},
+				},
+			},
+		},
+		{
+			"SNIProxy",
+			&appctype.AppConnectorConfig{
+				SNIProxy: map[appctype.ConfigID]appctype.SNIProxyConfig{
+					"swiggity_swooty": {
+						Addrs:          []netip.Addr{netip.MustParseAddr("100.64.0.1"), netip.MustParseAddr("fd7a:115c:a1e0::1")},
+						AllowedDomains: []string{"example.org"},
+						IP:             []tailcfg.ProtoPortRange{{Proto: 0, Ports: tailcfg.PortRange{First: 0, Last: 65535}}},
+					},
+				},
+			},
+			map[appctype.ConfigID]connector{
+				"swiggity_swooty": {
+					Handlers: map[target]handler{
+						{
+							Dest:     netip.MustParsePrefix("100.64.0.1/32"),
+							Matching: tailcfg.ProtoPortRange{Proto: 0, Ports: tailcfg.PortRange{First: 0, Last: 65535}},
+						}: &tcpSNIHandler{Allowlist: []string{"example.org"}, ReachableIPs: []netip.Addr{netip.MustParseAddr("100.64.0.1"), netip.MustParseAddr("fd7a:115c:a1e0::1")}},
+						{
+							Dest:     netip.MustParsePrefix("fd7a:115c:a1e0::1/128"),
+							Matching: tailcfg.ProtoPortRange{Proto: 0, Ports: tailcfg.PortRange{First: 0, Last: 65535}},
+						}: &tcpSNIHandler{Allowlist: []string{"example.org"}, ReachableIPs: []netip.Addr{netip.MustParseAddr("100.64.0.1"), netip.MustParseAddr("fd7a:115c:a1e0::1")}},
+					},
+				},
+			},
+		},
+	}
+
+	for _, tc := range tcs {
+		t.Run(tc.name, func(t *testing.T) {
+			connectors := makeConnectorsFromConfig(tc.input)
+
+			if diff := cmp.Diff(connectors, tc.want,
+				cmpopts.IgnoreFields(tcpRoundRobinHandler{}, "DialContext"),
+				cmpopts.IgnoreFields(tcpSNIHandler{}, "DialContext"),
+				cmp.Comparer(func(x, y netip.Addr) bool {
+					return x == y
+				})); diff != "" {
+				t.Fatalf("mismatch (-want +got):\n%s", diff)
+			}
+		})
+	}
+}

cmd/sniproxy/sniproxy.go

@@ -10,31 +10,31 @@ package main
 import (
 	"context"
 	"errors"
-	"expvar"
 	"flag"
 	"fmt"
 	"log"
 	"net"
 	"net/http"
+	"net/netip"
 	"os"
+	"sort"
 	"strconv"
 	"strings"
-	"time"
 
 	"github.com/peterbourgon/ff/v3"
-	"golang.org/x/net/dns/dnsmessage"
-	"inet.af/tcpproxy"
 	"tailscale.com/client/tailscale"
 	"tailscale.com/hostinfo"
-	"tailscale.com/metrics"
-	"tailscale.com/net/netutil"
+	"tailscale.com/ipn"
+	"tailscale.com/tailcfg"
 	"tailscale.com/tsnet"
 	"tailscale.com/tsweb"
+	"tailscale.com/types/appctype"
+	"tailscale.com/types/ipproto"
 	"tailscale.com/types/nettype"
-	"tailscale.com/util/clientmetric"
+	"tailscale.com/util/mak"
 )
 
-var tsMBox = dnsmessage.MustNewName("support.tailscale.com.")
+const configCapKey = "tailscale.com/sniproxy"
 
 // portForward is the state for a single port forwarding entry, as passed to the --forward flag.
 type portForward struct {
@@ -68,6 +68,7 @@ func parseForward(value string) (*portForward, error) {
 }
 
 func main() {
+	// Parse flags
 	fs := flag.NewFlagSet("sniproxy", flag.ContinueOnError)
 	var (
 		ports        = fs.String("ports", "443", "comma-separated list of ports to proxy")
@@ -75,334 +76,216 @@ func main() {
 		wgPort       = fs.Int("wg-listen-port", 0, "UDP port to listen on for WireGuard and peer-to-peer traffic; 0 means automatically select")
 		promoteHTTPS = fs.Bool("promote-https", true, "promote HTTP to HTTPS")
 		debugPort    = fs.Int("debug-port", 8893, "Listening port for debug/metrics endpoint")
+		hostname     = fs.String("hostname", "", "Hostname to register the service under")
 	)
-
 	err := ff.Parse(fs, os.Args[1:], ff.WithEnvVarPrefix("TS_APPC"))
 	if err != nil {
 		log.Fatal("ff.Parse")
 	}
-	if *ports == "" {
-		log.Fatal("no ports")
-	}
 
+	var ts tsnet.Server
+	defer ts.Close()
+
+	ctx, cancel := context.WithCancel(context.Background())
+	defer cancel()
+	run(ctx, &ts, *wgPort, *hostname, *promoteHTTPS, *debugPort, *ports, *forwards)
+}
+
+// run actually runs the sniproxy. Its separate from main() to assist in testing.
+func run(ctx context.Context, ts *tsnet.Server, wgPort int, hostname string, promoteHTTPS bool, debugPort int, ports, forwards string) {
+	// Wire up Tailscale node + app connector server
 	hostinfo.SetApp("sniproxy")
+	var s sniproxy
+	s.ts = ts
 
-	var s server
-	s.ts.Port = uint16(*wgPort)
-	defer s.ts.Close()
+	s.ts.Port = uint16(wgPort)
+	s.ts.Hostname = hostname
 
 	lc, err := s.ts.LocalClient()
 	if err != nil {
-		log.Fatal(err)
+		log.Fatalf("LocalClient() failed: %v", err)
 	}
 	s.lc = lc
-	s.initMetrics()
+	s.ts.RegisterFallbackTCPHandler(s.srv.HandleTCPFlow)
 
-	for _, portStr := range strings.Split(*ports, ",") {
-		ln, err := s.ts.Listen("tcp", ":"+portStr)
+	// Start special-purpose listeners: dns, http promotion, debug server
+	ln, err := s.ts.Listen("udp", ":53")
+	if err != nil {
+		log.Fatalf("failed listening on port 53: %v", err)
+	}
+	defer ln.Close()
+	go s.serveDNS(ln)
+	if promoteHTTPS {
+		ln, err := s.ts.Listen("tcp", ":80")
 		if err != nil {
-			log.Fatal(err)
+			log.Fatalf("failed listening on port 80: %v", err)
 		}
-		log.Printf("Serving on port %v ...", portStr)
-		go s.serve(ln)
+		defer ln.Close()
+		log.Printf("Promoting HTTP to HTTPS ...")
+		go s.promoteHTTPS(ln)
+	}
+	if debugPort != 0 {
+		mux := http.NewServeMux()
+		tsweb.Debugger(mux)
+		dln, err := s.ts.Listen("tcp", fmt.Sprintf(":%d", debugPort))
+		if err != nil {
+			log.Fatalf("failed listening on debug port: %v", err)
+		}
+		defer dln.Close()
+		go func() {
+			log.Fatalf("debug serve: %v", http.Serve(dln, mux))
+		}()
 	}
 
-	for _, forwStr := range strings.Split(*forwards, ",") {
+	// Finally, start mainloop to configure app connector based on information
+	// in the netmap.
+	// We set the NotifyInitialNetMap flag so we will always get woken with the
+	// current netmap, before only being woken on changes.
+	bus, err := lc.WatchIPNBus(ctx, ipn.NotifyWatchEngineUpdates|ipn.NotifyInitialNetMap|ipn.NotifyNoPrivateKeys)
+	if err != nil {
+		log.Fatalf("watching IPN bus: %v", err)
+	}
+	defer bus.Close()
+	for {
+		msg, err := bus.Next()
+		if err != nil {
+			if errors.Is(err, context.Canceled) {
+				return
+			}
+			log.Fatalf("reading IPN bus: %v", err)
+		}
+
+		// NetMap contains app-connector configuration
+		if nm := msg.NetMap; nm != nil && nm.SelfNode.Valid() {
+			sn := nm.SelfNode.AsStruct()
+
+			var c appctype.AppConnectorConfig
+			nmConf, err := tailcfg.UnmarshalNodeCapJSON[appctype.AppConnectorConfig](sn.CapMap, configCapKey)
+			if err != nil {
+				log.Printf("failed to read app connector configuration from coordination server: %v", err)
+			} else if len(nmConf) > 0 {
+				c = nmConf[0]
+			}
+
+			if c.AdvertiseRoutes {
+				if err := s.advertiseRoutesFromConfig(ctx, &c); err != nil {
+					log.Printf("failed to advertise routes: %v", err)
+				}
+			}
+
+			// Backwards compatibility: combine any configuration from control with flags specified
+			// on the command line. This is intentionally done after we advertise any routes
+			// because its never correct to advertise the nodes native IP addresses.
+			s.mergeConfigFromFlags(&c, ports, forwards)
+			s.srv.Configure(&c)
+		}
+	}
+}
+
+type sniproxy struct {
+	srv Server
+	ts  *tsnet.Server
+	lc  *tailscale.LocalClient
+}
+
+func (s *sniproxy) advertiseRoutesFromConfig(ctx context.Context, c *appctype.AppConnectorConfig) error {
+	// Collect the set of addresses to advertise, using a map
+	// to avoid duplicate entries.
+	addrs := map[netip.Addr]struct{}{}
+	for _, c := range c.SNIProxy {
+		for _, ip := range c.Addrs {
+			addrs[ip] = struct{}{}
+		}
+	}
+	for _, c := range c.DNAT {
+		for _, ip := range c.Addrs {
+			addrs[ip] = struct{}{}
+		}
+	}
+
+	var routes []netip.Prefix
+	for a := range addrs {
+		routes = append(routes, netip.PrefixFrom(a, a.BitLen()))
+	}
+	sort.SliceStable(routes, func(i, j int) bool {
+		return routes[i].Addr().Less(routes[j].Addr()) // determinism r us
+	})
+
+	_, err := s.lc.EditPrefs(ctx, &ipn.MaskedPrefs{
+		Prefs: ipn.Prefs{
+			AdvertiseRoutes: routes,
+		},
+		AdvertiseRoutesSet: true,
+	})
+	return err
+}
+
+func (s *sniproxy) mergeConfigFromFlags(out *appctype.AppConnectorConfig, ports, forwards string) {
+	ip4, ip6 := s.ts.TailscaleIPs()
+
+	sniConfigFromFlags := appctype.SNIProxyConfig{
+		Addrs: []netip.Addr{ip4, ip6},
+	}
+	if ports != "" {
+		for _, portStr := range strings.Split(ports, ",") {
+			port, err := strconv.ParseUint(portStr, 10, 16)
+			if err != nil {
+				log.Fatalf("invalid port: %s", portStr)
+			}
+			sniConfigFromFlags.IP = append(sniConfigFromFlags.IP, tailcfg.ProtoPortRange{
+				Proto: int(ipproto.TCP),
+				Ports: tailcfg.PortRange{First: uint16(port), Last: uint16(port)},
+			})
+		}
+	}
+
+	var forwardConfigFromFlags []appctype.DNATConfig
+	for _, forwStr := range strings.Split(forwards, ",") {
 		if forwStr == "" {
 			continue
 		}
 		forw, err := parseForward(forwStr)
 		if err != nil {
-			log.Fatal(err)
+			log.Printf("invalid forwarding spec: %v", err)
+			continue
 		}
 
-		ln, err := s.ts.Listen("tcp", ":"+strconv.Itoa(forw.Port))
-		if err != nil {
-			log.Fatal(err)
-		}
-		log.Printf("Serving on port %d to %s...", forw.Port, forw.Destination)
-
-		// Add an entry to the expvar LabelMap for Prometheus metrics,
-		// and create a clientmetric to report that same value.
-		service := portNumberToName(forw)
-		s.numTCPsessions.SetInt64(service, 0)
-		metric := fmt.Sprintf("sniproxy_tcp_sessions_%s", service)
-		clientmetric.NewCounterFunc(metric, func() int64 {
-			return s.numTCPsessions.Get(service).Value()
+		forwardConfigFromFlags = append(forwardConfigFromFlags, appctype.DNATConfig{
+			Addrs: []netip.Addr{ip4, ip6},
+			To:    []string{forw.Destination},
+			IP: []tailcfg.ProtoPortRange{
+				{
+					Proto: int(ipproto.TCP),
+					Ports: tailcfg.PortRange{First: uint16(forw.Port), Last: uint16(forw.Port)},
+				},
+			},
 		})
-
-		go s.forward(ln, forw)
 	}
 
-	ln, err := s.ts.Listen("udp", ":53")
-	if err != nil {
-		log.Fatal(err)
-	}
-	go s.serveDNS(ln)
-
-	if *promoteHTTPS {
-		ln, err := s.ts.Listen("tcp", ":80")
-		if err != nil {
-			log.Fatal(err)
-		}
-		log.Printf("Promoting HTTP to HTTPS ...")
-		go s.promoteHTTPS(ln)
+	if len(forwardConfigFromFlags) == 0 && len(sniConfigFromFlags.IP) == 0 {
+		return // no config specified on the command line
 	}
 
-	if *debugPort != 0 {
-		mux := http.NewServeMux()
-		tsweb.Debugger(mux)
-		dln, err := s.ts.Listen("tcp", fmt.Sprintf(":%d", *debugPort))
-		if err != nil {
-			log.Fatal(err)
-		}
-		go func() {
-			log.Fatal(http.Serve(dln, mux))
-		}()
+	mak.Set(&out.SNIProxy, "flags", sniConfigFromFlags)
+	for i, forward := range forwardConfigFromFlags {
+		mak.Set(&out.DNAT, appctype.ConfigID(fmt.Sprintf("flags_%d", i)), forward)
 	}
-
-	select {}
 }
 
-type server struct {
-	ts tsnet.Server
-	lc *tailscale.LocalClient
-
-	numTLSsessions expvar.Int
-	numTCPsessions *metrics.LabelMap
-	numBadAddrPort expvar.Int
-	dnsResponses   expvar.Int
-	dnsFailures    expvar.Int
-	httpPromoted   expvar.Int
-}
-
-func (s *server) serve(ln net.Listener) {
+func (s *sniproxy) serveDNS(ln net.Listener) {
 	for {
 		c, err := ln.Accept()
 		if err != nil {
-			log.Fatal(err)
+			log.Printf("serveDNS accept: %v", err)
+			return
 		}
-		go s.serveConn(c)
+		go s.srv.HandleDNS(c.(nettype.ConnPacketConn))
 	}
 }
 
-func (s *server) forward(ln net.Listener, forw *portForward) {
-	for {
-		c, err := ln.Accept()
-		if err != nil {
-			log.Fatal(err)
-		}
-		go s.forwardConn(c, forw)
-	}
-}
-
-func (s *server) serveDNS(ln net.Listener) {
-	for {
-		c, err := ln.Accept()
-		if err != nil {
-			log.Fatal(err)
-		}
-		go s.serveDNSConn(c.(nettype.ConnPacketConn))
-	}
-}
-
-func (s *server) serveDNSConn(c nettype.ConnPacketConn) {
-	defer c.Close()
-	c.SetReadDeadline(time.Now().Add(5 * time.Second))
-	buf := make([]byte, 1500)
-	n, err := c.Read(buf)
-	if err != nil {
-		log.Printf("c.Read failed: %v\n ", err)
-		s.dnsFailures.Add(1)
-		return
-	}
-
-	var msg dnsmessage.Message
-	err = msg.Unpack(buf[:n])
-	if err != nil {
-		log.Printf("dnsmessage unpack failed: %v\n ", err)
-		s.dnsFailures.Add(1)
-		return
-	}
-
-	buf, err = s.dnsResponse(&msg)
-	if err != nil {
-		log.Printf("s.dnsResponse failed: %v\n", err)
-		s.dnsFailures.Add(1)
-		return
-	}
-
-	_, err = c.Write(buf)
-	if err != nil {
-		log.Printf("c.Write failed: %v\n", err)
-		s.dnsFailures.Add(1)
-		return
-	}
-
-	s.dnsResponses.Add(1)
-}
-
-func (s *server) serveConn(c net.Conn) {
-	addrPortStr := c.LocalAddr().String()
-	_, port, err := net.SplitHostPort(addrPortStr)
-	if err != nil {
-		log.Printf("bogus addrPort %q", addrPortStr)
-		s.numBadAddrPort.Add(1)
-		c.Close()
-		return
-	}
-
-	var dialer net.Dialer
-	dialer.Timeout = 5 * time.Second
-
-	var p tcpproxy.Proxy
-	p.ListenFunc = func(net, laddr string) (net.Listener, error) {
-		return netutil.NewOneConnListener(c, nil), nil
-	}
-	p.AddSNIRouteFunc(addrPortStr, func(ctx context.Context, sniName string) (t tcpproxy.Target, ok bool) {
-		s.numTLSsessions.Add(1)
-		return &tcpproxy.DialProxy{
-			Addr:        net.JoinHostPort(sniName, port),
-			DialContext: dialer.DialContext,
-		}, true
-	})
-	p.Start()
-}
-
-// portNumberToName returns a human-readable name for several port numbers commonly forwarded,
-// and "tcp###" for everything else. It is used for metric label names.
-func portNumberToName(forw *portForward) string {
-	switch forw.Port {
-	case 22:
-		return "ssh"
-	case 1433:
-		return "sqlserver"
-	case 3306:
-		return "mysql"
-	case 3389:
-		return "rdp"
-	case 5432:
-		return "postgres"
-	default:
-		return fmt.Sprintf("%s%d", forw.Proto, forw.Port)
-	}
-}
-
-// forwardConn sets up a forwarder for a TCP connection. It does not inspect of the data
-// like the SNI forwarding does, it merely forwards all data to the destination specified
-// in the --forward=tcp/22/github.com argument.
-func (s *server) forwardConn(c net.Conn, forw *portForward) {
-	addrPortStr := c.LocalAddr().String()
-
-	var dialer net.Dialer
-	dialer.Timeout = 30 * time.Second
-
-	var p tcpproxy.Proxy
-	p.ListenFunc = func(net, laddr string) (net.Listener, error) {
-		return netutil.NewOneConnListener(c, nil), nil
-	}
-
-	dial := &tcpproxy.DialProxy{
-		Addr:        fmt.Sprintf("%s:%d", forw.Destination, forw.Port),
-		DialContext: dialer.DialContext,
-	}
-
-	p.AddRoute(addrPortStr, dial)
-	s.numTCPsessions.Add(portNumberToName(forw), 1)
-	p.Start()
-}
-
-func (s *server) dnsResponse(req *dnsmessage.Message) (buf []byte, err error) {
-	resp := dnsmessage.NewBuilder(buf,
-		dnsmessage.Header{
-			ID:            req.Header.ID,
-			Response:      true,
-			Authoritative: true,
-		})
-	resp.EnableCompression()
-
-	if len(req.Questions) == 0 {
-		buf, _ = resp.Finish()
-		return
-	}
-
-	q := req.Questions[0]
-	err = resp.StartQuestions()
-	if err != nil {
-		return
-	}
-	resp.Question(q)
-
-	ip4, ip6 := s.ts.TailscaleIPs()
-	err = resp.StartAnswers()
-	if err != nil {
-		return
-	}
-
-	switch q.Type {
-	case dnsmessage.TypeAAAA:
-		err = resp.AAAAResource(
-			dnsmessage.ResourceHeader{Name: q.Name, Class: q.Class, TTL: 120},
-			dnsmessage.AAAAResource{AAAA: ip6.As16()},
-		)
-
-	case dnsmessage.TypeA:
-		err = resp.AResource(
-			dnsmessage.ResourceHeader{Name: q.Name, Class: q.Class, TTL: 120},
-			dnsmessage.AResource{A: ip4.As4()},
-		)
-	case dnsmessage.TypeSOA:
-		err = resp.SOAResource(
-			dnsmessage.ResourceHeader{Name: q.Name, Class: q.Class, TTL: 120},
-			dnsmessage.SOAResource{NS: q.Name, MBox: tsMBox, Serial: 2023030600,
-				Refresh: 120, Retry: 120, Expire: 120, MinTTL: 60},
-		)
-	case dnsmessage.TypeNS:
-		err = resp.NSResource(
-			dnsmessage.ResourceHeader{Name: q.Name, Class: q.Class, TTL: 120},
-			dnsmessage.NSResource{NS: tsMBox},
-		)
-	}
-
-	if err != nil {
-		return
-	}
-
-	return resp.Finish()
-}
-
-func (s *server) promoteHTTPS(ln net.Listener) {
+func (s *sniproxy) promoteHTTPS(ln net.Listener) {
 	err := http.Serve(ln, http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
-		s.httpPromoted.Add(1)
 		http.Redirect(w, r, "https://"+r.Host+r.RequestURI, http.StatusFound)
 	}))
 	log.Fatalf("promoteHTTPS http.Serve: %v", err)
 }
-
-// initMetrics sets up local prometheus metrics, and creates clientmetrics to report those
-// same counters.
-func (s *server) initMetrics() {
-	stats := new(metrics.Set)
-
-	stats.Set("tls_sessions", &s.numTLSsessions)
-	clientmetric.NewCounterFunc("sniproxy_tls_sessions", s.numTLSsessions.Value)
-
-	s.numTCPsessions = &metrics.LabelMap{Label: "proto"}
-	stats.Set("tcp_sessions", s.numTCPsessions)
-	// clientmetric doesn't have a good way to implement a Map type.
-	// We create clientmetrics dynamically when parsing the --forwards argument
-
-	stats.Set("bad_addrport", &s.numBadAddrPort)
-	clientmetric.NewCounterFunc("sniproxy_bad_addrport", s.numBadAddrPort.Value)
-
-	stats.Set("dns_responses", &s.dnsResponses)
-	clientmetric.NewCounterFunc("sniproxy_dns_responses", s.dnsResponses.Value)
-
-	stats.Set("dns_failed", &s.dnsFailures)
-	clientmetric.NewCounterFunc("sniproxy_dns_failed", s.dnsFailures.Value)
-
-	stats.Set("http_promoted", &s.httpPromoted)
-	clientmetric.NewCounterFunc("sniproxy_http_promoted", s.httpPromoted.Value)
-
-	expvar.Publish("sniproxy", stats)
-}

cmd/sniproxy/sniproxy_test.go

@@ -4,10 +4,30 @@
 package main
 
 import (
+	"context"
+	"encoding/json"
+	"flag"
+	"fmt"
+	"net"
+	"net/http/httptest"
+	"net/netip"
+	"os"
+	"path/filepath"
 	"strings"
 	"testing"
+	"time"
 
 	"github.com/google/go-cmp/cmp"
+	"tailscale.com/ipn/store/mem"
+	"tailscale.com/net/netns"
+	"tailscale.com/tailcfg"
+	"tailscale.com/tsnet"
+	"tailscale.com/tstest/integration"
+	"tailscale.com/tstest/integration/testcontrol"
+	"tailscale.com/types/appctype"
+	"tailscale.com/types/ipproto"
+	"tailscale.com/types/key"
+	"tailscale.com/types/logger"
 )
 
 func TestPortForwardingArguments(t *testing.T) {
@@ -35,3 +55,169 @@ func TestPortForwardingArguments(t *testing.T) {
 		}
 	}
 }
+
+var verboseDERP = flag.Bool("verbose-derp", false, "if set, print DERP and STUN logs")
+var verboseNodes = flag.Bool("verbose-nodes", false, "if set, print tsnet.Server logs")
+
+func startControl(t *testing.T) (control *testcontrol.Server, controlURL string) {
+	// Corp#4520: don't use netns for tests.
+	netns.SetEnabled(false)
+	t.Cleanup(func() {
+		netns.SetEnabled(true)
+	})
+
+	derpLogf := logger.Discard
+	if *verboseDERP {
+		derpLogf = t.Logf
+	}
+	derpMap := integration.RunDERPAndSTUN(t, derpLogf, "127.0.0.1")
+	control = &testcontrol.Server{
+		DERPMap: derpMap,
+		DNSConfig: &tailcfg.DNSConfig{
+			Proxied: true,
+		},
+		MagicDNSDomain: "tail-scale.ts.net",
+	}
+	control.HTTPTestServer = httptest.NewUnstartedServer(control)
+	control.HTTPTestServer.Start()
+	t.Cleanup(control.HTTPTestServer.Close)
+	controlURL = control.HTTPTestServer.URL
+	t.Logf("testcontrol listening on %s", controlURL)
+	return control, controlURL
+}
+
+func startNode(t *testing.T, ctx context.Context, controlURL, hostname string) (*tsnet.Server, key.NodePublic, netip.Addr) {
+	t.Helper()
+
+	tmp := filepath.Join(t.TempDir(), hostname)
+	os.MkdirAll(tmp, 0755)
+	s := &tsnet.Server{
+		Dir:        tmp,
+		ControlURL: controlURL,
+		Hostname:   hostname,
+		Store:      new(mem.Store),
+		Ephemeral:  true,
+	}
+	if !*verboseNodes {
+		s.Logf = logger.Discard
+	}
+	t.Cleanup(func() { s.Close() })
+
+	status, err := s.Up(ctx)
+	if err != nil {
+		t.Fatal(err)
+	}
+	return s, status.Self.PublicKey, status.TailscaleIPs[0]
+}
+
+func TestSNIProxyWithNetmapConfig(t *testing.T) {
+	c, controlURL := startControl(t)
+	ctx, cancel := context.WithTimeout(context.Background(), 30*time.Second)
+	defer cancel()
+
+	// Create a listener to proxy connections to.
+	ln, err := net.Listen("tcp", "127.0.0.1:0")
+	if err != nil {
+		t.Fatal(err)
+	}
+	defer ln.Close()
+
+	// Start sniproxy
+	sni, nodeKey, ip := startNode(t, ctx, controlURL, "snitest")
+	go run(ctx, sni, 0, sni.Hostname, false, 0, "", "")
+
+	// Configure the mock coordination server to send down app connector config.
+	config := &appctype.AppConnectorConfig{
+		DNAT: map[appctype.ConfigID]appctype.DNATConfig{
+			"nic_test": {
+				Addrs: []netip.Addr{ip},
+				To:    []string{"127.0.0.1"},
+				IP: []tailcfg.ProtoPortRange{
+					{
+						Proto: int(ipproto.TCP),
+						Ports: tailcfg.PortRange{First: uint16(ln.Addr().(*net.TCPAddr).Port), Last: uint16(ln.Addr().(*net.TCPAddr).Port)},
+					},
+				},
+			},
+		},
+	}
+	b, err := json.Marshal(config)
+	if err != nil {
+		t.Fatal(err)
+	}
+	c.SetNodeCapMap(nodeKey, tailcfg.NodeCapMap{
+		configCapKey: []tailcfg.RawMessage{tailcfg.RawMessage(b)},
+	})
+
+	// Lets spin up a second node (to represent the client).
+	client, _, _ := startNode(t, ctx, controlURL, "client")
+
+	// Make sure that the sni node has received its config.
+	l, err := sni.LocalClient()
+	if err != nil {
+		t.Fatal(err)
+	}
+	gotConfigured := false
+	for i := 0; i < 100; i++ {
+		s, err := l.StatusWithoutPeers(ctx)
+		if err != nil {
+			t.Fatal(err)
+		}
+		if len(s.Self.CapMap) > 0 {
+			gotConfigured = true
+			break // we got it
+		}
+		time.Sleep(10 * time.Millisecond)
+	}
+	if !gotConfigured {
+		t.Error("sni node never received its configuration from the coordination server!")
+	}
+
+	// Lets make the client open a connection to the sniproxy node, and
+	// make sure it results in a connection to our test listener.
+	w, err := client.Dial(ctx, "tcp", fmt.Sprintf("%s:%d", ip, ln.Addr().(*net.TCPAddr).Port))
+	if err != nil {
+		t.Fatal(err)
+	}
+	defer w.Close()
+
+	r, err := ln.Accept()
+	if err != nil {
+		t.Fatal(err)
+	}
+	r.Close()
+}
+
+func TestSNIProxyWithFlagConfig(t *testing.T) {
+	_, controlURL := startControl(t)
+	ctx, cancel := context.WithTimeout(context.Background(), 30*time.Second)
+	defer cancel()
+
+	// Create a listener to proxy connections to.
+	ln, err := net.Listen("tcp", "127.0.0.1:0")
+	if err != nil {
+		t.Fatal(err)
+	}
+	defer ln.Close()
+
+	// Start sniproxy
+	sni, _, ip := startNode(t, ctx, controlURL, "snitest")
+	go run(ctx, sni, 0, sni.Hostname, false, 0, "", fmt.Sprintf("tcp/%d/localhost", ln.Addr().(*net.TCPAddr).Port))
+
+	// Lets spin up a second node (to represent the client).
+	client, _, _ := startNode(t, ctx, controlURL, "client")
+
+	// Lets make the client open a connection to the sniproxy node, and
+	// make sure it results in a connection to our test listener.
+	w, err := client.Dial(ctx, "tcp", fmt.Sprintf("%s:%d", ip, ln.Addr().(*net.TCPAddr).Port))
+	if err != nil {
+		t.Fatal(err)
+	}
+	defer w.Close()
+
+	r, err := ln.Accept()
+	if err != nil {
+		t.Fatal(err)
+	}
+	r.Close()
+}

cmd/tailscale/cli/cli_test.go

@@ -810,6 +810,9 @@ func TestPrefFlagMapping(t *testing.T) {
 		case "Egg":
 			// Not applicable.
 			continue
+		case "RunWebClient":
+			// TODO(tailscale/corp#14335): Currently behind a feature flag.
+			continue
 		}
 		t.Errorf("unexpected new ipn.Pref field %q is not handled by up.go (see addPrefFlagMapping and checkForAccidentalSettingReverts)", prefName)
 	}
@@ -890,6 +893,7 @@ func TestUpdatePrefs(t *testing.T) {
 				AdvertiseRoutesSet:        true,
 				AdvertiseTagsSet:          true,
 				AllowSingleHostsSet:       true,
+				AppConnectorSet:           true,
 				ControlURLSet:             true,
 				CorpDNSSet:                true,
 				ExitNodeAllowLANAccessSet: true,
@@ -1128,6 +1132,49 @@ func TestUpdatePrefs(t *testing.T) {
 			wantJustEditMP: nil,
 			env:            upCheckEnv{backendState: "Running"},
 		},
+		{
+			name:  "advertise_connector",
+			flags: []string{"--advertise-connector"},
+			curPrefs: &ipn.Prefs{
+				ControlURL:       ipn.DefaultControlURL,
+				AllowSingleHosts: true,
+				CorpDNS:          true,
+				NetfilterMode:    preftype.NetfilterOn,
+			},
+			wantJustEditMP: &ipn.MaskedPrefs{
+				AppConnectorSet: true,
+				WantRunningSet:  true,
+			},
+			env: upCheckEnv{backendState: "Running"},
+			checkUpdatePrefsMutations: func(t *testing.T, newPrefs *ipn.Prefs) {
+				if !newPrefs.AppConnector.Advertise {
+					t.Errorf("prefs.AppConnector.Advertise not set")
+				}
+			},
+		},
+		{
+			name:  "no_advertise_connector",
+			flags: []string{"--advertise-connector=false"},
+			curPrefs: &ipn.Prefs{
+				ControlURL:       ipn.DefaultControlURL,
+				AllowSingleHosts: true,
+				CorpDNS:          true,
+				NetfilterMode:    preftype.NetfilterOn,
+				AppConnector: ipn.AppConnectorPrefs{
+					Advertise: true,
+				},
+			},
+			wantJustEditMP: &ipn.MaskedPrefs{
+				AppConnectorSet: true,
+				WantRunningSet:  true,
+			},
+			env: upCheckEnv{backendState: "Running"},
+			checkUpdatePrefsMutations: func(t *testing.T, newPrefs *ipn.Prefs) {
+				if newPrefs.AppConnector.Advertise {
+					t.Errorf("prefs.AppConnector.Advertise not unset")
+				}
+			},
+		},
 	}
 	for _, tt := range tests {
 		t.Run(tt.name, func(t *testing.T) {

cmd/tailscale/cli/debug.go

@@ -139,11 +139,22 @@ var debugCmd = &ffcli.Command{
 			Exec:      localAPIAction("break-derp-conns"),
 			ShortHelp: "break any open DERP connections from the daemon",
 		},
+		{
+			Name:      "pick-new-derp",
+			Exec:      localAPIAction("pick-new-derp"),
+			ShortHelp: "switch to some other random DERP home region for a short time",
+		},
 		{
 			Name:      "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",
+			Exec:      reloadConfig,
+			ShortHelp: "reload config",
+		},
 		{
 			Name:      "control-knobs",
 			Exec:      debugControlKnobs,
@@ -446,6 +457,20 @@ func localAPIAction(action string) func(context.Context, []string) error {
 	}
 }
 
+func reloadConfig(ctx context.Context, args []string) error {
+	ok, err := localClient.ReloadConfig(ctx)
+	if err != nil {
+		return err
+	}
+	if ok {
+		printf("config reloaded\n")
+		return nil
+	}
+	printf("config mode not in use\n")
+	os.Exit(1)
+	panic("unreachable")
+}
+
 func runEnv(ctx context.Context, args []string) error {
 	for _, e := range os.Environ() {
 		outln(e)

cmd/tailscale/cli/file.go

@@ -18,7 +18,6 @@ import (
 	"path"
 	"path/filepath"
 	"strings"
-	"sync"
 	"sync/atomic"
 	"time"
 	"unicode/utf8"
@@ -29,8 +28,11 @@ import (
 	"tailscale.com/client/tailscale/apitype"
 	"tailscale.com/envknob"
 	"tailscale.com/net/tsaddr"
+	"tailscale.com/syncs"
 	"tailscale.com/tailcfg"
+	tsrate "tailscale.com/tstime/rate"
 	"tailscale.com/util/quarantine"
+	"tailscale.com/util/truncate"
 	"tailscale.com/version"
 )
 
@@ -52,12 +54,12 @@ var fileCmd = &ffcli.Command{
 
 type countingReader struct {
 	io.Reader
-	n atomic.Uint64
+	n atomic.Int64
 }
 
 func (c *countingReader) Read(buf []byte) (int, error) {
 	n, err := c.Reader.Read(buf)
-	c.n.Add(uint64(n))
+	c.n.Add(int64(n))
 	return n, err
 }
 
@@ -170,75 +172,100 @@ func runCp(ctx context.Context, args []string) error {
 			log.Printf("sending %q to %v/%v/%v ...", name, target, ip, stableID)
 		}
 
-		var (
-			done = make(chan struct{}, 1)
-			wg   sync.WaitGroup
-		)
+		var group syncs.WaitGroup
+		ctxProgress, cancelProgress := context.WithCancel(ctx)
+		defer cancelProgress()
 		if isatty.IsTerminal(os.Stderr.Fd()) {
-			go printProgress(&wg, done, fileContents, name, contentLength)
-			wg.Add(1)
+			group.Go(func() { progressPrinter(ctxProgress, name, fileContents.n.Load, contentLength) })
 		}
 
 		err := localClient.PushFile(ctx, stableID, contentLength, name, fileContents)
+		cancelProgress()
+		group.Wait() // wait for progress printer to stop before reporting the error
 		if err != nil {
 			return err
 		}
 		if cpArgs.verbose {
 			log.Printf("sent %q", name)
 		}
-		done <- struct{}{}
-		wg.Wait()
 	}
 	return nil
 }
 
-const vtRestartLine = "\r\x1b[K"
+func progressPrinter(ctx context.Context, name string, contentCount func() int64, contentLength int64) {
+	var rateValueFast, rateValueSlow tsrate.Value
+	rateValueFast.HalfLife = 1 * time.Second  // fast response for rate measurement
+	rateValueSlow.HalfLife = 10 * time.Second // slow response for ETA measurement
+	var prevContentCount int64
+	print := func() {
+		currContentCount := contentCount()
+		rateValueFast.Add(float64(currContentCount - prevContentCount))
+		rateValueSlow.Add(float64(currContentCount - prevContentCount))
+		prevContentCount = currContentCount
 
-func printProgress(wg *sync.WaitGroup, done <-chan struct{}, r *countingReader, name string, contentLength int64) {
-	defer wg.Done()
-	var lastBytesRead uint64
+		const vtRestartLine = "\r\x1b[K"
+		fmt.Fprintf(os.Stderr, "%s%s    %s    %s",
+			vtRestartLine,
+			rightPad(name, 36),
+			leftPad(formatIEC(float64(currContentCount), "B"), len("1023.00MiB")),
+			leftPad(formatIEC(rateValueFast.Rate(), "B/s"), len("1023.00MiB/s")))
+		if contentLength >= 0 {
+			currContentCount = min(currContentCount, contentLength) // cap at 100%
+			ratioRemain := float64(currContentCount) / float64(contentLength)
+			bytesRemain := float64(contentLength - currContentCount)
+			secsRemain := bytesRemain / rateValueSlow.Rate()
+			secs := int(min(max(0, secsRemain), 99*60*60+59+60+59))
+			fmt.Fprintf(os.Stderr, "    %s    %s",
+				leftPad(fmt.Sprintf("%0.2f%%", 100.0*ratioRemain), len("100.00%")),
+				fmt.Sprintf("ETA %02d:%02d:%02d", secs/60/60, (secs/60)%60, secs%60))
+		}
+	}
 
+	tc := time.NewTicker(250 * time.Millisecond)
+	defer tc.Stop()
+	print()
 	for {
 		select {
-		case <-done:
+		case <-ctx.Done():
+			print()
 			fmt.Fprintln(os.Stderr)
 			return
-		case <-time.After(time.Second):
-			n := r.n.Load()
-			contentLengthStr := "???"
-			if contentLength > 0 {
-				contentLengthStr = fmt.Sprint(contentLength / 1024)
-			}
-
-			fmt.Fprintf(os.Stderr, "%s%s\t\t%s", vtRestartLine, padTruncateString(name, 36), padTruncateString(fmt.Sprintf("%d/%s kb", n/1024, contentLengthStr), 16))
-			if contentLength > 0 {
-				fmt.Fprintf(os.Stderr, "\t%.02f%%", float64(n)/float64(contentLength)*100)
-			} else {
-				fmt.Fprintf(os.Stderr, "\t-------%%")
-			}
-			if lastBytesRead > 0 {
-				fmt.Fprintf(os.Stderr, "\t%d kb/s", (n-lastBytesRead)/1024)
-			} else {
-				fmt.Fprintf(os.Stderr, "\t-------")
-			}
-			lastBytesRead = n
+		case <-tc.C:
+			print()
 		}
 	}
 }
 
-func padTruncateString(str string, truncateAt int) string {
-	if len(str) <= truncateAt {
-		return str + strings.Repeat(" ", truncateAt-len(str))
-	}
+func leftPad(s string, n int) string {
+	s = truncateString(s, n)
+	return strings.Repeat(" ", max(n-len(s), 0)) + s
+}
 
-	// Truncate the string, but respect unicode codepoint boundaries.
-	// As of RFC3629 utf-8 codepoints can be at most 4 bytes wide.
-	for i := 1; i <= 4 && i < len(str)-truncateAt; i++ {
-		if utf8.ValidString(str[:truncateAt-i]) {
-			return str[:truncateAt-i] + "…"
-		}
+func rightPad(s string, n int) string {
+	s = truncateString(s, n)
+	return s + strings.Repeat(" ", max(n-len(s), 0))
+}
+
+func truncateString(s string, n int) string {
+	if len(s) <= n {
+		return s
+	}
+	return truncate.String(s, max(n-1, 0)) + "…"
+}
+
+func formatIEC(n float64, unit string) string {
+	switch {
+	case n < 1<<10:
+		return fmt.Sprintf("%0.2f%s", n/(1<<0), unit)
+	case n < 1<<20:
+		return fmt.Sprintf("%0.2fKi%s", n/(1<<10), unit)
+	case n < 1<<30:
+		return fmt.Sprintf("%0.2fMi%s", n/(1<<20), unit)
+	case n < 1<<40:
+		return fmt.Sprintf("%0.2fGi%s", n/(1<<30), unit)
+	default:
+		return fmt.Sprintf("%0.2fTi%s", n/(1<<40), unit)
 	}
-	return "" // Should be unreachable
 }
 
 func getTargetStableID(ctx context.Context, ipStr string) (id tailcfg.StableNodeID, isOffline bool, err error) {

cmd/tailscale/cli/funnel.go

@@ -13,22 +13,17 @@ import (
 	"strings"
 
 	"github.com/peterbourgon/ff/v3/ffcli"
-	"tailscale.com/envknob"
 	"tailscale.com/ipn"
-	"tailscale.com/ipn/ipnstate"
 	"tailscale.com/tailcfg"
 	"tailscale.com/util/mak"
 )
 
 var funnelCmd = func() *ffcli.Command {
 	se := &serveEnv{lc: &localClient}
-	// This flag is used to switch to an in-development
-	// implementation of the tailscale funnel command.
-	// See https://github.com/tailscale/tailscale/issues/7844
-	if envknob.UseWIPCode() {
-		return newServeDevCommand(se, funnel)
-	}
-	return newFunnelCommand(se)
+	// previously used to serve legacy newFunnelCommand unless useWIPCode is true
+	// change is limited to make a revert easier and full cleanup to come after the relase.
+	// TODO(tylersmalley): cleanup and removal of newFunnelCommand as of 2023-10-16
+	return newServeV2Command(se, funnel)
 }
 
 // newFunnelCommand returns a new "funnel" subcommand using e as its environment.
@@ -92,10 +87,6 @@ func (e *serveEnv) runFunnel(ctx context.Context, args []string) error {
 	if sc == nil {
 		sc = new(ipn.ServeConfig)
 	}
-	st, err := e.getLocalClientStatusWithoutPeers(ctx)
-	if err != nil {
-		return fmt.Errorf("getting client status: %w", err)
-	}
 
 	port64, err := strconv.ParseUint(args[0], 10, 16)
 	if err != nil {
@@ -107,11 +98,15 @@ func (e *serveEnv) runFunnel(ctx context.Context, args []string) error {
 		// Don't block from turning off existing Funnel if
 		// network configuration/capabilities have changed.
 		// Only block from starting new Funnels.
-		if err := e.verifyFunnelEnabled(ctx, st, port); err != nil {
+		if err := e.verifyFunnelEnabled(ctx, port); err != nil {
 			return err
 		}
 	}
 
+	st, err := e.getLocalClientStatusWithoutPeers(ctx)
+	if err != nil {
+		return fmt.Errorf("getting client status: %w", err)
+	}
 	dnsName := strings.TrimSuffix(st.Self.DNSName, ".")
 	hp := ipn.HostPort(dnsName + ":" + strconv.Itoa(int(port)))
 	if on == sc.AllowFunnel[hp] {
@@ -145,13 +140,7 @@ func (e *serveEnv) runFunnel(ctx context.Context, args []string) error {
 // If an error is reported, the CLI should stop execution and return the error.
 //
 // verifyFunnelEnabled may refresh the local state and modify the st input.
-func (e *serveEnv) verifyFunnelEnabled(ctx context.Context, st *ipnstate.Status, port uint16) error {
-	hasFunnelAttrs := func(selfNode *ipnstate.PeerStatus) bool {
-		return selfNode.HasCap(tailcfg.CapabilityHTTPS) && selfNode.HasCap(tailcfg.NodeAttrFunnel)
-	}
-	if hasFunnelAttrs(st.Self) {
-		return nil // already enabled
-	}
+func (e *serveEnv) verifyFunnelEnabled(ctx context.Context, port uint16) error {
 	enableErr := e.enableFeatureInteractive(ctx, "funnel", tailcfg.CapabilityHTTPS, tailcfg.NodeAttrFunnel)
 	st, statusErr := e.getLocalClientStatusWithoutPeers(ctx) // get updated status; interactive flow may block
 	switch {

cmd/tailscale/cli/serve_legacy.go

@@ -24,7 +24,6 @@ import (
 
 	"github.com/peterbourgon/ff/v3/ffcli"
 	"tailscale.com/client/tailscale"
-	"tailscale.com/envknob"
 	"tailscale.com/ipn"
 	"tailscale.com/ipn/ipnstate"
 	"tailscale.com/tailcfg"
@@ -34,17 +33,14 @@ import (
 
 var serveCmd = func() *ffcli.Command {
 	se := &serveEnv{lc: &localClient}
-	// This flag is used to switch to an in-development
-	// implementation of the tailscale funnel command.
-	// See https://github.com/tailscale/tailscale/issues/7844
-	if envknob.UseWIPCode() {
-		return newServeDevCommand(se, serve)
-	}
-	return newServeCommand(se)
+	// previously used to serve legacy newFunnelCommand unless useWIPCode is true
+	// change is limited to make a revert easier and full cleanup to come after the relase.
+	// TODO(tylersmalley): cleanup and removal of newServeLegacyCommand as of 2023-10-16
+	return newServeV2Command(se, serve)
 }
 
-// newServeCommand returns a new "serve" subcommand using e as its environment.
-func newServeCommand(e *serveEnv) *ffcli.Command {
+// newServeLegacyCommand returns a new "serve" subcommand using e as its environment.
+func newServeLegacyCommand(e *serveEnv) *ffcli.Command {
 	return &ffcli.Command{
 		Name:      "serve",
 		ShortHelp: "Serve content and local servers",
@@ -163,17 +159,19 @@ type serveEnv struct {
 	// v2 specific flags
 	bg               bool      // background mode
 	setPath          string    // serve path
-	https            string    // HTTP port
-	http             string    // HTTP port
-	tcp              string    // TCP port
-	tlsTerminatedTCP string    // a TLS terminated TCP port
+	https            uint      // HTTP port
+	http             uint      // HTTP port
+	tcp              uint      // TCP port
+	tlsTerminatedTCP uint      // a TLS terminated TCP port
 	subcmd           serveMode // subcommand
+	yes              bool      // update without prompt
 
 	lc localServeClient // localClient interface, specific to serve
 
 	// optional stuff for tests:
 	testFlagOut io.Writer
 	testStdout  io.Writer
+	testStderr  io.Writer
 }
 
 // getSelfDNSName returns the DNS name of the current node.
@@ -684,13 +682,6 @@ func (e *serveEnv) runServeStatus(ctx context.Context, args []string) error {
 	return nil
 }
 
-func (e *serveEnv) stdout() io.Writer {
-	if e.testStdout != nil {
-		return e.testStdout
-	}
-	return os.Stdout
-}
-
 func printTCPStatusTree(ctx context.Context, sc *ipn.ServeConfig, st *ipnstate.Status) error {
 	dnsName := strings.TrimSuffix(st.Self.DNSName, ".")
 	for p, h := range sc.TCP {
@@ -827,6 +818,24 @@ func parseServePort(s string) (uint16, error) {
 // 2023-08-09: The only valid feature values are "serve" and "funnel".
 // This can be moved to some CLI lib when expanded past serve/funnel.
 func (e *serveEnv) enableFeatureInteractive(ctx context.Context, feature string, caps ...tailcfg.NodeCapability) (err error) {
+	st, err := e.getLocalClientStatusWithoutPeers(ctx)
+	if err != nil {
+		return fmt.Errorf("getting client status: %w", err)
+	}
+	if st.Self == nil {
+		return errors.New("no self node")
+	}
+	hasCaps := func() bool {
+		for _, c := range caps {
+			if !st.Self.HasCap(c) {
+				return false
+			}
+		}
+		return true
+	}
+	if hasCaps() {
+		return nil // already enabled
+	}
 	info, err := e.lc.QueryFeature(ctx, feature)
 	if err != nil {
 		return err

cmd/tailscale/cli/serve_legacy_test.go

@@ -713,7 +713,7 @@ func TestServeConfigMutations(t *testing.T) {
 			cmd = newFunnelCommand(e)
 			args = st.command[1:]
 		} else {
-			cmd = newServeCommand(e)
+			cmd = newServeLegacyCommand(e)
 			args = st.command
 		}
 		err := cmd.ParseAndRun(context.Background(), args)
@@ -786,7 +786,7 @@ func TestVerifyFunnelEnabled(t *testing.T) {
 		{
 			name:                 "fallback-flow-enabled",
 			queryFeatureResponse: mockQueryFeatureResponse{resp: nil, err: errors.New("not-allowed")},
-			caps:                 []tailcfg.NodeCapability{tailcfg.CapabilityHTTPS, tailcfg.NodeAttrFunnel},
+			caps:                 []tailcfg.NodeCapability{tailcfg.CapabilityHTTPS, tailcfg.NodeAttrFunnel, "https://tailscale.com/cap/funnel-ports?ports=80,443,8080-8090"},
 			wantErr:              "", // no error, success
 		},
 		{
@@ -811,10 +811,6 @@ func TestVerifyFunnelEnabled(t *testing.T) {
 				defer func() { fakeStatus.Self.Capabilities = oldCaps }() // reset after test
 				fakeStatus.Self.Capabilities = tt.caps
 			}
-			st, err := e.getLocalClientStatusWithoutPeers(ctx)
-			if err != nil {
-				t.Fatal(err)
-			}
 
 			defer func() {
 				r := recover()
@@ -826,7 +822,7 @@ func TestVerifyFunnelEnabled(t *testing.T) {
 					t.Errorf("wrong panic; got=%s, want=%s", gotPanic, tt.wantPanic)
 				}
 			}()
-			gotErr := e.verifyFunnelEnabled(ctx, st, 443)
+			gotErr := e.verifyFunnelEnabled(ctx, 443)
 			var got string
 			if gotErr != nil {
 				got = gotErr.Error()

cmd/tailscale/cli/serve_v2.go

@@ -5,17 +5,20 @@ package cli
 
 import (
 	"context"
+	"encoding/json"
 	"errors"
 	"flag"
 	"fmt"
 	"io"
 	"log"
+	"math"
 	"net"
 	"net/url"
 	"os"
 	"os/signal"
 	"path"
 	"path/filepath"
+	"slices"
 	"sort"
 	"strconv"
 	"strings"
@@ -38,15 +41,19 @@ type commandInfo struct {
 }
 
 var serveHelpCommon = strings.TrimSpace(`
-<target> can be a port number (e.g., 3000), a partial URL (e.g., localhost:3000), or a
-full URL including a path (e.g., http://localhost:3000/foo, https+insecure://localhost:3000/foo).
+<target> can be a file, directory, text, or most commonly the location to a service running on the
+local machine. The location to the location service can be expressed as a port number (e.g., 3000),
+a partial URL (e.g., localhost:3000), or a full URL including a path (e.g., http://localhost:3000/foo).
 
 EXAMPLES
-  - Mount a local web server at 127.0.0.1:3000 in the foreground:
-    $ tailscale %s localhost:3000
+  - Expose an HTTP server running at 127.0.0.1:3000 in the foreground:
+    $ tailscale %[1]s 3000
 
-  - Mount a local web server at 127.0.0.1:3000 in the background:
-    $ tailscale %s --bg localhost:3000
+  - Expose an HTTP server running at 127.0.0.1:3000 in the background:
+    $ tailscale %[1]s --bg 3000
+
+  - Expose an HTTPS server with invalid or self-signed certificates at https://localhost:8443
+    $ tailscale %[1]s https+insecure://localhost:8443
 
 For more examples and use cases visit our docs site https://tailscale.com/kb/1247/funnel-serve-use-cases
 `)
@@ -72,7 +79,7 @@ var infoMap = map[serveMode]commandInfo{
 		Name:      "serve",
 		ShortHelp: "Serve content and local servers on your tailnet",
 		LongHelp: strings.Join([]string{
-			"Serve enables you to share a local server securely within your tailnet.\n",
+			"Tailscale Serve enables you to share a local server securely within your tailnet.\n",
 			"To share a local server on the internet, use `tailscale funnel`\n\n",
 		}, "\n"),
 	},
@@ -94,8 +101,14 @@ func buildShortUsage(subcmd string) string {
 	}, "\n  ")
 }
 
-// newServeDevCommand returns a new "serve" subcommand using e as its environment.
-func newServeDevCommand(e *serveEnv, subcmd serveMode) *ffcli.Command {
+// errHelpFunc is standard error text that prompts users to
+// run `$subcmd --help` for information on how to use serve.
+var errHelpFunc = func(m serveMode) error {
+	return fmt.Errorf("try `tailscale %s --help` for usage info", infoMap[m].Name)
+}
+
+// newServeV2Command returns a new "serve" subcommand using e as its environment.
+func newServeV2Command(e *serveEnv, subcmd serveMode) *ffcli.Command {
 	if subcmd != serve && subcmd != funnel {
 		log.Fatalf("newServeDevCommand called with unknown subcmd %q", subcmd)
 	}
@@ -110,19 +123,21 @@ func newServeDevCommand(e *serveEnv, subcmd serveMode) *ffcli.Command {
 			fmt.Sprintf("%s status [--json]", info.Name),
 			fmt.Sprintf("%s reset", info.Name),
 		}, "\n  "),
-		LongHelp: info.LongHelp + fmt.Sprintf(strings.TrimSpace(serveHelpCommon), info.Name, info.Name),
+		LongHelp: info.LongHelp + fmt.Sprintf(strings.TrimSpace(serveHelpCommon), info.Name),
 		Exec:     e.runServeCombined(subcmd),
 
 		FlagSet: e.newFlags("serve-set", func(fs *flag.FlagSet) {
-			fs.BoolVar(&e.bg, "bg", false, "run the command in the background")
-			fs.StringVar(&e.setPath, "set-path", "", "set a path for a specific target and run in the background")
-			fs.StringVar(&e.https, "https", "", "default; HTTPS listener")
-			fs.StringVar(&e.http, "http", "", "HTTP listener")
-			fs.StringVar(&e.tcp, "tcp", "", "TCP listener")
-			fs.StringVar(&e.tlsTerminatedTCP, "tls-terminated-tcp", "", "TLS terminated TCP listener")
-
+			fs.BoolVar(&e.bg, "bg", false, "Run the command as a background process (default false)")
+			fs.StringVar(&e.setPath, "set-path", "", "Appends the specified path to the base URL for accessing the underlying service")
+			fs.UintVar(&e.https, "https", 0, "Expose an HTTPS server at the specified port (default mode)")
+			if subcmd == serve {
+				fs.UintVar(&e.http, "http", 0, "Expose an HTTP server at the specified port")
+			}
+			fs.UintVar(&e.tcp, "tcp", 0, "Expose a TCP forwarder to forward raw TCP packets at the specified port")
+			fs.UintVar(&e.tlsTerminatedTCP, "tls-terminated-tcp", 0, "Expose a TCP forwarder to forward TLS-terminated TCP packets at the specified port")
+			fs.BoolVar(&e.yes, "yes", false, "Update without interactive prompts (default false)")
 		}),
-		UsageFunc: usageFunc,
+		UsageFunc: usageFuncNoDefaultValues,
 		Subcommands: []*ffcli.Command{
 			{
 				Name:      "status",
@@ -144,20 +159,31 @@ func newServeDevCommand(e *serveEnv, subcmd serveMode) *ffcli.Command {
 	}
 }
 
-func validateArgs(subcmd serveMode, args []string) error {
-	switch len(args) {
-	case 0:
-		return flag.ErrHelp
-	case 1, 2:
-		if isLegacyInvocation(subcmd, args) {
-			fmt.Fprintf(os.Stderr, "error: the CLI for serve and funnel has changed.")
-			fmt.Fprintf(os.Stderr, "Please see https://tailscale.com/kb/1242/tailscale-serve for more information.")
-			return errHelp
+func (e *serveEnv) validateArgs(subcmd serveMode, args []string) error {
+	if translation, ok := isLegacyInvocation(subcmd, args); ok {
+		fmt.Fprint(e.stderr(), "Error: the CLI for serve and funnel has changed.")
+		if translation != "" {
+			fmt.Fprint(e.stderr(), " You can run the following command instead:\n")
+			fmt.Fprintf(e.stderr(), "\t- %s\n", translation)
 		}
-	default:
-		fmt.Fprintf(os.Stderr, "error: invalid number of arguments (%d)", len(args))
-		return errHelp
+		fmt.Fprint(e.stderr(), "\nPlease see https://tailscale.com/kb/1242/tailscale-serve for more information.\n")
+		return errHelpFunc(subcmd)
 	}
+	if len(args) == 0 {
+		return flag.ErrHelp
+	}
+	if len(args) > 2 {
+		fmt.Fprintf(e.stderr(), "Error: invalid number of arguments (%d)\n", len(args))
+		return errHelpFunc(subcmd)
+	}
+	turnOff := args[len(args)-1] == "off"
+	if len(args) == 2 && !turnOff {
+		fmt.Fprintln(e.stderr(), "Error: invalid argument format")
+		return errHelpFunc(subcmd)
+	}
+
+	// Given the two checks above, we can assume there
+	// are only 1 or 2 arguments which is valid.
 	return nil
 }
 
@@ -166,22 +192,31 @@ func (e *serveEnv) runServeCombined(subcmd serveMode) execFunc {
 	e.subcmd = subcmd
 
 	return func(ctx context.Context, args []string) error {
-		if err := validateArgs(subcmd, args); err != nil {
+		// Undocumented debug command (not using ffcli subcommands) to set raw
+		// configs from stdin for now (2022-11-13).
+		if len(args) == 1 && args[0] == "set-raw" {
+			valb, err := io.ReadAll(os.Stdin)
+			if err != nil {
+				return err
+			}
+			sc := new(ipn.ServeConfig)
+			if err := json.Unmarshal(valb, sc); err != nil {
+				return fmt.Errorf("invalid JSON: %w", err)
+			}
+			return e.lc.SetServeConfig(ctx, sc)
+		}
+
+		if err := e.validateArgs(subcmd, args); err != nil {
 			return err
 		}
 
 		ctx, cancel := signal.NotifyContext(ctx, os.Interrupt)
 		defer cancel()
 
-		st, err := e.getLocalClientStatusWithoutPeers(ctx)
-		if err != nil {
-			return fmt.Errorf("getting client status: %w", err)
-		}
-
 		funnel := subcmd == funnel
 		if funnel {
 			// verify node has funnel capabilities
-			if err := e.verifyFunnelEnabled(ctx, st, 443); err != nil {
+			if err := e.verifyFunnelEnabled(ctx, 443); err != nil {
 				return err
 			}
 		}
@@ -191,18 +226,10 @@ func (e *serveEnv) runServeCombined(subcmd serveMode) execFunc {
 			return fmt.Errorf("failed to clean the mount point: %w", err)
 		}
 
-		if e.setPath != "" {
-			// TODO(marwan-at-work): either
-			// 1. Warn the user that this is a side effect.
-			// 2. Force the user to pass --bg
-			// 3. Allow set-path to be in the foreground.
-			e.bg = true
-		}
-
 		srvType, srvPort, err := srvTypeAndPortFromFlags(e)
 		if err != nil {
-			fmt.Fprintf(os.Stderr, "error: %v\n\n", err)
-			return errHelp
+			fmt.Fprintf(e.stderr(), "error: %v\n\n", err)
+			return errHelpFunc(subcmd)
 		}
 
 		sc, err := e.lc.GetServeConfig(ctx)
@@ -214,6 +241,10 @@ func (e *serveEnv) runServeCombined(subcmd serveMode) execFunc {
 		if sc == nil {
 			sc = new(ipn.ServeConfig)
 		}
+		st, err := e.getLocalClientStatusWithoutPeers(ctx)
+		if err != nil {
+			return fmt.Errorf("getting client status: %w", err)
+		}
 		dnsName := strings.TrimSuffix(st.Self.DNSName, ".")
 
 		// set parent serve config to always be persisted
@@ -239,7 +270,13 @@ func (e *serveEnv) runServeCombined(subcmd serveMode) execFunc {
 		}
 
 		var watcher *tailscale.IPNBusWatcher
-		if !e.bg && !turnOff {
+		wantFg := !e.bg && !turnOff
+		if wantFg {
+			// validate the config before creating a WatchIPNBus session
+			if err := e.validateConfig(parentSC, srvPort, srvType); err != nil {
+				return err
+			}
+
 			// if foreground mode, create a WatchIPNBus session
 			// and use the nested config for all following operations
 			// TODO(marwan-at-work): nested-config validations should happen here or previous to this point.
@@ -268,22 +305,22 @@ func (e *serveEnv) runServeCombined(subcmd serveMode) execFunc {
 				return err
 			}
 			err = e.setServe(sc, st, dnsName, srvType, srvPort, mount, args[0], funnel)
-			msg = e.messageForPort(sc, st, dnsName, srvPort)
+			msg = e.messageForPort(sc, st, dnsName, srvType, srvPort)
 		}
 		if err != nil {
-			fmt.Fprintf(os.Stderr, "error: %v\n\n", err)
-			return errHelp
+			fmt.Fprintf(e.stderr(), "error: %v\n\n", err)
+			return errHelpFunc(subcmd)
 		}
 
 		if err := e.lc.SetServeConfig(ctx, parentSC); err != nil {
 			if tailscale.IsPreconditionsFailedError(err) {
-				fmt.Fprintln(os.Stderr, "Another client is changing the serve config; please try again.")
+				fmt.Fprintln(e.stderr(), "Another client is changing the serve config; please try again.")
 			}
 			return err
 		}
 
 		if msg != "" {
-			fmt.Fprintln(os.Stderr, msg)
+			fmt.Fprintln(e.stdout(), msg)
 		}
 
 		if watcher != nil {
@@ -302,6 +339,8 @@ func (e *serveEnv) runServeCombined(subcmd serveMode) execFunc {
 	}
 }
 
+const backgroundExistsMsg = "background configuration already exists, use `tailscale %s --%s=%d off` to remove the existing configuration"
+
 func (e *serveEnv) validateConfig(sc *ipn.ServeConfig, port uint16, wantServe serveType) error {
 	sc, isFg := findConfig(sc, port)
 	if sc == nil {
@@ -311,7 +350,7 @@ func (e *serveEnv) validateConfig(sc *ipn.ServeConfig, port uint16, wantServe se
 		return errors.New("foreground already exists under this port")
 	}
 	if !e.bg {
-		return errors.New("background serve already exists under this port")
+		return fmt.Errorf(backgroundExistsMsg, infoMap[e.subcmd].Name, wantServe.String(), port)
 	}
 	existingServe := serveFromPortHandler(sc.TCP[port])
 	if wantServe != existingServe {
@@ -363,6 +402,10 @@ func (e *serveEnv) setServe(sc *ipn.ServeConfig, st *ipnstate.Status, dnsName st
 			return fmt.Errorf("failed apply web serve: %w", err)
 		}
 	case serveTypeTCP, serveTypeTLSTerminatedTCP:
+		if e.setPath != "" {
+			return fmt.Errorf("cannot mount a path for TCP serve")
+		}
+
 		err := e.applyTCPServe(sc, dnsName, srvType, srvPort, target)
 		if err != nil {
 			return fmt.Errorf("failed to apply TCP serve: %w", err)
@@ -377,18 +420,27 @@ func (e *serveEnv) setServe(sc *ipn.ServeConfig, st *ipnstate.Status, dnsName st
 	return nil
 }
 
+var (
+	msgFunnelAvailable     = "Available on the internet:"
+	msgServeAvailable      = "Available within your tailnet:"
+	msgRunningInBackground = "%s started and running in the background."
+	msgDisableProxy        = "To disable the proxy, run: tailscale %s --%s=%d off"
+	msgToExit              = "Press Ctrl+C to exit."
+)
+
 // messageForPort returns a message for the given port based on the
 // serve config and status.
-func (e *serveEnv) messageForPort(sc *ipn.ServeConfig, st *ipnstate.Status, dnsName string, srvPort uint16) string {
+func (e *serveEnv) messageForPort(sc *ipn.ServeConfig, st *ipnstate.Status, dnsName string, srvType serveType, srvPort uint16) string {
 	var output strings.Builder
 
 	hp := ipn.HostPort(net.JoinHostPort(dnsName, strconv.Itoa(int(srvPort))))
 
 	if sc.AllowFunnel[hp] == true {
-		output.WriteString("Available on the internet:\n")
+		output.WriteString(msgFunnelAvailable)
 	} else {
-		output.WriteString("Available within your tailnet:\n")
+		output.WriteString(msgServeAvailable)
 	}
+	output.WriteString("\n\n")
 
 	scheme := "https"
 	if sc.IsServingHTTP(srvPort) {
@@ -401,13 +453,6 @@ func (e *serveEnv) messageForPort(sc *ipn.ServeConfig, st *ipnstate.Status, dnsN
 		portPart = ""
 	}
 
-	output.WriteString(fmt.Sprintf("%s://%s%s\n\n", scheme, dnsName, portPart))
-
-	if !e.bg {
-		output.WriteString("Press Ctrl+C to exit.")
-		return output.String()
-	}
-
 	srvTypeAndDesc := func(h *ipn.HTTPHandler) (string, string) {
 		switch {
 		case h.Path != "":
@@ -429,12 +474,12 @@ func (e *serveEnv) messageForPort(sc *ipn.ServeConfig, st *ipnstate.Status, dnsN
 		sort.Slice(mounts, func(i, j int) bool {
 			return len(mounts[i]) < len(mounts[j])
 		})
-		maxLen := len(mounts[len(mounts)-1])
 
 		for _, m := range mounts {
 			h := sc.Web[hp].Handlers[m]
 			t, d := srvTypeAndDesc(h)
-			output.WriteString(fmt.Sprintf("%s %s%s %-5s %s\n", "|--", m, strings.Repeat(" ", maxLen-len(m)), t, d))
+			output.WriteString(fmt.Sprintf("%s://%s%s%s\n", scheme, dnsName, portPart, m))
+			output.WriteString(fmt.Sprintf("%s %-5s %s\n\n", "|--", t, d))
 		}
 	} else if sc.TCP[srvPort] != nil {
 		h := sc.TCP[srvPort]
@@ -444,6 +489,7 @@ func (e *serveEnv) messageForPort(sc *ipn.ServeConfig, st *ipnstate.Status, dnsN
 			tlsStatus = "TLS terminated"
 		}
 
+		output.WriteString(fmt.Sprintf("%s://%s%s\n", scheme, dnsName, portPart))
 		output.WriteString(fmt.Sprintf("|-- tcp://%s (%s)\n", hp, tlsStatus))
 		for _, a := range st.TailscaleIPs {
 			ipp := net.JoinHostPort(a.String(), strconv.Itoa(int(srvPort)))
@@ -452,8 +498,17 @@ func (e *serveEnv) messageForPort(sc *ipn.ServeConfig, st *ipnstate.Status, dnsN
 		output.WriteString(fmt.Sprintf("|--> tcp://%s\n", h.TCPForward))
 	}
 
-	output.WriteString("\nServe started and running in the background.\n")
-	output.WriteString(fmt.Sprintf("To disable the proxy, run: tailscale %s off", infoMap[e.subcmd].Name))
+	if !e.bg {
+		output.WriteString(msgToExit)
+		return output.String()
+	}
+
+	subCmd := infoMap[e.subcmd].Name
+	subCmdUpper := strings.ToUpper(string(subCmd[0])) + subCmd[1:]
+
+	output.WriteString(fmt.Sprintf(msgRunningInBackground, subCmdUpper))
+	output.WriteString("\n")
+	output.WriteString(fmt.Sprintf(msgDisableProxy, subCmd, srvType.String(), srvPort))
 
 	return output.String()
 }
@@ -488,7 +543,7 @@ func (e *serveEnv) applyWebServe(sc *ipn.ServeConfig, dnsName string, srvPort ui
 		}
 		h.Path = target
 	default:
-		t, err := expandProxyTargetDev(target)
+		t, err := expandProxyTargetDev(target, []string{"http", "https", "https+insecure"}, "http")
 		if err != nil {
 			return err
 		}
@@ -538,34 +593,22 @@ func (e *serveEnv) applyTCPServe(sc *ipn.ServeConfig, dnsName string, srcType se
 		return fmt.Errorf("invalid TCP target %q", target)
 	}
 
-	dstURL, err := url.Parse(target)
+	targetURL, err := expandProxyTargetDev(target, []string{"tcp"}, "tcp")
+	if err != nil {
+		return fmt.Errorf("unable to expand target: %v", err)
+	}
+
+	dstURL, err := url.Parse(targetURL)
 	if err != nil {
 		return fmt.Errorf("invalid TCP target %q: %v", target, err)
 	}
-	host, dstPortStr, err := net.SplitHostPort(dstURL.Host)
-	if err != nil {
-		return fmt.Errorf("invalid TCP target %q: %v", target, err)
-	}
-
-	switch host {
-	case "localhost", "127.0.0.1":
-		// ok
-	default:
-		return fmt.Errorf("invalid TCP target %q, must be one of localhost or 127.0.0.1", target)
-	}
-
-	if p, err := strconv.ParseUint(dstPortStr, 10, 16); p == 0 || err != nil {
-		return fmt.Errorf("invalid port %q", dstPortStr)
-	}
-
-	fwdAddr := "127.0.0.1:" + dstPortStr
 
 	// TODO: needs to account for multiple configs from foreground mode
 	if sc.IsServingWeb(srcPort) {
 		return fmt.Errorf("cannot serve TCP; already serving web on %d", srcPort)
 	}
 
-	mak.Set(&sc.TCP, srcPort, &ipn.TCPPortHandler{TCPForward: fwdAddr})
+	mak.Set(&sc.TCP, srcPort, &ipn.TCPPortHandler{TCPForward: dstURL.Host})
 
 	if terminateTLS {
 		sc.TCP[srcPort].TerminateTLS = dnsName
@@ -587,6 +630,9 @@ func (e *serveEnv) applyFunnel(sc *ipn.ServeConfig, dnsName string, srvPort uint
 	// TODO: add error handling for if toggling for existing sc
 	if allowFunnel {
 		mak.Set(&sc.AllowFunnel, hp, true)
+	} else if _, exists := sc.AllowFunnel[hp]; exists {
+		fmt.Fprintf(e.stderr(), "Removing Funnel for %s\n", hp)
+		delete(sc.AllowFunnel, hp)
 	}
 }
 
@@ -613,7 +659,7 @@ func (e *serveEnv) unsetServe(sc *ipn.ServeConfig, dnsName string, srvType serve
 }
 
 func srvTypeAndPortFromFlags(e *serveEnv) (srvType serveType, srvPort uint16, err error) {
-	sourceMap := map[serveType]string{
+	sourceMap := map[serveType]uint{
 		serveTypeHTTP:             e.http,
 		serveTypeHTTPS:            e.https,
 		serveTypeTCP:              e.tcp,
@@ -621,13 +667,15 @@ func srvTypeAndPortFromFlags(e *serveEnv) (srvType serveType, srvPort uint16, er
 	}
 
 	var srcTypeCount int
-	var srcValue string
 
 	for k, v := range sourceMap {
-		if v != "" {
+		if v != 0 {
+			if v > math.MaxUint16 {
+				return 0, 0, fmt.Errorf("port number %d is too high for %s flag", v, srvType)
+			}
 			srcTypeCount++
 			srvType = k
-			srcValue = v
+			srvPort = uint16(v)
 		}
 	}
 
@@ -635,29 +683,104 @@ func srvTypeAndPortFromFlags(e *serveEnv) (srvType serveType, srvPort uint16, er
 		return 0, 0, fmt.Errorf("cannot serve multiple types for a single mount point")
 	} else if srcTypeCount == 0 {
 		srvType = serveTypeHTTPS
-		srcValue = "443"
-	}
-
-	srvPort, err = parseServePort(srcValue)
-	if err != nil {
-		return 0, 0, fmt.Errorf("invalid port %q: %w", srcValue, err)
+		srvPort = 443
 	}
 
 	return srvType, srvPort, nil
 }
 
-func isLegacyInvocation(subcmd serveMode, args []string) bool {
-	if subcmd == serve && len(args) == 2 {
-		prefixes := []string{"http", "https", "tcp", "tls-terminated-tcp"}
+// isLegacyInvocation helps transition customers who have been using the beta
+// CLI to the newer API by returning a translation from the old command to the new command.
+// The second result is a boolean that only returns true if the given arguments is a valid
+// legacy invocation. If the given args are in the old format but are not valid, it will
+// return false and expects the new code path has enough validations to reject the request.
+func isLegacyInvocation(subcmd serveMode, args []string) (string, bool) {
+	if subcmd == funnel {
+		if len(args) != 2 {
+			return "", false
+		}
+		_, err := strconv.ParseUint(args[0], 10, 16)
+		return "", err == nil && (args[1] == "on" || args[1] == "off")
+	}
+	turnOff := len(args) > 1 && args[len(args)-1] == "off"
+	if turnOff {
+		args = args[:len(args)-1]
+	}
+	if len(args) == 0 {
+		return "", false
+	}
 
-		for _, prefix := range prefixes {
-			if strings.HasPrefix(args[0], prefix) {
-				return true
-			}
+	srcType, srcPortStr, found := strings.Cut(args[0], ":")
+	if !found {
+		if srcType == "https" && srcPortStr == "" {
+			// Default https port to 443.
+			srcPortStr = "443"
+		} else if srcType == "http" && srcPortStr == "" {
+			// Default http port to 80.
+			srcPortStr = "80"
+		} else {
+			return "", false
 		}
 	}
 
-	return false
+	var wantLength int
+	switch srcType {
+	case "https", "http":
+		wantLength = 3
+	case "tcp", "tls-terminated-tcp":
+		wantLength = 2
+	default:
+		// return non-legacy, and let new code handle validation.
+		return "", false
+	}
+	// The length is either exactlly the same as in "https / <target>"
+	// or target is omitted as in "https / off" where omit the off at
+	// the top.
+	if len(args) != wantLength && !(turnOff && len(args) == wantLength-1) {
+		return "", false
+	}
+
+	cmd := []string{"tailscale", "serve", "--bg"}
+	switch srcType {
+	case "https":
+		// In the new code, we default to https:443,
+		// so we don't need to pass the flag explicitly.
+		if srcPortStr != "443" {
+			cmd = append(cmd, fmt.Sprintf("--https %s", srcPortStr))
+		}
+	case "http":
+		cmd = append(cmd, fmt.Sprintf("--http %s", srcPortStr))
+	case "tcp", "tls-terminated-tcp":
+		cmd = append(cmd, fmt.Sprintf("--%s %s", srcType, srcPortStr))
+	}
+
+	var mount string
+	if srcType == "https" || srcType == "http" {
+		mount = args[1]
+		if _, err := cleanMountPoint(mount); err != nil {
+			return "", false
+		}
+		if mount != "/" {
+			cmd = append(cmd, "--set-path "+mount)
+		}
+	}
+
+	// If there's no "off" there must always be a target destination.
+	// If there is "off", target is optional so check if it exists
+	// first before appending it.
+	hasTarget := !turnOff || (turnOff && len(args) == wantLength)
+	if hasTarget {
+		dest := args[len(args)-1]
+		if strings.Contains(dest, " ") {
+			dest = strconv.Quote(dest)
+		}
+		cmd = append(cmd, dest)
+	}
+	if turnOff {
+		cmd = append(cmd, "off")
+	}
+
+	return strings.Join(cmd, " "), true
 }
 
 // removeWebServe removes a web handler from the serve config
@@ -669,15 +792,43 @@ func (e *serveEnv) removeWebServe(sc *ipn.ServeConfig, dnsName string, srvPort u
 		return errors.New("cannot remove web handler; currently serving TCP")
 	}
 
-	hp := ipn.HostPort(net.JoinHostPort(dnsName, strconv.Itoa(int(srvPort))))
-	if !sc.WebHandlerExists(hp, mount) {
+	portStr := strconv.Itoa(int(srvPort))
+	hp := ipn.HostPort(net.JoinHostPort(dnsName, portStr))
+
+	var targetExists bool
+	var mounts []string
+	// mount is deduced from e.setPath but it is ambiguous as
+	// to whether the user explicitly passed "/" or it was defaulted to.
+	if e.setPath == "" {
+		targetExists = sc.Web[hp] != nil && len(sc.Web[hp].Handlers) > 0
+		if targetExists {
+			for mount := range sc.Web[hp].Handlers {
+				mounts = append(mounts, mount)
+			}
+		}
+	} else {
+		targetExists = sc.WebHandlerExists(hp, mount)
+		mounts = []string{mount}
+	}
+
+	if !targetExists {
 		return errors.New("error: handler does not exist")
 	}
 
+	if len(mounts) > 1 {
+		msg := fmt.Sprintf("Are you sure you want to delete %d handlers under port %s?", len(mounts), portStr)
+		if !e.yes && !promptYesNo(msg) {
+			return nil
+		}
+	}
+
 	// delete existing handler, then cascade delete if empty
-	delete(sc.Web[hp].Handlers, mount)
+	for _, m := range mounts {
+		delete(sc.Web[hp].Handlers, m)
+	}
 	if len(sc.Web[hp].Handlers) == 0 {
 		delete(sc.Web, hp)
+		delete(sc.AllowFunnel, hp)
 		delete(sc.TCP, srvPort)
 	}
 
@@ -695,6 +846,10 @@ func (e *serveEnv) removeWebServe(sc *ipn.ServeConfig, dnsName string, srvPort u
 		delete(sc.AllowFunnel, hp)
 	}
 
+	if len(sc.AllowFunnel) == 0 {
+		sc.AllowFunnel = nil
+	}
+
 	return nil
 }
 
@@ -725,24 +880,22 @@ func (e *serveEnv) removeTCPServe(sc *ipn.ServeConfig, src uint16) error {
 // examples:
 //   - 3000
 //   - localhost:3000
+//   - tcp://localhost:3000
 //   - http://localhost:3000
 //   - https://localhost:3000
 //   - https-insecure://localhost:3000
 //   - https-insecure://localhost:3000/foo
-func expandProxyTargetDev(target string) (string, error) {
-	var (
-		scheme = "http"
-		host   = "127.0.0.1"
-	)
+func expandProxyTargetDev(target string, supportedSchemes []string, defaultScheme string) (string, error) {
+	const host = "127.0.0.1"
 
 	// support target being a port number
 	if port, err := strconv.ParseUint(target, 10, 16); err == nil {
-		return fmt.Sprintf("%s://%s:%d", scheme, host, port), nil
+		return fmt.Sprintf("%s://%s:%d", defaultScheme, host, port), nil
 	}
 
 	// prepend scheme if not present
 	if !strings.Contains(target, "://") {
-		target = scheme + "://" + target
+		target = defaultScheme + "://" + target
 	}
 
 	// make sure we can parse the target
@@ -752,10 +905,15 @@ func expandProxyTargetDev(target string) (string, error) {
 	}
 
 	// ensure a supported scheme
-	switch u.Scheme {
-	case "http", "https", "https+insecure":
+	if !slices.Contains(supportedSchemes, u.Scheme) {
+		return "", fmt.Errorf("must be a URL starting with one of the supported schemes: %v", supportedSchemes)
+	}
+
+	// validate the host.
+	switch u.Hostname() {
+	case "localhost", "127.0.0.1":
 	default:
-		return "", errors.New("must be a URL starting with http://, https://, or https+insecure://")
+		return "", errors.New("only localhost or 127.0.0.1 proxies are currently supported")
 	}
 
 	// validate the port
@@ -764,13 +922,7 @@ func expandProxyTargetDev(target string) (string, error) {
 		return "", fmt.Errorf("invalid port %q", u.Port())
 	}
 
-	// validate the host.
-	switch u.Hostname() {
-	case "localhost", "127.0.0.1":
-		u.Host = fmt.Sprintf("%s:%d", host, port)
-	default:
-		return "", errors.New("only localhost or 127.0.0.1 proxies are currently supported")
-	}
+	u.Host = fmt.Sprintf("%s:%d", host, port)
 
 	return u.String(), nil
 }
@@ -808,3 +960,17 @@ func (s serveType) String() string {
 		return "unknownServeType"
 	}
 }
+
+func (e *serveEnv) stdout() io.Writer {
+	if e.testStdout != nil {
+		return e.testStdout
+	}
+	return os.Stdout
+}
+
+func (e *serveEnv) stderr() io.Writer {
+	if e.testStderr != nil {
+		return e.testStderr
+	}
+	return os.Stderr
+}

cmd/tailscale/cli/set.go

@@ -9,6 +9,7 @@ import (
 	"flag"
 	"fmt"
 	"net/netip"
+	"os/exec"
 
 	"github.com/peterbourgon/ff/v3/ffcli"
 	"tailscale.com/clientupdate"
@@ -17,6 +18,7 @@ import (
 	"tailscale.com/net/tsaddr"
 	"tailscale.com/safesocket"
 	"tailscale.com/types/views"
+	"tailscale.com/version"
 )
 
 var setCmd = &ffcli.Command{
@@ -43,12 +45,14 @@ type setArgsT struct {
 	hostname               string
 	advertiseRoutes        string
 	advertiseDefaultRoute  bool
+	advertiseConnector     bool
 	opUser                 string
 	acceptedRisks          string
 	profileName            string
 	forceDaemon            bool
 	updateCheck            bool
 	updateApply            bool
+	postureChecking        bool
 }
 
 func newSetFlagSet(goos string, setArgs *setArgsT) *flag.FlagSet {
@@ -64,8 +68,11 @@ func newSetFlagSet(goos string, setArgs *setArgsT) *flag.FlagSet {
 	setf.StringVar(&setArgs.hostname, "hostname", "", "hostname to use instead of the one provided by the OS")
 	setf.StringVar(&setArgs.advertiseRoutes, "advertise-routes", "", "routes to advertise to other nodes (comma-separated, e.g. \"10.0.0.0/8,192.168.0.0/24\") or empty string to not advertise routes")
 	setf.BoolVar(&setArgs.advertiseDefaultRoute, "advertise-exit-node", false, "offer to be an exit node for internet traffic for the tailnet")
-	setf.BoolVar(&setArgs.updateCheck, "update-check", true, "HIDDEN: notify about available Tailscale updates")
-	setf.BoolVar(&setArgs.updateApply, "auto-update", false, "HIDDEN: automatically update to the latest available version")
+	setf.BoolVar(&setArgs.advertiseConnector, "advertise-connector", false, "offer to be an exit node for internet traffic for the tailnet")
+	setf.BoolVar(&setArgs.updateCheck, "update-check", true, "notify about available Tailscale updates")
+	setf.BoolVar(&setArgs.updateApply, "auto-update", false, "automatically update to the latest available version")
+	setf.BoolVar(&setArgs.postureChecking, "posture-checking", false, "HIDDEN: allow management plane to gather device posture information")
+
 	if safesocket.GOOSUsesPeerCreds(goos) {
 		setf.StringVar(&setArgs.opUser, "operator", "", "Unix username to allow to operate on tailscaled without sudo")
 	}
@@ -108,6 +115,10 @@ func runSet(ctx context.Context, args []string) (retErr error) {
 				Check: setArgs.updateCheck,
 				Apply: setArgs.updateApply,
 			},
+			AppConnector: ipn.AppConnectorPrefs{
+				Advertise: setArgs.advertiseConnector,
+			},
+			PostureChecking: setArgs.postureChecking,
 		},
 	}
 
@@ -153,9 +164,22 @@ func runSet(ctx context.Context, args []string) (retErr error) {
 		}
 	}
 	if maskedPrefs.AutoUpdateSet {
-		_, err := clientupdate.NewUpdater(clientupdate.Arguments{})
-		if errors.Is(err, errors.ErrUnsupported) {
-			return errors.New("automatic updates are not supported on this platform")
+		// On macsys, tailscaled will set the Sparkle auto-update setting. It
+		// does not use clientupdate.
+		if version.IsMacSysExt() {
+			apply := "0"
+			if maskedPrefs.AutoUpdate.Apply {
+				apply = "1"
+			}
+			out, err := exec.Command("defaults", "write", "io.tailscale.ipn.macsys", "SUAutomaticallyUpdate", apply).CombinedOutput()
+			if err != nil {
+				return fmt.Errorf("failed to enable automatic updates: %v, %q", err, out)
+			}
+		} else {
+			_, err := clientupdate.NewUpdater(clientupdate.Arguments{ForAutoUpdate: true})
+			if errors.Is(err, errors.ErrUnsupported) {
+				return errors.New("automatic updates are not supported on this platform")
+			}
 		}
 	}
 	checkPrefs := curPrefs.Clone()

cmd/tailscale/cli/status.go

@@ -238,7 +238,11 @@ func runStatus(ctx context.Context, args []string) error {
 	}
 	printFunnelStatus(ctx)
 	if cv := st.ClientVersion; cv != nil && !cv.RunningLatest && cv.LatestVersion != "" {
-		printf("# Update available: %v -> %v, run `tailscale update` or `tailscale set --auto-update` to update.\n", version.Short(), cv.LatestVersion)
+		if cv.UrgentSecurityUpdate {
+			printf("# Security update available: %v -> %v, run `tailscale update` or `tailscale set --auto-update` to update.\n", version.Short(), cv.LatestVersion)
+		} else {
+			printf("# Update available: %v -> %v, run `tailscale update` or `tailscale set --auto-update` to update.\n", version.Short(), cv.LatestVersion)
+		}
 	}
 	return nil
 }

cmd/tailscale/cli/up.go

@@ -113,7 +113,9 @@ func newUpFlagSet(goos string, upArgs *upArgsT, cmd string) *flag.FlagSet {
 	upf.StringVar(&upArgs.advertiseTags, "advertise-tags", "", "comma-separated ACL tags to request; each must start with \"tag:\" (e.g. \"tag:eng,tag:montreal,tag:ssh\")")
 	upf.StringVar(&upArgs.hostname, "hostname", "", "hostname to use instead of the one provided by the OS")
 	upf.StringVar(&upArgs.advertiseRoutes, "advertise-routes", "", "routes to advertise to other nodes (comma-separated, e.g. \"10.0.0.0/8,192.168.0.0/24\") or empty string to not advertise routes")
+	upf.BoolVar(&upArgs.advertiseConnector, "advertise-connector", false, "advertise this node as an app connector")
 	upf.BoolVar(&upArgs.advertiseDefaultRoute, "advertise-exit-node", false, "offer to be an exit node for internet traffic for the tailnet")
+
 	if safesocket.GOOSUsesPeerCreds(goos) {
 		upf.StringVar(&upArgs.opUser, "operator", "", "Unix username to allow to operate on tailscaled without sudo")
 	}
@@ -164,6 +166,7 @@ type upArgsT struct {
 	advertiseRoutes        string
 	advertiseDefaultRoute  bool
 	advertiseTags          string
+	advertiseConnector     bool
 	snat                   bool
 	netfilterMode          string
 	authKeyOrFile          string // "secret" or "file:/path/to/secret"
@@ -282,6 +285,7 @@ func prefsFromUpArgs(upArgs upArgsT, warnf logger.Logf, st *ipnstate.Status, goo
 	prefs.ForceDaemon = upArgs.forceDaemon
 	prefs.OperatorUser = upArgs.opUser
 	prefs.ProfileName = upArgs.profileName
+	prefs.AppConnector.Advertise = upArgs.advertiseConnector
 
 	if goos == "linux" {
 		prefs.NoSNAT = !upArgs.snat
@@ -532,7 +536,11 @@ func runUp(ctx context.Context, cmd string, args []string, upArgs upArgsT) (retE
 						// Only need to print an update if we printed the "please click" message earlier.
 						fmt.Fprintf(Stderr, "Success.\n")
 						if cv != nil && !cv.RunningLatest && cv.LatestVersion != "" {
-							fmt.Fprintf(Stderr, "\nUpdate available: %v -> %v\n", version.Short(), cv.LatestVersion)
+							if cv.UrgentSecurityUpdate {
+								fmt.Fprintf(Stderr, "\nSecurity update available: %v -> %v\n", version.Short(), cv.LatestVersion)
+							} else {
+								fmt.Fprintf(Stderr, "\nUpdate available: %v -> %v\n", version.Short(), cv.LatestVersion)
+							}
 							fmt.Fprintln(Stderr, "Changelog: https://tailscale.com/changelog/#client")
 							fmt.Fprintln(Stderr, "Run `tailscale update` or `tailscale set --auto-update` to update")
 						}
@@ -725,6 +733,8 @@ func init() {
 	addPrefFlagMapping("nickname", "ProfileName")
 	addPrefFlagMapping("update-check", "AutoUpdate")
 	addPrefFlagMapping("auto-update", "AutoUpdate")
+	addPrefFlagMapping("advertise-connector", "AppConnector")
+	addPrefFlagMapping("posture-checking", "PostureChecking")
 }
 
 func addPrefFlagMapping(flagName string, prefNames ...string) {
@@ -959,6 +969,8 @@ func prefsToFlags(env upCheckEnv, prefs *ipn.Prefs) (flagVal map[string]any) {
 			set(sb.String())
 		case "advertise-exit-node":
 			set(hasExitNodeRoutes(prefs.AdvertiseRoutes))
+		case "advertise-connector":
+			set(prefs.AppConnector.Advertise)
 		case "snat-subnet-routes":
 			set(!prefs.NoSNAT)
 		case "netfilter-mode":

cmd/tailscale/cli/update.go

@@ -20,13 +20,12 @@ import (
 var updateCmd = &ffcli.Command{
 	Name:       "update",
 	ShortUsage: "update",
-	ShortHelp:  "[ALPHA] Update Tailscale to the latest/different version",
+	ShortHelp:  "[BETA] Update Tailscale to the latest/different version",
 	Exec:       runUpdate,
 	FlagSet: (func() *flag.FlagSet {
 		fs := newFlagSet("update")
 		fs.BoolVar(&updateArgs.yes, "yes", false, "update without interactive prompts")
 		fs.BoolVar(&updateArgs.dryRun, "dry-run", false, "print what update would do without doing it, or prompts")
-		fs.BoolVar(&updateArgs.appStore, "app-store", false, "HIDDEN: check the App Store for updates, even if this is not an App Store install (for testing only)")
 		// These flags are not supported on several systems that only provide
 		// the latest version of Tailscale:
 		//
@@ -42,11 +41,10 @@ var updateCmd = &ffcli.Command{
 }
 
 var updateArgs struct {
-	yes      bool
-	dryRun   bool
-	appStore bool
-	track    string // explicit track; empty means same as current
-	version  string // explicit version; empty means auto
+	yes     bool
+	dryRun  bool
+	track   string // explicit track; empty means same as current
+	version string // explicit version; empty means auto
 }
 
 func runUpdate(ctx context.Context, args []string) error {
@@ -61,10 +59,11 @@ func runUpdate(ctx context.Context, args []string) error {
 		ver = updateArgs.track
 	}
 	err := clientupdate.Update(clientupdate.Arguments{
-		Version:  ver,
-		AppStore: updateArgs.appStore,
-		Logf:     func(format string, args ...any) { fmt.Printf(format+"\n", args...) },
-		Confirm:  confirmUpdate,
+		Version: ver,
+		Logf:    func(f string, a ...any) { printf(f+"\n", a...) },
+		Stdout:  Stdout,
+		Stderr:  Stderr,
+		Confirm: confirmUpdate,
 	})
 	if errors.Is(err, errors.ErrUnsupported) {
 		return errors.New("The 'update' command is not supported on this platform; see https://tailscale.com/s/client-updates")
@@ -83,7 +82,14 @@ func confirmUpdate(ver string) bool {
 		return false
 	}
 
-	fmt.Printf("This will update Tailscale from %v to %v. Continue? [y/n] ", version.Short(), ver)
+	msg := fmt.Sprintf("This will update Tailscale from %v to %v. Continue?", version.Short(), ver)
+	return promptYesNo(msg)
+}
+
+// PromptYesNo takes a question and prompts the user to answer the
+// question with a yes or no. It appends a [y/n] to the message.
+func promptYesNo(msg string) bool {
+	fmt.Print(msg + " [y/n] ")
 	var resp string
 	fmt.Scanln(&resp)
 	resp = strings.ToLower(resp)

cmd/tailscale/cli/web.go

@@ -14,10 +14,13 @@ import (
 	"net/http"
 	"net/http/cgi"
 	"os"
+	"os/signal"
 	"strings"
 
 	"github.com/peterbourgon/ff/v3/ffcli"
 	"tailscale.com/client/web"
+	"tailscale.com/ipn"
+	"tailscale.com/tailcfg"
 	"tailscale.com/util/cmpx"
 )
 
@@ -38,7 +41,6 @@ Tailscale, as opposed to a CLI or a native app.
 		webf := newFlagSet("web")
 		webf.StringVar(&webArgs.listen, "listen", "localhost:8088", "listen address; use port 0 for automatic")
 		webf.BoolVar(&webArgs.cgi, "cgi", false, "run as CGI script")
-		webf.BoolVar(&webArgs.dev, "dev", false, "run web client in developer mode [this flag is in development, use is unsupported]")
 		webf.StringVar(&webArgs.prefix, "prefix", "", "URL prefix added to requests (for cgi or reverse proxies)")
 		return webf
 	})(),
@@ -48,7 +50,6 @@ Tailscale, as opposed to a CLI or a native app.
 var webArgs struct {
 	listen string
 	cgi    bool
-	dev    bool
 	prefix string
 }
 
@@ -76,34 +77,74 @@ func tlsConfigFromEnvironment() *tls.Config {
 }
 
 func runWeb(ctx context.Context, args []string) error {
+	ctx, cancel := signal.NotifyContext(ctx, os.Interrupt)
+	defer cancel()
+
 	if len(args) > 0 {
 		return fmt.Errorf("too many non-flag arguments: %q", args)
 	}
 
-	webServer, cleanup := web.NewServer(ctx, web.ServerOpts{
-		DevMode:     webArgs.dev,
+	st, err := localClient.StatusWithoutPeers(ctx)
+	if err != nil {
+		return fmt.Errorf("getting client status: %w", err)
+	}
+	hasPreviewCap := st.Self.HasCap(tailcfg.CapabilityPreviewWebClient)
+
+	cliServerMode := web.LegacyServerMode
+	var existingWebClient bool
+	if prefs, err := localClient.GetPrefs(ctx); err == nil {
+		existingWebClient = prefs.RunWebClient
+	}
+	if hasPreviewCap {
+		cliServerMode = web.LoginServerMode
+		if !existingWebClient {
+			// Also start full client in tailscaled.
+			log.Printf("starting tailscaled web client at %s:5252\n", st.Self.TailscaleIPs[0])
+			if err := setRunWebClient(ctx, true); err != nil {
+				return fmt.Errorf("starting web client in tailscaled: %w", err)
+			}
+		}
+	}
+
+	webServer, err := web.NewServer(web.ServerOpts{
+		Mode:        cliServerMode,
 		CGIMode:     webArgs.cgi,
 		PathPrefix:  webArgs.prefix,
 		LocalClient: &localClient,
 	})
-	defer cleanup()
+	if err != nil {
+		log.Printf("tailscale.web: %v", err)
+		return err
+	}
+	go func() {
+		select {
+		case <-ctx.Done():
+			// Shutdown the server.
+			webServer.Shutdown()
+			if hasPreviewCap && !webArgs.cgi && !existingWebClient {
+				log.Println("stopping tailscaled web client")
+				// When not in cgi mode, shut down the tailscaled
+				// web client on cli termination.
+				if err := setRunWebClient(context.Background(), false); err != nil {
+					log.Printf("stopping tailscaled web client: %v", err)
+				}
+			}
+		}
+		os.Exit(0)
+	}()
 
 	if webArgs.cgi {
 		if err := cgi.Serve(webServer); err != nil {
 			log.Printf("tailscale.cgi: %v", err)
-			return err
 		}
 		return nil
-	}
-
-	tlsConfig := tlsConfigFromEnvironment()
-	if tlsConfig != nil {
+	} else if tlsConfig := tlsConfigFromEnvironment(); tlsConfig != nil {
 		server := &http.Server{
 			Addr:      webArgs.listen,
 			TLSConfig: tlsConfig,
 			Handler:   webServer,
 		}
-
+		defer server.Shutdown(ctx)
 		log.Printf("web server running on: https://%s", server.Addr)
 		return server.ListenAndServeTLS("", "")
 	} else {
@@ -112,6 +153,14 @@ func runWeb(ctx context.Context, args []string) error {
 	}
 }
 
+func setRunWebClient(ctx context.Context, val bool) error {
+	_, err := localClient.EditPrefs(ctx, &ipn.MaskedPrefs{
+		Prefs:           ipn.Prefs{RunWebClient: val},
+		RunWebClientSet: true,
+	})
+	return err
+}
+
 // urlOfListenAddr parses a given listen address into a formatted URL
 func urlOfListenAddr(addr string) string {
 	host, port, _ := net.SplitHostPort(addr)

cmd/tailscale/depaware.txt

@@ -2,11 +2,6 @@ tailscale.com/cmd/tailscale dependencies: (generated by github.com/tailscale/dep
 
         filippo.io/edwards25519                                      from github.com/hdevalence/ed25519consensus
         filippo.io/edwards25519/field                                from filippo.io/edwards25519
-   W 💣 github.com/Microsoft/go-winio                                from tailscale.com/safesocket
-   W 💣 github.com/Microsoft/go-winio/internal/fs                    from github.com/Microsoft/go-winio
-   W 💣 github.com/Microsoft/go-winio/internal/socket                from github.com/Microsoft/go-winio
-   W    github.com/Microsoft/go-winio/internal/stringbuffer          from github.com/Microsoft/go-winio/internal/fs
-   W    github.com/Microsoft/go-winio/pkg/guid                       from github.com/Microsoft/go-winio+
    W 💣 github.com/alexbrainman/sspi                                 from github.com/alexbrainman/sspi/negotiate+
    W    github.com/alexbrainman/sspi/internal/common                 from github.com/alexbrainman/sspi/negotiate
    W 💣 github.com/alexbrainman/sspi/negotiate                       from tailscale.com/net/tshttpproxy
@@ -17,7 +12,6 @@ tailscale.com/cmd/tailscale dependencies: (generated by github.com/tailscale/dep
         github.com/fxamacker/cbor/v2                                 from tailscale.com/tka
    L 💣 github.com/godbus/dbus/v5                                    from github.com/coreos/go-systemd/v22/dbus
         github.com/golang/groupcache/lru                             from tailscale.com/net/dnscache
-        github.com/google/btree                                      from gvisor.dev/gvisor/pkg/tcpip/header
    L    github.com/google/nftables                                   from tailscale.com/util/linuxfw
    L 💣 github.com/google/nftables/alignedbuff                       from github.com/google/nftables/xt
    L 💣 github.com/google/nftables/binaryutil                        from github.com/google/nftables+
@@ -48,6 +42,11 @@ tailscale.com/cmd/tailscale dependencies: (generated by github.com/tailscale/dep
         github.com/skip2/go-qrcode                                   from tailscale.com/cmd/tailscale/cli
         github.com/skip2/go-qrcode/bitset                            from github.com/skip2/go-qrcode+
         github.com/skip2/go-qrcode/reedsolomon                       from github.com/skip2/go-qrcode
+   W 💣 github.com/tailscale/go-winio                                from tailscale.com/safesocket
+   W 💣 github.com/tailscale/go-winio/internal/fs                    from github.com/tailscale/go-winio
+   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/goupnp                                  from github.com/tailscale/goupnp/dcps/internetgateway2+
         github.com/tailscale/goupnp/dcps/internetgateway2            from tailscale.com/net/portmapper
         github.com/tailscale/goupnp/httpu                            from github.com/tailscale/goupnp+
@@ -65,22 +64,6 @@ tailscale.com/cmd/tailscale dependencies: (generated by github.com/tailscale/dep
         go4.org/netipx                                               from tailscale.com/wgengine/filter+
    W 💣 golang.zx2c4.com/wireguard/windows/tunnel/winipcfg           from tailscale.com/net/interfaces+
         gopkg.in/yaml.v2                                             from sigs.k8s.io/yaml
-        gvisor.dev/gvisor/pkg/atomicbitops                           from gvisor.dev/gvisor/pkg/buffer+
-        gvisor.dev/gvisor/pkg/bits                                   from gvisor.dev/gvisor/pkg/buffer
-     💣 gvisor.dev/gvisor/pkg/buffer                                 from gvisor.dev/gvisor/pkg/tcpip+
-        gvisor.dev/gvisor/pkg/context                                from gvisor.dev/gvisor/pkg/refs
-     💣 gvisor.dev/gvisor/pkg/gohacks                                from gvisor.dev/gvisor/pkg/state/wire+
-        gvisor.dev/gvisor/pkg/linewriter                             from gvisor.dev/gvisor/pkg/log
-        gvisor.dev/gvisor/pkg/log                                    from gvisor.dev/gvisor/pkg/context+
-        gvisor.dev/gvisor/pkg/refs                                   from gvisor.dev/gvisor/pkg/buffer
-     💣 gvisor.dev/gvisor/pkg/state                                  from gvisor.dev/gvisor/pkg/atomicbitops+
-        gvisor.dev/gvisor/pkg/state/wire                             from gvisor.dev/gvisor/pkg/state
-     💣 gvisor.dev/gvisor/pkg/sync                                   from gvisor.dev/gvisor/pkg/atomicbitops+
-        gvisor.dev/gvisor/pkg/tcpip                                  from gvisor.dev/gvisor/pkg/tcpip/header+
-        gvisor.dev/gvisor/pkg/tcpip/checksum                         from gvisor.dev/gvisor/pkg/buffer+
-        gvisor.dev/gvisor/pkg/tcpip/header                           from tailscale.com/net/packet
-        gvisor.dev/gvisor/pkg/tcpip/seqnum                           from gvisor.dev/gvisor/pkg/tcpip/header
-        gvisor.dev/gvisor/pkg/waiter                                 from gvisor.dev/gvisor/pkg/context+
         k8s.io/client-go/util/homedir                                from tailscale.com/cmd/tailscale/cli
         nhooyr.io/websocket                                          from tailscale.com/derp/derphttp+
         nhooyr.io/websocket/internal/errd                            from nhooyr.io/websocket
@@ -133,7 +116,7 @@ tailscale.com/cmd/tailscale dependencies: (generated by github.com/tailscale/dep
      💣 tailscale.com/net/tshttpproxy                                from tailscale.com/derp/derphttp+
         tailscale.com/net/wsconn                                     from tailscale.com/control/controlhttp+
         tailscale.com/paths                                          from tailscale.com/cmd/tailscale/cli+
-        tailscale.com/safesocket                                     from tailscale.com/cmd/tailscale/cli+
+     💣 tailscale.com/safesocket                                     from tailscale.com/cmd/tailscale/cli+
         tailscale.com/syncs                                          from tailscale.com/net/netcheck+
         tailscale.com/tailcfg                                        from tailscale.com/cmd/tailscale/cli+
         tailscale.com/tka                                            from tailscale.com/client/tailscale+
@@ -158,7 +141,7 @@ tailscale.com/cmd/tailscale dependencies: (generated by github.com/tailscale/dep
         tailscale.com/types/views                                    from tailscale.com/tailcfg+
         tailscale.com/util/clientmetric                              from tailscale.com/net/netcheck+
         tailscale.com/util/cloudenv                                  from tailscale.com/net/dnscache+
-   W    tailscale.com/util/cmpver                                    from tailscale.com/net/tshttpproxy
+        tailscale.com/util/cmpver                                    from tailscale.com/net/tshttpproxy+
         tailscale.com/util/cmpx                                      from tailscale.com/cmd/tailscale/cli+
    L 💣 tailscale.com/util/dirwalk                                   from tailscale.com/metrics
         tailscale.com/util/dnsname                                   from tailscale.com/cmd/tailscale/cli+
@@ -169,11 +152,14 @@ tailscale.com/cmd/tailscale dependencies: (generated by github.com/tailscale/dep
         tailscale.com/util/mak                                       from tailscale.com/net/netcheck+
         tailscale.com/util/multierr                                  from tailscale.com/control/controlhttp+
         tailscale.com/util/must                                      from tailscale.com/cmd/tailscale/cli+
+        tailscale.com/util/nocasemaps                                from tailscale.com/types/ipproto
         tailscale.com/util/quarantine                                from tailscale.com/cmd/tailscale/cli
         tailscale.com/util/set                                       from tailscale.com/health+
         tailscale.com/util/singleflight                              from tailscale.com/net/dnscache
         tailscale.com/util/slicesx                                   from tailscale.com/net/dnscache+
         tailscale.com/util/testenv                                   from tailscale.com/cmd/tailscale/cli
+        tailscale.com/util/truncate                                  from tailscale.com/cmd/tailscale/cli
+        tailscale.com/util/vizerror                                  from tailscale.com/types/ipproto+
      💣 tailscale.com/util/winutil                                   from tailscale.com/hostinfo+
    W 💣 tailscale.com/util/winutil/authenticode                      from tailscale.com/clientupdate
         tailscale.com/version                                        from tailscale.com/cmd/tailscale/cli+

cmd/tailscale/tailscale_test.go

@@ -0,0 +1,21 @@
+// Copyright (c) Tailscale Inc & AUTHORS
+// SPDX-License-Identifier: BSD-3-Clause
+
+package main
+
+import (
+	"testing"
+
+	"tailscale.com/tstest/deptest"
+)
+
+func TestDeps(t *testing.T) {
+	deptest.DepChecker{
+		BadDeps: map[string]string{
+			"gvisor.dev/gvisor/pkg/buffer":       "https://github.com/tailscale/tailscale/issues/9756",
+			"gvisor.dev/gvisor/pkg/cpuid":        "https://github.com/tailscale/tailscale/issues/9756",
+			"gvisor.dev/gvisor/pkg/tcpip":        "https://github.com/tailscale/tailscale/issues/9756",
+			"gvisor.dev/gvisor/pkg/tcpip/header": "https://github.com/tailscale/tailscale/issues/9756",
+		},
+	}.Check(t)
+}

cmd/tailscaled/depaware.txt

@@ -2,11 +2,6 @@ tailscale.com/cmd/tailscaled dependencies: (generated by github.com/tailscale/de
 
         filippo.io/edwards25519                                      from github.com/hdevalence/ed25519consensus
         filippo.io/edwards25519/field                                from filippo.io/edwards25519
-   W 💣 github.com/Microsoft/go-winio                                from tailscale.com/safesocket
-   W 💣 github.com/Microsoft/go-winio/internal/fs                    from github.com/Microsoft/go-winio
-   W 💣 github.com/Microsoft/go-winio/internal/socket                from github.com/Microsoft/go-winio
-   W    github.com/Microsoft/go-winio/internal/stringbuffer          from github.com/Microsoft/go-winio/internal/fs
-   W    github.com/Microsoft/go-winio/pkg/guid                       from github.com/Microsoft/go-winio+
    W 💣 github.com/alexbrainman/sspi                                 from github.com/alexbrainman/sspi/internal/common+
    W    github.com/alexbrainman/sspi/internal/common                 from github.com/alexbrainman/sspi/negotiate
    W 💣 github.com/alexbrainman/sspi/negotiate                       from tailscale.com/net/tshttpproxy
@@ -86,6 +81,7 @@ tailscale.com/cmd/tailscaled dependencies: (generated by github.com/tailscale/de
    W 💣 github.com/dblohm7/wingoes/com/automation                    from tailscale.com/util/osdiag/internal/wsc
    W    github.com/dblohm7/wingoes/internal                          from github.com/dblohm7/wingoes/com
    W 💣 github.com/dblohm7/wingoes/pe                                from tailscale.com/util/osdiag+
+  LW 💣 github.com/digitalocean/go-smbios/smbios                     from tailscale.com/posture
         github.com/fxamacker/cbor/v2                                 from tailscale.com/tka
    W 💣 github.com/go-ole/go-ole                                     from github.com/go-ole/go-ole/oleutil+
    W 💣 github.com/go-ole/go-ole/oleutil                             from tailscale.com/wgengine/winnet
@@ -99,6 +95,8 @@ tailscale.com/cmd/tailscaled dependencies: (generated by github.com/tailscale/de
    L    github.com/google/nftables/internal/parseexprfunc            from github.com/google/nftables+
    L    github.com/google/nftables/xt                                from github.com/google/nftables/expr+
         github.com/google/uuid                                       from tailscale.com/clientupdate
+        github.com/gorilla/csrf                                      from tailscale.com/client/web
+        github.com/gorilla/securecookie                              from github.com/gorilla/csrf
         github.com/hdevalence/ed25519consensus                       from tailscale.com/tka+
    L 💣 github.com/illarion/gonotify                                 from tailscale.com/net/dns
    L    github.com/insomniacslk/dhcp/dhcpv4                          from tailscale.com/net/tstun
@@ -132,10 +130,15 @@ tailscale.com/cmd/tailscaled dependencies: (generated by github.com/tailscale/de
    L    github.com/pierrec/lz4/v4/internal/lz4errors                 from github.com/pierrec/lz4/v4+
    L    github.com/pierrec/lz4/v4/internal/lz4stream                 from github.com/pierrec/lz4/v4
    L    github.com/pierrec/lz4/v4/internal/xxh32                     from github.com/pierrec/lz4/v4/internal/lz4stream
-   W    github.com/pkg/errors                                        from github.com/tailscale/certstore
+        github.com/pkg/errors                                        from github.com/gorilla/csrf
   LD    github.com/pkg/sftp                                          from tailscale.com/ssh/tailssh
   LD    github.com/pkg/sftp/internal/encoding/ssh/filexfer           from github.com/pkg/sftp
    W 💣 github.com/tailscale/certstore                               from tailscale.com/control/controlclient
+   W 💣 github.com/tailscale/go-winio                                from tailscale.com/safesocket
+   W 💣 github.com/tailscale/go-winio/internal/fs                    from github.com/tailscale/go-winio
+   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/chacha20                from github.com/tailscale/golang-x-crypto/ssh
   LD 💣 github.com/tailscale/golang-x-crypto/internal/alias          from github.com/tailscale/golang-x-crypto/chacha20
@@ -147,7 +150,9 @@ tailscale.com/cmd/tailscaled dependencies: (generated by github.com/tailscale/de
         github.com/tailscale/goupnp/scpd                             from github.com/tailscale/goupnp
         github.com/tailscale/goupnp/soap                             from github.com/tailscale/goupnp+
         github.com/tailscale/goupnp/ssdp                             from github.com/tailscale/goupnp
+        github.com/tailscale/hujson                                  from tailscale.com/ipn/conffile
    L 💣 github.com/tailscale/netlink                                 from tailscale.com/wgengine/router+
+        github.com/tailscale/web-client-prebuilt                     from tailscale.com/client/web
      💣 github.com/tailscale/wireguard-go/conn                       from github.com/tailscale/wireguard-go/device+
    W 💣 github.com/tailscale/wireguard-go/conn/winrio                from github.com/tailscale/wireguard-go/conn
      💣 github.com/tailscale/wireguard-go/device                     from tailscale.com/net/tstun+
@@ -216,10 +221,12 @@ tailscale.com/cmd/tailscaled dependencies: (generated by github.com/tailscale/de
         nhooyr.io/websocket/internal/errd                            from nhooyr.io/websocket
         nhooyr.io/websocket/internal/xsync                           from nhooyr.io/websocket
         tailscale.com                                                from tailscale.com/version
+        tailscale.com/appc                                           from tailscale.com/ipn/ipnlocal
         tailscale.com/atomicfile                                     from tailscale.com/ipn+
   LD    tailscale.com/chirp                                          from tailscale.com/cmd/tailscaled
-        tailscale.com/client/tailscale                               from tailscale.com/derp
+        tailscale.com/client/tailscale                               from tailscale.com/derp+
         tailscale.com/client/tailscale/apitype                       from tailscale.com/ipn/ipnlocal+
+        tailscale.com/client/web                                     from tailscale.com/ipn/ipnlocal
         tailscale.com/clientupdate                                   from tailscale.com/ipn/ipnlocal
         tailscale.com/clientupdate/distsign                          from tailscale.com/clientupdate
         tailscale.com/cmd/tailscaled/childproc                       from tailscale.com/ssh/tailssh+
@@ -238,6 +245,7 @@ tailscale.com/cmd/tailscaled dependencies: (generated by github.com/tailscale/de
         tailscale.com/health/healthmsg                               from tailscale.com/ipn/ipnlocal
         tailscale.com/hostinfo                                       from tailscale.com/control/controlclient+
         tailscale.com/ipn                                            from tailscale.com/ipn/ipnlocal+
+        tailscale.com/ipn/conffile                                   from tailscale.com/cmd/tailscaled+
      💣 tailscale.com/ipn/ipnauth                                    from tailscale.com/ipn/ipnlocal+
         tailscale.com/ipn/ipnlocal                                   from tailscale.com/ssh/tailssh+
         tailscale.com/ipn/ipnserver                                  from tailscale.com/cmd/tailscaled
@@ -249,6 +257,7 @@ tailscale.com/cmd/tailscaled dependencies: (generated by github.com/tailscale/de
    L    tailscale.com/ipn/store/kubestore                            from tailscale.com/ipn/store
         tailscale.com/ipn/store/mem                                  from tailscale.com/ipn/store+
    L    tailscale.com/kube                                           from tailscale.com/ipn/store/kubestore
+        tailscale.com/licenses                                       from tailscale.com/client/web
         tailscale.com/log/filelogger                                 from tailscale.com/logpolicy
         tailscale.com/log/sockstatlog                                from tailscale.com/ipn/ipnlocal
         tailscale.com/logpolicy                                      from tailscale.com/cmd/tailscaled+
@@ -261,7 +270,7 @@ tailscale.com/cmd/tailscaled dependencies: (generated by github.com/tailscale/de
         tailscale.com/net/dns/publicdns                              from tailscale.com/net/dns/resolver+
         tailscale.com/net/dns/recursive                              from tailscale.com/net/dnsfallback
         tailscale.com/net/dns/resolvconffile                         from tailscale.com/net/dns+
-        tailscale.com/net/dns/resolver                               from tailscale.com/ipn/ipnlocal+
+        tailscale.com/net/dns/resolver                               from tailscale.com/net/dns
         tailscale.com/net/dnscache                                   from tailscale.com/control/controlclient+
         tailscale.com/net/dnsfallback                                from tailscale.com/control/controlclient+
         tailscale.com/net/flowtrack                                  from tailscale.com/net/packet+
@@ -275,6 +284,7 @@ tailscale.com/cmd/tailscaled dependencies: (generated by github.com/tailscale/de
      💣 tailscale.com/net/netstat                                    from tailscale.com/ipn/ipnauth+
         tailscale.com/net/netutil                                    from tailscale.com/ipn/ipnlocal+
         tailscale.com/net/packet                                     from tailscale.com/net/tstun+
+        tailscale.com/net/packet/checksum                            from tailscale.com/net/tstun
         tailscale.com/net/ping                                       from tailscale.com/net/netcheck+
         tailscale.com/net/portmapper                                 from tailscale.com/net/netcheck+
         tailscale.com/net/proxymux                                   from tailscale.com/cmd/tailscaled
@@ -292,13 +302,14 @@ tailscale.com/cmd/tailscaled dependencies: (generated by github.com/tailscale/de
         tailscale.com/net/wsconn                                     from tailscale.com/control/controlhttp+
         tailscale.com/paths                                          from tailscale.com/ipn/ipnlocal+
      💣 tailscale.com/portlist                                       from tailscale.com/ipn/ipnlocal
+        tailscale.com/posture                                        from tailscale.com/ipn/ipnlocal
         tailscale.com/proxymap                                       from tailscale.com/tsd+
-        tailscale.com/safesocket                                     from tailscale.com/client/tailscale+
+     💣 tailscale.com/safesocket                                     from tailscale.com/client/tailscale+
         tailscale.com/smallzstd                                      from tailscale.com/control/controlclient+
   LD 💣 tailscale.com/ssh/tailssh                                    from tailscale.com/cmd/tailscaled
         tailscale.com/syncs                                          from tailscale.com/net/netcheck+
         tailscale.com/tailcfg                                        from tailscale.com/client/tailscale/apitype+
-        tailscale.com/taildrop                                       from tailscale.com/ipn/ipnlocal
+        tailscale.com/taildrop                                       from tailscale.com/ipn/ipnlocal+
      💣 tailscale.com/tempfork/device                                from tailscale.com/net/tstun/table
   LD    tailscale.com/tempfork/gliderlabs/ssh                        from tailscale.com/ssh/tailssh
         tailscale.com/tempfork/heap                                  from tailscale.com/wgengine/magicsock
@@ -309,6 +320,7 @@ tailscale.com/cmd/tailscaled dependencies: (generated by github.com/tailscale/de
         tailscale.com/tstime/mono                                    from tailscale.com/net/tstun+
         tailscale.com/tstime/rate                                    from tailscale.com/wgengine/filter+
         tailscale.com/tsweb/varz                                     from tailscale.com/cmd/tailscaled
+        tailscale.com/types/appctype                                 from tailscale.com/ipn/ipnlocal
         tailscale.com/types/dnstype                                  from tailscale.com/ipn/ipnlocal+
         tailscale.com/types/empty                                    from tailscale.com/ipn+
         tailscale.com/types/flagtype                                 from tailscale.com/cmd/tailscaled
@@ -329,24 +341,25 @@ tailscale.com/cmd/tailscaled dependencies: (generated by github.com/tailscale/de
         tailscale.com/types/views                                    from tailscale.com/ipn/ipnlocal+
         tailscale.com/util/clientmetric                              from tailscale.com/control/controlclient+
         tailscale.com/util/cloudenv                                  from tailscale.com/net/dns/resolver+
-  LW    tailscale.com/util/cmpver                                    from tailscale.com/net/dns+
+        tailscale.com/util/cmpver                                    from tailscale.com/net/dns+
         tailscale.com/util/cmpx                                      from tailscale.com/derp/derphttp+
      💣 tailscale.com/util/deephash                                  from tailscale.com/ipn/ipnlocal+
    L 💣 tailscale.com/util/dirwalk                                   from tailscale.com/metrics+
         tailscale.com/util/dnsname                                   from tailscale.com/hostinfo+
         tailscale.com/util/goroutines                                from tailscale.com/ipn/ipnlocal
-        tailscale.com/util/groupmember                               from tailscale.com/ipn/ipnauth
+        tailscale.com/util/groupmember                               from tailscale.com/ipn/ipnauth+
      💣 tailscale.com/util/hashx                                     from tailscale.com/util/deephash
+        tailscale.com/util/httphdr                                   from tailscale.com/ipn/ipnlocal+
         tailscale.com/util/httpm                                     from tailscale.com/client/tailscale+
         tailscale.com/util/lineread                                  from tailscale.com/hostinfo+
    L    tailscale.com/util/linuxfw                                   from tailscale.com/net/netns+
         tailscale.com/util/mak                                       from tailscale.com/control/controlclient+
         tailscale.com/util/multierr                                  from tailscale.com/control/controlclient+
         tailscale.com/util/must                                      from tailscale.com/logpolicy+
+        tailscale.com/util/nocasemaps                                from tailscale.com/types/ipproto
      💣 tailscale.com/util/osdiag                                    from tailscale.com/cmd/tailscaled+
    W 💣 tailscale.com/util/osdiag/internal/wsc                       from tailscale.com/util/osdiag
         tailscale.com/util/osshare                                   from tailscale.com/ipn/ipnlocal+
-   W    tailscale.com/util/pidowner                                  from tailscale.com/ipn/ipnauth
         tailscale.com/util/race                                      from tailscale.com/net/dns/resolver
         tailscale.com/util/racebuild                                 from tailscale.com/logpolicy
         tailscale.com/util/rands                                     from tailscale.com/ipn/ipnlocal+
@@ -354,12 +367,13 @@ tailscale.com/cmd/tailscaled dependencies: (generated by github.com/tailscale/de
         tailscale.com/util/set                                       from tailscale.com/health+
         tailscale.com/util/singleflight                              from tailscale.com/control/controlclient+
         tailscale.com/util/slicesx                                   from tailscale.com/net/dnscache+
-   W    tailscale.com/util/syspolicy                                 from tailscale.com/cmd/tailscaled
+        tailscale.com/util/syspolicy                                 from tailscale.com/cmd/tailscaled+
         tailscale.com/util/sysresources                              from tailscale.com/wgengine/magicsock
         tailscale.com/util/systemd                                   from tailscale.com/control/controlclient+
         tailscale.com/util/testenv                                   from tailscale.com/ipn/ipnlocal+
         tailscale.com/util/uniq                                      from tailscale.com/wgengine/magicsock+
-     💣 tailscale.com/util/winutil                                   from tailscale.com/control/controlclient+
+        tailscale.com/util/vizerror                                  from tailscale.com/types/ipproto+
+     💣 tailscale.com/util/winutil                                   from tailscale.com/clientupdate+
    W 💣 tailscale.com/util/winutil/authenticode                      from tailscale.com/util/osdiag+
    W    tailscale.com/util/winutil/policy                            from tailscale.com/ipn/ipnlocal
         tailscale.com/version                                        from tailscale.com/derp+
@@ -386,7 +400,7 @@ tailscale.com/cmd/tailscaled dependencies: (generated by github.com/tailscale/de
         golang.org/x/crypto/cryptobyte                               from crypto/ecdsa+
         golang.org/x/crypto/cryptobyte/asn1                          from crypto/ecdsa+
         golang.org/x/crypto/curve25519                               from github.com/tailscale/golang-x-crypto/ssh+
-  LD    golang.org/x/crypto/ed25519                                  from golang.org/x/crypto/ssh+
+  LD    golang.org/x/crypto/ed25519                                  from github.com/tailscale/golang-x-crypto/ssh
         golang.org/x/crypto/hkdf                                     from crypto/tls+
         golang.org/x/crypto/nacl/box                                 from tailscale.com/types/key
         golang.org/x/crypto/nacl/secretbox                           from golang.org/x/crypto/nacl/box
@@ -462,6 +476,7 @@ tailscale.com/cmd/tailscaled dependencies: (generated by github.com/tailscale/de
         encoding/base32                                              from tailscale.com/tka+
         encoding/base64                                              from encoding/json+
         encoding/binary                                              from compress/gzip+
+        encoding/gob                                                 from github.com/gorilla/securecookie
         encoding/hex                                                 from crypto/x509+
         encoding/json                                                from expvar+
         encoding/pem                                                 from crypto/tls+
@@ -476,6 +491,7 @@ tailscale.com/cmd/tailscaled dependencies: (generated by github.com/tailscale/de
         hash/fnv                                                     from tailscale.com/wgengine/magicsock+
         hash/maphash                                                 from go4.org/mem
         html                                                         from tailscale.com/ipn/ipnlocal+
+        html/template                                                from github.com/gorilla/csrf
         io                                                           from bufio+
         io/fs                                                        from crypto/x509+
         io/ioutil                                                    from github.com/godbus/dbus/v5+
@@ -520,6 +536,8 @@ tailscale.com/cmd/tailscaled dependencies: (generated by github.com/tailscale/de
         sync/atomic                                                  from context+
         syscall                                                      from crypto/rand+
         text/tabwriter                                               from runtime/pprof
+        text/template                                                from html/template
+        text/template/parse                                          from html/template+
         time                                                         from compress/gzip+
         unicode                                                      from bytes+
         unicode/utf16                                                from crypto/x509+

cmd/tailscaled/tailscaled.go

@@ -29,9 +29,11 @@ import (
 	"syscall"
 	"time"
 
+	"tailscale.com/client/tailscale"
 	"tailscale.com/cmd/tailscaled/childproc"
 	"tailscale.com/control/controlclient"
 	"tailscale.com/envknob"
+	"tailscale.com/ipn/conffile"
 	"tailscale.com/ipn/ipnlocal"
 	"tailscale.com/ipn/ipnserver"
 	"tailscale.com/ipn/store"
@@ -127,6 +129,7 @@ var args struct {
 	tunname string
 
 	cleanup        bool
+	confFile       string
 	debug          string
 	port           uint16
 	statepath      string
@@ -172,6 +175,7 @@ func main() {
 	flag.StringVar(&args.birdSocketPath, "bird-socket", "", "path of the bird unix socket")
 	flag.BoolVar(&printVersion, "version", false, "print version information and exit")
 	flag.BoolVar(&args.disableLogs, "no-logs-no-support", false, "disable log uploads; this also disables any technical support")
+	flag.StringVar(&args.confFile, "config", "", "path to config file")
 
 	if len(os.Args) > 0 && filepath.Base(os.Args[0]) == "tailscale" && beCLI != nil {
 		beCLI()
@@ -339,6 +343,17 @@ func run() error {
 
 	sys := new(tsd.System)
 
+	// Parse config, if specified, to fail early if it's invalid.
+	var conf *conffile.Config
+	if args.confFile != "" {
+		var err error
+		conf, err = conffile.Load(args.confFile)
+		if err != nil {
+			return fmt.Errorf("error reading config file: %w", err)
+		}
+		sys.InitialConfig = conf
+	}
+
 	netMon, err := netmon.New(func(format string, args ...any) {
 		logf(format, args...)
 	})
@@ -540,6 +555,10 @@ func getLocalBackend(ctx context.Context, logf logger.Logf, logID logid.PublicID
 	}
 	sys.Set(store)
 
+	if w, ok := sys.Tun.GetOK(); ok {
+		w.Start()
+	}
+
 	lb, err := ipnlocal.NewLocalBackend(logf, logID, sys, opts.LoginFlags)
 	if err != nil {
 		return nil, fmt.Errorf("ipnlocal.NewLocalBackend: %w", err)
@@ -551,6 +570,7 @@ func getLocalBackend(ctx context.Context, logf logger.Logf, logID logid.PublicID
 	if root := lb.TailscaleVarRoot(); root != "" {
 		dnsfallback.SetCachePath(filepath.Join(root, "derpmap.cached.json"), logf)
 	}
+	lb.SetWebLocalClient(&tailscale.LocalClient{Socket: args.socketpath, UseSocketOnly: args.socketpath != ""})
 	configureTaildrop(logf, lb)
 	if err := ns.Start(lb); err != nil {
 		log.Fatalf("failed to start netstack: %v", err)

cmd/tailscaled/tailscaled_windows.go

@@ -30,6 +30,7 @@ import (
 	"os"
 	"os/exec"
 	"os/signal"
+	"path/filepath"
 	"sync"
 	"syscall"
 	"time"
@@ -299,6 +300,14 @@ func beWindowsSubprocess() bool {
 		}
 	}()
 
+	// Pre-load wintun.dll using a fully-qualified path so that wintun-go
+	// loads our copy and not some (possibly outdated) copy dropped in system32.
+	// (OSS Issue #10023)
+	fqWintunPath := fullyQualifiedWintunPath(log.Printf)
+	if _, err := windows.LoadDLL(fqWintunPath); err != nil {
+		log.Printf("Error pre-loading \"%s\": %v", fqWintunPath, err)
+	}
+
 	sys := new(tsd.System)
 	netMon, err := netmon.New(log.Printf)
 	if err != nil {
@@ -507,7 +516,7 @@ func babysitProc(ctx context.Context, args []string, logf logger.Logf) {
 }
 
 func uninstallWinTun(logf logger.Logf) {
-	dll := windows.NewLazyDLL("wintun.dll")
+	dll := windows.NewLazyDLL(fullyQualifiedWintunPath(logf))
 	if err := dll.Load(); err != nil {
 		logf("Cannot load wintun.dll for uninstall: %v", err)
 		return
@@ -517,3 +526,16 @@ func uninstallWinTun(logf logger.Logf) {
 	err := wintun.Uninstall()
 	logf("Uninstall: %v", err)
 }
+
+func fullyQualifiedWintunPath(logf logger.Logf) string {
+	var dir string
+	var buf [windows.MAX_PATH]uint16
+	length := uint32(len(buf))
+	if err := windows.QueryFullProcessImageName(windows.CurrentProcess(), 0, &buf[0], &length); err != nil {
+		logf("QueryFullProcessImageName failed: %v", err)
+	} else {
+		dir = filepath.Dir(windows.UTF16ToString(buf[:length]))
+	}
+
+	return filepath.Join(dir, "wintun.dll")
+}

cmd/testwrapper/args.go

@@ -0,0 +1,130 @@
+// Copyright (c) Tailscale Inc & AUTHORS
+// SPDX-License-Identifier: BSD-3-Clause
+
+package main
+
+import (
+	"flag"
+	"io"
+	"os"
+	"slices"
+	"strings"
+	"testing"
+)
+
+// defaultTestArgs contains the default values for all flags in the testing
+// package. It is used to reset the flag values in testwrapper tests to allow
+// parsing the flags again.
+var defaultTestArgs map[string]string
+
+// initDefaultTestArgs initializes defaultTestArgs.
+func initDefaultTestArgs() {
+	if defaultTestArgs != nil {
+		return
+	}
+	defaultTestArgs = make(map[string]string)
+	flag.CommandLine.VisitAll(func(f *flag.Flag) {
+		defaultTestArgs[f.Name] = f.DefValue
+	})
+}
+
+// registerTestFlags registers all flags from the testing package with the
+// provided flag set. It does so by calling testing.Init() and then iterating
+// over all flags registered on flag.CommandLine.
+func registerTestFlags(fs *flag.FlagSet) {
+	testing.Init()
+	type bv interface {
+		IsBoolFlag() bool
+	}
+
+	flag.CommandLine.VisitAll(func(f *flag.Flag) {
+		if b, ok := f.Value.(bv); ok && b.IsBoolFlag() {
+			fs.Bool(f.Name, f.DefValue == "true", f.Usage)
+			if name, ok := strings.CutPrefix(f.Name, "test."); ok {
+				fs.Bool(name, f.DefValue == "true", f.Usage)
+			}
+			return
+		}
+
+		// We don't actually care about the value of the flag, so we just
+		// register it as a string. The values will be passed to `go test` which
+		// will parse and validate them anyway.
+		fs.String(f.Name, f.DefValue, f.Usage)
+		if name, ok := strings.CutPrefix(f.Name, "test."); ok {
+			fs.String(name, f.DefValue, f.Usage)
+		}
+	})
+}
+
+// splitArgs splits args into three parts as consumed by go test.
+//
+//	go test [build/test flags] [packages] [build/test flags & test binary flags]
+//
+// We return these as three slices of strings [pre] [pkgs] [post].
+//
+// It is used to split the arguments passed to testwrapper into the arguments
+// passed to go test and the arguments passed to the tests.
+func splitArgs(args []string) (pre, pkgs, post []string, _ error) {
+	if len(args) == 0 {
+		return nil, nil, nil, nil
+	}
+
+	fs := newTestFlagSet()
+	// Parse stops at the first non-flag argument, so this allows us
+	// to parse those as values and then reconstruct them as args.
+	if err := fs.Parse(args); err != nil {
+		return nil, nil, nil, err
+	}
+	fs.Visit(func(f *flag.Flag) {
+		if f.Value.String() != f.DefValue && f.DefValue != "false" {
+			pre = append(pre, "-"+f.Name, f.Value.String())
+		} else {
+			pre = append(pre, "-"+f.Name)
+		}
+	})
+
+	// fs.Args() now contains [packages]+[build/test flags & test binary flags],
+	// to split it we need to find the first non-flag argument.
+	rem := fs.Args()
+	ix := slices.IndexFunc(rem, func(s string) bool { return strings.HasPrefix(s, "-") })
+	if ix == -1 {
+		return pre, rem, nil, nil
+	}
+	pkgs = rem[:ix]
+	post = rem[ix:]
+	return pre, pkgs, post, nil
+}
+
+func newTestFlagSet() *flag.FlagSet {
+	fs := flag.NewFlagSet("testwrapper", flag.ContinueOnError)
+	fs.SetOutput(io.Discard)
+
+	// Register all flags from the testing package.
+	registerTestFlags(fs)
+	// Also register the -exec flag, which is not part of the testing package.
+	// TODO(maisem): figure out what other flags we need to register explicitly.
+	fs.String("exec", "", "Command to run tests with")
+	fs.Bool("race", false, "build with race detector")
+	return fs
+}
+
+// testingVerbose reports whether the test is being run with verbose logging.
+var testingVerbose = func() bool {
+	verbose := false
+
+	// Likely doesn't matter, but to be correct follow the go flag parsing logic
+	// of overriding previous values.
+	for _, arg := range os.Args[1:] {
+		switch arg {
+		case "-test.v", "--test.v",
+			"-test.v=true", "--test.v=true",
+			"-v", "--v",
+			"-v=true", "--v=true":
+			verbose = true
+		case "-test.v=false", "--test.v=false",
+			"-v=false", "--v=false":
+			verbose = false
+		}
+	}
+	return verbose
+}()

cmd/testwrapper/args_test.go

@@ -0,0 +1,97 @@
+// Copyright (c) Tailscale Inc & AUTHORS
+// SPDX-License-Identifier: BSD-3-Clause
+
+package main
+
+import (
+	"slices"
+	"testing"
+)
+
+func TestSplitArgs(t *testing.T) {
+	tests := []struct {
+		name            string
+		in              []string
+		pre, pkgs, post []string
+	}{
+		{
+			name: "empty",
+		},
+		{
+			name: "all",
+			in:   []string{"-v", "pkg1", "pkg2", "-run", "TestFoo", "-timeout=20s"},
+			pre:  []string{"-v"},
+			pkgs: []string{"pkg1", "pkg2"},
+			post: []string{"-run", "TestFoo", "-timeout=20s"},
+		},
+		{
+			name: "only_pkgs",
+			in:   []string{"./..."},
+			pkgs: []string{"./..."},
+		},
+		{
+			name: "pkgs_and_post",
+			in:   []string{"pkg1", "-run", "TestFoo"},
+			pkgs: []string{"pkg1"},
+			post: []string{"-run", "TestFoo"},
+		},
+		{
+			name: "pkgs_and_post",
+			in:   []string{"-v", "pkg2"},
+			pre:  []string{"-v"},
+			pkgs: []string{"pkg2"},
+		},
+		{
+			name: "only_args",
+			in:   []string{"-v", "-run=TestFoo"},
+			pre:  []string{"-run", "TestFoo", "-v"}, // sorted
+		},
+		{
+			name: "space_in_pre_arg",
+			in:   []string{"-run", "TestFoo", "./cmd/testwrapper"},
+			pre:  []string{"-run", "TestFoo"},
+			pkgs: []string{"./cmd/testwrapper"},
+		},
+		{
+			name: "space_in_arg",
+			in:   []string{"-exec", "sudo -E", "./cmd/testwrapper"},
+			pre:  []string{"-exec", "sudo -E"},
+			pkgs: []string{"./cmd/testwrapper"},
+		},
+		{
+			name: "test-arg",
+			in:   []string{"-exec", "sudo -E", "./cmd/testwrapper", "--", "--some-flag"},
+			pre:  []string{"-exec", "sudo -E"},
+			pkgs: []string{"./cmd/testwrapper"},
+			post: []string{"--", "--some-flag"},
+		},
+		{
+			name: "dupe-args",
+			in:   []string{"-v", "-v", "-race", "-race", "./cmd/testwrapper", "--", "--some-flag"},
+			pre:  []string{"-race", "-v"},
+			pkgs: []string{"./cmd/testwrapper"},
+			post: []string{"--", "--some-flag"},
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			pre, pkgs, post, err := splitArgs(tt.in)
+			if err != nil {
+				t.Fatal(err)
+			}
+			if !slices.Equal(pre, tt.pre) {
+				t.Errorf("pre = %q; want %q", pre, tt.pre)
+			}
+			if !slices.Equal(pkgs, tt.pkgs) {
+				t.Errorf("pattern = %q; want %q", pkgs, tt.pkgs)
+			}
+			if !slices.Equal(post, tt.post) {
+				t.Errorf("post = %q; want %q", post, tt.post)
+			}
+			if t.Failed() {
+				t.Logf("SplitArgs(%q) = %q %q %q", tt.in, pre, pkgs, post)
+			}
+		})
+	}
+}

cmd/testwrapper/testwrapper.go

@@ -13,7 +13,6 @@ import (
 	"context"
 	"encoding/json"
 	"errors"
-	"flag"
 	"fmt"
 	"io"
 	"log"
@@ -71,18 +70,24 @@ var debug = os.Getenv("TS_TESTWRAPPER_DEBUG") != ""
 // set to true. Package build errors will not emit a testAttempt (as no valid
 // JSON is produced) but the [os/exec.ExitError] will be returned.
 // It calls close(ch) when it's done.
-func runTests(ctx context.Context, attempt int, pt *packageTests, otherArgs []string, ch chan<- *testAttempt) error {
+func runTests(ctx context.Context, attempt int, pt *packageTests, goTestArgs, testArgs []string, ch chan<- *testAttempt) error {
 	defer close(ch)
-	args := []string{"test", "-json", pt.Pattern}
-	args = append(args, otherArgs...)
+	args := []string{"test"}
+	args = append(args, goTestArgs...)
+	args = append(args, pt.Pattern)
 	if len(pt.Tests) > 0 {
 		runArg := strings.Join(pt.Tests, "|")
-		args = append(args, "-run", runArg)
+		args = append(args, "--run", runArg)
 	}
+	args = append(args, testArgs...)
+	args = append(args, "-json")
 	if debug {
 		fmt.Println("running", strings.Join(args, " "))
 	}
 	cmd := exec.CommandContext(ctx, "go", args...)
+	if len(pt.Tests) > 0 {
+		cmd.Env = append(os.Environ(), "TS_TEST_SHARD=") // clear test shard; run all tests we say to run
+	}
 	r, err := cmd.StdoutPipe()
 	if err != nil {
 		log.Printf("error creating stdout pipe: %v", err)
@@ -178,54 +183,28 @@ func runTests(ctx context.Context, attempt int, pt *packageTests, otherArgs []st
 }
 
 func main() {
+	goTestArgs, packages, testArgs, err := splitArgs(os.Args[1:])
+	if err != nil {
+		log.Fatal(err)
+		return
+	}
+	if len(packages) == 0 {
+		fmt.Println("testwrapper: no packages specified")
+		return
+	}
+
 	ctx := context.Background()
-
-	// We only need to parse the -v flag to figure out whether to print the logs
-	// for a test. We don't need to parse any other flags, so we just use the
-	// flag package to parse the -v flag and then pass the rest of the args
-	// through to 'go test'.
-	// We run `go test -json` which returns the same information as `go test -v`,
-	// but in a machine-readable format. So this flag is only for testwrapper's
-	// output.
-	v := flag.Bool("v", false, "verbose")
-
-	flag.Usage = func() {
-		fmt.Println("usage: testwrapper [testwrapper-flags] [pattern] [build/test flags & test binary flags]")
-		fmt.Println()
-		fmt.Println("testwrapper-flags:")
-		flag.CommandLine.PrintDefaults()
-		fmt.Println()
-		fmt.Println("examples:")
-		fmt.Println("\ttestwrapper -v ./... -count=1")
-		fmt.Println("\ttestwrapper ./pkg/foo -run TestBar -count=1")
-		fmt.Println()
-		fmt.Println("Unlike 'go test', testwrapper requires a package pattern as the first positional argument and only supports a single pattern.")
-	}
-	flag.Parse()
-
-	args := flag.Args()
-	if len(args) < 1 || strings.HasPrefix(args[0], "-") {
-		fmt.Println("no pattern specified")
-		flag.Usage()
-		os.Exit(1)
-	} else if len(args) > 1 && !strings.HasPrefix(args[1], "-") {
-		fmt.Println("expected single pattern")
-		flag.Usage()
-		os.Exit(1)
-	}
-	pattern, otherArgs := args[0], args[1:]
-
 	type nextRun struct {
 		tests   []*packageTests
 		attempt int // starting at 1
 	}
-
-	toRun := []*nextRun{
-		{
-			tests:   []*packageTests{{Pattern: pattern}},
-			attempt: 1,
-		},
+	firstRun := &nextRun{
+		attempt: 1,
 	}
+	for _, pkg := range packages {
+		firstRun.tests = append(firstRun.tests, &packageTests{Pattern: pkg})
+	}
+	toRun := []*nextRun{firstRun}
 	printPkgOutcome := func(pkg, outcome string, attempt int) {
 		if outcome == "skip" {
 			fmt.Printf("?\t%s [skipped/no tests] \n", pkg)
@@ -263,7 +242,7 @@ func main() {
 			runErr := make(chan error, 1)
 			go func() {
 				defer close(runErr)
-				runErr <- runTests(ctx, thisRun.attempt, pt, otherArgs, ch)
+				runErr <- runTests(ctx, thisRun.attempt, pt, goTestArgs, testArgs, ch)
 			}()
 
 			var failed bool
@@ -273,7 +252,7 @@ func main() {
 				// convenient for us to to specify files in tests, so fix tr.pkg
 				// so that subsequent testwrapper attempts run correctly.
 				if tr.pkg == "command-line-arguments" {
-					tr.pkg = pattern
+					tr.pkg = packages[0]
 				}
 				if tr.pkgFinished {
 					if tr.outcome == "fail" && len(toRetry[tr.pkg]) == 0 {
@@ -285,7 +264,7 @@ func main() {
 					printPkgOutcome(tr.pkg, tr.outcome, thisRun.attempt)
 					continue
 				}
-				if *v || tr.outcome == "fail" {
+				if testingVerbose || tr.outcome == "fail" {
 					io.Copy(os.Stdout, &tr.logs)
 				}
 				if tr.outcome != "fail" {

cmd/tsconnect/wasm/wasm_js.go

@@ -125,6 +125,7 @@ func newIPN(jsConfig js.Value) map[string]any {
 		return ns.DialContextTCP(ctx, dst)
 	}
 	sys.NetstackRouter.Set(true)
+	sys.Tun.Get().Start()
 
 	logid := lpc.PublicID
 	srv := ipnserver.New(logf, logid, sys.NetMon.Get())

control/controlclient/auto.go

@@ -481,7 +481,7 @@ func (mrs mapRoutineState) UpdateNetmapDelta(muts []netmap.NodeMutation) bool {
 // control server, and keeping the netmap up to date.
 func (c *Auto) mapRoutine() {
 	defer close(c.mapDone)
-	mrs := &mapRoutineState{
+	mrs := mapRoutineState{
 		c:  c,
 		bo: backoff.NewBackoff("mapRoutine", c.logf, 30*time.Second),
 	}

control/controlclient/direct.go

@@ -55,6 +55,7 @@ import (
 	"tailscale.com/util/clientmetric"
 	"tailscale.com/util/multierr"
 	"tailscale.com/util/singleflight"
+	"tailscale.com/util/syspolicy"
 	"tailscale.com/util/systemd"
 )
 
@@ -66,7 +67,6 @@ type Direct struct {
 	controlKnobs          *controlknobs.Knobs // always non-nil
 	serverURL             string              // URL of the tailcontrol server
 	clock                 tstime.Clock
-	lastPrintMap          time.Time
 	logf                  logger.Logf
 	netMon                *netmon.Monitor // or nil
 	discoPubKey           key.DiscoPublic
@@ -566,6 +566,11 @@ func (c *Direct) doLogin(ctx context.Context, opt loginOpt) (mustRegen bool, new
 		err = errors.New("hostinfo: BackendLogID missing")
 		return regen, opt.URL, nil, err
 	}
+
+	tailnet, err := syspolicy.GetString(syspolicy.Tailnet, "")
+	if err != nil {
+		c.logf("unable to provide Tailnet field in register request. err: %v", err)
+	}
 	now := c.clock.Now().Round(time.Second)
 	request := tailcfg.RegisterRequest{
 		Version:          1,
@@ -577,6 +582,7 @@ func (c *Direct) doLogin(ctx context.Context, opt loginOpt) (mustRegen bool, new
 		Timestamp:        &now,
 		Ephemeral:        (opt.Flags & LoginEphemeral) != 0,
 		NodeKeySignature: nodeKeySignature,
+		Tailnet:          tailnet,
 	}
 	if opt.Logout {
 		request.Expiry = time.Unix(123, 0) // far in the past
@@ -822,7 +828,7 @@ const watchdogTimeout = 120 * time.Second
 // if the context expires or the server returns an error/closes the connection
 // and as such always returns a non-nil error.
 //
-// If cb is nil, OmitPeers will be set to true.
+// If nu is nil, OmitPeers will be set to true.
 func (c *Direct) sendMapRequest(ctx context.Context, isStreaming bool, nu NetmapUpdater) error {
 	if isStreaming && nu == nil {
 		panic("cb must be non-nil if isStreaming is true")
@@ -962,8 +968,6 @@ func (c *Direct) sendMapRequest(ctx context.Context, isStreaming bool, nu Netmap
 		return nil
 	}
 
-	var mapResIdx int // 0 for first message, then 1+ for deltas
-
 	sess := newMapSession(persist.PrivateNodeKey(), nu, c.controlKnobs)
 	defer sess.Close()
 	sess.cancel = cancel
@@ -972,17 +976,6 @@ func (c *Direct) sendMapRequest(ctx context.Context, isStreaming bool, nu Netmap
 	sess.altClock = c.clock
 	sess.machinePubKey = machinePubKey
 	sess.onDebug = c.handleDebugMessage
-	sess.onConciseNetMapSummary = func(summary string) {
-		// Occasionally print the netmap header.
-		// This is handy for debugging, and our logs processing
-		// pipeline depends on it. (TODO: Remove this dependency.)
-		now := c.clock.Now()
-		if now.Sub(c.lastPrintMap) < 5*time.Minute {
-			return
-		}
-		c.lastPrintMap = now
-		c.logf("[v1] new network map[%d]:\n%s", mapResIdx, summary)
-	}
 	sess.onSelfNodeChanged = func(nm *netmap.NetworkMap) {
 		c.mu.Lock()
 		defer c.mu.Unlock()
@@ -999,7 +992,27 @@ func (c *Direct) sendMapRequest(ctx context.Context, isStreaming bool, nu Netmap
 		}
 		c.expiry = nm.Expiry
 	}
-	sess.StartWatchdog()
+
+	// Create a watchdog timer that breaks the connection if we don't receive a
+	// MapResponse from the network at least once every two minutes. The
+	// watchdog timer is stopped every time we receive a MapResponse (so it
+	// doesn't run when we're processing a MapResponse message, including any
+	// long-running requested operations like Debug.Sleep) and is reset whenever
+	// we go back to blocking on network reads.
+	watchdogTimer, watchdogTimedOut := c.clock.NewTimer(watchdogTimeout)
+	defer watchdogTimer.Stop()
+
+	go func() {
+		select {
+		case <-ctx.Done():
+			vlogf("netmap: ending timeout goroutine")
+			return
+		case <-watchdogTimedOut:
+			c.logf("map response long-poll timed out!")
+			cancel()
+			return
+		}
+	}()
 
 	// gotNonKeepAliveMessage is whether we've yet received a MapResponse message without
 	// KeepAlive set.
@@ -1012,7 +1025,8 @@ func (c *Direct) sendMapRequest(ctx context.Context, isStreaming bool, nu Netmap
 	// the same format before just closing the connection.
 	// We can use this same read loop either way.
 	var msg []byte
-	for ; mapResIdx == 0 || isStreaming; mapResIdx++ {
+	for mapResIdx := 0; mapResIdx == 0 || isStreaming; mapResIdx++ {
+		watchdogTimer.Reset(watchdogTimeout)
 		vlogf("netmap: starting size read after %v (poll %v)", time.Since(t0).Round(time.Millisecond), mapResIdx)
 		var siz [4]byte
 		if _, err := io.ReadFull(res.Body, siz[:]); err != nil {
@@ -1033,6 +1047,7 @@ func (c *Direct) sendMapRequest(ctx context.Context, isStreaming bool, nu Netmap
 			vlogf("netmap: decode error: %v")
 			return err
 		}
+		watchdogTimer.Stop()
 
 		metricMapResponseMessages.Add(1)
 
@@ -1075,14 +1090,6 @@ func (c *Direct) sendMapRequest(ctx context.Context, isStreaming bool, nu Netmap
 				c.logf("netmap: [unexpected] new dial plan; nowhere to store it")
 			}
 		}
-
-		select {
-		case sess.watchdogReset <- struct{}{}:
-			vlogf("netmap: sent timer reset")
-		case <-ctx.Done():
-			c.logf("[v1] netmap: not resetting timer; context done: %v", ctx.Err())
-			return ctx.Err()
-		}
 		if resp.KeepAlive {
 			metricMapResponseKeepAlives.Add(1)
 			continue
@@ -1109,7 +1116,7 @@ func (c *Direct) sendMapRequest(ctx context.Context, isStreaming bool, nu Netmap
 	return nil
 }
 
-func (c *Direct) handleDebugMessage(ctx context.Context, debug *tailcfg.Debug, watchdogReset chan<- struct{}) error {
+func (c *Direct) handleDebugMessage(ctx context.Context, debug *tailcfg.Debug) error {
 	if code := debug.Exit; code != nil {
 		c.logf("exiting process with status %v per controlplane", *code)
 		os.Exit(*code)
@@ -1119,7 +1126,7 @@ func (c *Direct) handleDebugMessage(ctx context.Context, debug *tailcfg.Debug, w
 		envknob.SetNoLogsNoSupport()
 	}
 	if sleep := time.Duration(debug.SleepSeconds * float64(time.Second)); sleep > 0 {
-		if err := sleepAsRequested(ctx, c.logf, watchdogReset, sleep, c.clock); err != nil {
+		if err := sleepAsRequested(ctx, c.logf, sleep, c.clock); err != nil {
 			return err
 		}
 	}
@@ -1451,7 +1458,7 @@ func answerC2NPing(logf logger.Logf, c2nHandler http.Handler, c *http.Client, pr
 // that the client sleep. The complication is that while we're sleeping (if for
 // a long time), we need to periodically reset the watchdog timer before it
 // expires.
-func sleepAsRequested(ctx context.Context, logf logger.Logf, watchdogReset chan<- struct{}, d time.Duration, clock tstime.Clock) error {
+func sleepAsRequested(ctx context.Context, logf logger.Logf, d time.Duration, clock tstime.Clock) error {
 	const maxSleep = 5 * time.Minute
 	if d > maxSleep {
 		logf("sleeping for %v, capped from server-requested %v ...", maxSleep, d)
@@ -1460,25 +1467,13 @@ func sleepAsRequested(ctx context.Context, logf logger.Logf, watchdogReset chan<
 		logf("sleeping for server-requested %v ...", d)
 	}
 
-	ticker, tickerChannel := clock.NewTicker(watchdogTimeout / 2)
-	defer ticker.Stop()
 	timer, timerChannel := clock.NewTimer(d)
 	defer timer.Stop()
-	for {
-		select {
-		case <-ctx.Done():
-			return ctx.Err()
-		case <-timerChannel:
-			return nil
-		case <-tickerChannel:
-			select {
-			case watchdogReset <- struct{}{}:
-			case <-timerChannel:
-				return nil
-			case <-ctx.Done():
-				return ctx.Err()
-			}
-		}
+	select {
+	case <-ctx.Done():
+		return ctx.Err()
+	case <-timerChannel:
+		return nil
 	}
 }
 

control/controlclient/map.go

@@ -49,7 +49,6 @@ type mapSession struct {
 	machinePubKey  key.MachinePublic
 	altClock       tstime.Clock       // if nil, regular time is used
 	cancel         context.CancelFunc // always non-nil, shuts down caller's base long poll context
-	watchdogReset  chan struct{}      // send to request that the long poll activity watchdog timeout be reset
 
 	// sessionAliveCtx is a Background-based context that's alive for the
 	// duration of the mapSession that we own the lifetime of. It's closed by
@@ -57,22 +56,19 @@ type mapSession struct {
 	sessionAliveCtx      context.Context
 	sessionAliveCtxClose context.CancelFunc // closes sessionAliveCtx
 
-	// Optional hooks, set once before use.
+	// Optional hooks, guaranteed non-nil (set to no-op funcs) by the
+	// newMapSession constructor. They must be overridden if desired
+	// before the mapSession is used.
 
 	// onDebug specifies what to do with a *tailcfg.Debug message.
-	// If the watchdogReset chan is nil, it's not used. Otherwise it can be sent to
-	// to request that the long poll activity watchdog timeout be reset.
-	onDebug func(_ context.Context, _ *tailcfg.Debug, watchdogReset chan<- struct{}) error
-
-	// onConciseNetMapSummary, if non-nil, is called with the Netmap.VeryConcise summary
-	// whenever a map response is received.
-	onConciseNetMapSummary func(string)
+	onDebug func(context.Context, *tailcfg.Debug) error
 
 	// onSelfNodeChanged is called before the NetmapUpdater if the self node was
 	// changed.
 	onSelfNodeChanged func(*netmap.NetworkMap)
 
 	// Fields storing state over the course of multiple MapResponses.
+	lastPrintMap           time.Time
 	lastNode               tailcfg.NodeView
 	peers                  map[tailcfg.NodeID]*tailcfg.NodeView // pointer to view (oddly). same pointers as sortedPeers.
 	sortedPeers            []*tailcfg.NodeView                  // same pointers as peers, but sorted by Node.ID
@@ -105,54 +101,34 @@ func newMapSession(privateNodeKey key.NodePrivate, nu NetmapUpdater, controlKnob
 		publicNodeKey:   privateNodeKey.Public(),
 		lastDNSConfig:   new(tailcfg.DNSConfig),
 		lastUserProfile: map[tailcfg.UserID]tailcfg.UserProfile{},
-		watchdogReset:   make(chan struct{}),
 
 		// Non-nil no-op defaults, to be optionally overridden by the caller.
-		logf:                   logger.Discard,
-		vlogf:                  logger.Discard,
-		cancel:                 func() {},
-		onDebug:                func(context.Context, *tailcfg.Debug, chan<- struct{}) error { return nil },
-		onConciseNetMapSummary: func(string) {},
-		onSelfNodeChanged:      func(*netmap.NetworkMap) {},
+		logf:              logger.Discard,
+		vlogf:             logger.Discard,
+		cancel:            func() {},
+		onDebug:           func(context.Context, *tailcfg.Debug) error { return nil },
+		onSelfNodeChanged: func(*netmap.NetworkMap) {},
 	}
 	ms.sessionAliveCtx, ms.sessionAliveCtxClose = context.WithCancel(context.Background())
 	return ms
 }
 
-func (ms *mapSession) clock() tstime.Clock {
-	return cmpx.Or[tstime.Clock](ms.altClock, tstime.StdClock{})
+// occasionallyPrintSummary logs summary at most once very 5 minutes. The
+// summary is the Netmap.VeryConcise result from the last received map response.
+func (ms *mapSession) occasionallyPrintSummary(summary string) {
+	// Occasionally print the netmap header.
+	// This is handy for debugging, and our logs processing
+	// pipeline depends on it. (TODO: Remove this dependency.)
+	now := ms.clock().Now()
+	if now.Sub(ms.lastPrintMap) < 5*time.Minute {
+		return
+	}
+	ms.lastPrintMap = now
+	ms.logf("[v1] new network map (periodic):\n%s", summary)
 }
 
-// StartWatchdog starts the session's watchdog timer.
-// If there's no activity in too long, it tears down the connection.
-// Call Close to release these resources.
-func (ms *mapSession) StartWatchdog() {
-	timer, timedOutChan := ms.clock().NewTimer(watchdogTimeout)
-	go func() {
-		defer timer.Stop()
-		for {
-			select {
-			case <-ms.sessionAliveCtx.Done():
-				ms.vlogf("netmap: ending timeout goroutine")
-				return
-			case <-timedOutChan:
-				ms.logf("map response long-poll timed out!")
-				ms.cancel()
-				return
-			case <-ms.watchdogReset:
-				if !timer.Stop() {
-					select {
-					case <-timedOutChan:
-					case <-ms.sessionAliveCtx.Done():
-						ms.vlogf("netmap: ending timeout goroutine")
-						return
-					}
-				}
-				ms.vlogf("netmap: reset timeout timer")
-				timer.Reset(watchdogTimeout)
-			}
-		}
-	}()
+func (ms *mapSession) clock() tstime.Clock {
+	return cmpx.Or[tstime.Clock](ms.altClock, tstime.StdClock{})
 }
 
 func (ms *mapSession) Close() {
@@ -169,7 +145,7 @@ func (ms *mapSession) Close() {
 // is [re]factoring progress enough.
 func (ms *mapSession) HandleNonKeepAliveMapResponse(ctx context.Context, resp *tailcfg.MapResponse) error {
 	if debug := resp.Debug; debug != nil {
-		if err := ms.onDebug(ctx, debug, ms.watchdogReset); err != nil {
+		if err := ms.onDebug(ctx, debug); err != nil {
 			return err
 		}
 	}
@@ -200,7 +176,7 @@ func (ms *mapSession) HandleNonKeepAliveMapResponse(ctx context.Context, resp *t
 	ms.updateStateFromResponse(resp)
 
 	if ms.tryHandleIncrementally(resp) {
-		ms.onConciseNetMapSummary(ms.lastNetmapSummary) // every 5s log
+		ms.occasionallyPrintSummary(ms.lastNetmapSummary)
 		return nil
 	}
 
@@ -210,7 +186,7 @@ func (ms *mapSession) HandleNonKeepAliveMapResponse(ctx context.Context, resp *t
 
 	nm := ms.netmap()
 	ms.lastNetmapSummary = nm.VeryConcise()
-	ms.onConciseNetMapSummary(ms.lastNetmapSummary)
+	ms.occasionallyPrintSummary(ms.lastNetmapSummary)
 
 	// If the self node changed, we might need to update persist.
 	if resp.Node != nil {

control/controlclient/sign_supported.go

@@ -1,11 +1,9 @@
 // Copyright (c) Tailscale Inc & AUTHORS
 // SPDX-License-Identifier: BSD-3-Clause
 
-//go:build windows && cgo
+//go:build windows
 
-// darwin,cgo is also supported by certstore but machineCertificateSubject will
-// need to be loaded by a different mechanism, so this is not currently enabled
-// on darwin.
+// darwin,cgo is also supported by certstore but untested, so it is not enabled.
 
 package controlclient
 
@@ -21,7 +19,7 @@ import (
 	"github.com/tailscale/certstore"
 	"tailscale.com/tailcfg"
 	"tailscale.com/types/key"
-	"tailscale.com/util/winutil"
+	"tailscale.com/util/syspolicy"
 )
 
 var getMachineCertificateSubjectOnce struct {
@@ -40,7 +38,7 @@ var getMachineCertificateSubjectOnce struct {
 // Example: "CN=Tailscale Inc Test Root CA,OU=Tailscale Inc Test Certificate Authority,O=Tailscale Inc,ST=ON,C=CA"
 func getMachineCertificateSubject() string {
 	getMachineCertificateSubjectOnce.Do(func() {
-		getMachineCertificateSubjectOnce.v, _ = winutil.GetRegString("MachineCertificateSubject")
+		getMachineCertificateSubjectOnce.v, _ = syspolicy.GetString("MachineCertificateSubject", "")
 	})
 
 	return getMachineCertificateSubjectOnce.v

control/controlclient/sign_unsupported.go

@@ -1,7 +1,7 @@
 // Copyright (c) Tailscale Inc & AUTHORS
 // SPDX-License-Identifier: BSD-3-Clause
 
-//go:build !windows || !cgo
+//go:build !windows
 
 package controlclient
 

control/controlknobs/controlknobs.go

@@ -7,9 +7,7 @@ package controlknobs
 
 import (
 	"slices"
-	"strconv"
 	"sync/atomic"
-	"time"
 
 	"tailscale.com/syncs"
 	"tailscale.com/tailcfg"
@@ -54,10 +52,6 @@ type Knobs struct {
 	// DisableDNSForwarderTCPRetries is whether the DNS forwarder should
 	// skip retrying truncated queries over TCP.
 	DisableDNSForwarderTCPRetries atomic.Bool
-
-	// MagicsockSessionActiveTimeout is an alternate magicsock session timeout
-	// duration to use. If zero or unset, the default is used.
-	MagicsockSessionActiveTimeout syncs.AtomicValue[time.Duration]
 }
 
 // UpdateFromNodeAttributes updates k (if non-nil) based on the provided self
@@ -97,17 +91,6 @@ func (k *Knobs) UpdateFromNodeAttributes(selfNodeAttrs []tailcfg.NodeCapability,
 	k.DisableDeltaUpdates.Store(disableDeltaUpdates)
 	k.PeerMTUEnable.Store(peerMTUEnable)
 	k.DisableDNSForwarderTCPRetries.Store(dnsForwarderDisableTCPRetries)
-
-	var timeout time.Duration
-	if vv := capMap[tailcfg.NodeAttrMagicsockSessionTimeout]; len(vv) > 0 {
-		if v, _ := strconv.Unquote(string(vv[0])); v != "" {
-			timeout, _ = time.ParseDuration(v)
-			timeout = max(timeout, 0)
-		}
-	}
-	if was := k.MagicsockSessionActiveTimeout.Load(); was != timeout {
-		k.MagicsockSessionActiveTimeout.Store(timeout)
-	}
 }
 
 // AsDebugJSON returns k as something that can be marshalled with json.Marshal
@@ -126,6 +109,5 @@ func (k *Knobs) AsDebugJSON() map[string]any {
 		"DisableDeltaUpdates":           k.DisableDeltaUpdates.Load(),
 		"PeerMTUEnable":                 k.PeerMTUEnable.Load(),
 		"DisableDNSForwarderTCPRetries": k.DisableDNSForwarderTCPRetries.Load(),
-		"MagicsockSessionActiveTimeout": k.MagicsockSessionActiveTimeout.Load().String(),
 	}
 }

derp/derphttp/derphttp_client.go

@@ -56,6 +56,12 @@ type Client struct {
 	MeshKey   string             // optional; for trusted clients
 	IsProber  bool               // optional; for probers to optional declare themselves as such
 
+	// WatchConnectionChanges is whether the client wishes to subscribe to
+	// notifications about clients connecting & disconnecting.
+	//
+	// Only trusted connections (using MeshKey) are allowed to use this.
+	WatchConnectionChanges bool
+
 	// BaseContext, if non-nil, returns the base context to use for dialing a
 	// new derp server. If nil, context.Background is used.
 	// In either case, additional timeouts may be added to the base context.
@@ -80,6 +86,7 @@ type Client struct {
 	addrFamSelAtomic syncs.AtomicValue[AddressFamilySelector]
 
 	mu           sync.Mutex
+	started      bool // true upon first connect, never transitions to false
 	preferred    bool
 	canAckPings  bool
 	closed       bool
@@ -93,7 +100,7 @@ type Client struct {
 }
 
 func (c *Client) String() string {
-	return fmt.Sprintf("<derphttp_client.Client %s url=%s>", c.serverPubKey.ShortString(), c.url)
+	return fmt.Sprintf("<derphttp_client.Client %s url=%s>", c.ServerPublicKey().ShortString(), c.url)
 }
 
 // NewRegionClient returns a new DERP-over-HTTP client. It connects lazily.
@@ -142,6 +149,15 @@ func NewClient(privateKey key.NodePrivate, serverURL string, logf logger.Logf) (
 	return c, nil
 }
 
+// isStarted reports whether this client has been used yet.
+//
+// If if reports false, it may still have its exported fields configured.
+func (c *Client) isStarted() bool {
+	c.mu.Lock()
+	defer c.mu.Unlock()
+	return c.started
+}
+
 // Connect connects or reconnects to the server, unless already connected.
 // It returns nil if there was already a good connection, or if one was made.
 func (c *Client) Connect(ctx context.Context) error {
@@ -226,7 +242,7 @@ func (c *Client) useHTTPS() bool {
 // tlsServerName returns the tls.Config.ServerName value (for the TLS ClientHello).
 func (c *Client) tlsServerName(node *tailcfg.DERPNode) string {
 	if c.url != nil {
-		return c.url.Host
+		return c.url.Hostname()
 	}
 	return node.HostName
 }
@@ -284,6 +300,7 @@ func useWebsockets() bool {
 func (c *Client) connect(ctx context.Context, caller string) (client *derp.Client, connGen int, err error) {
 	c.mu.Lock()
 	defer c.mu.Unlock()
+	c.started = true
 	if c.closed {
 		return nil, 0, ErrClientClosed
 	}
@@ -495,6 +512,13 @@ func (c *Client) connect(ctx context.Context, caller string) (client *derp.Clien
 		}
 	}
 
+	if c.WatchConnectionChanges {
+		if err := derpClient.WatchConnectionChanges(); err != nil {
+			go httpConn.Close()
+			return nil, 0, err
+		}
+	}
+
 	c.serverPubKey = derpClient.ServerPublicKey()
 	c.client = derpClient
 	c.netConn = tcpConn
@@ -956,22 +980,6 @@ func (c *Client) NotePreferred(v bool) {
 	}
 }
 
-// WatchConnectionChanges sends a request to subscribe to
-// notifications about clients connecting & disconnecting.
-//
-// Only trusted connections (using MeshKey) are allowed to use this.
-func (c *Client) WatchConnectionChanges() error {
-	client, _, err := c.connect(c.newContext(), "derphttp.Client.WatchConnectionChanges")
-	if err != nil {
-		return err
-	}
-	err = client.WatchConnectionChanges()
-	if err != nil {
-		c.closeForReconnect(client)
-	}
-	return err
-}
-
 // ClosePeer asks the server to close target's TCP connection.
 //
 // Only trusted connections (using MeshKey) are allowed to use this.

derp/derphttp/derphttp_test.go

@@ -9,6 +9,7 @@ import (
 	"crypto/tls"
 	"net"
 	"net/http"
+	"net/netip"
 	"sync"
 	"testing"
 	"time"
@@ -206,3 +207,243 @@ func TestPing(t *testing.T) {
 		t.Fatalf("Ping: %v", err)
 	}
 }
+
+func newTestServer(t *testing.T, k key.NodePrivate) (serverURL string, s *derp.Server) {
+	s = derp.NewServer(k, t.Logf)
+	httpsrv := &http.Server{
+		TLSNextProto: make(map[string]func(*http.Server, *tls.Conn, http.Handler)),
+		Handler:      Handler(s),
+	}
+
+	ln, err := net.Listen("tcp4", "localhost:0")
+	if err != nil {
+		t.Fatal(err)
+	}
+	serverURL = "http://" + ln.Addr().String()
+	s.SetMeshKey("1234")
+
+	go func() {
+		if err := httpsrv.Serve(ln); err != nil {
+			if err == http.ErrServerClosed {
+				t.Logf("server closed")
+				return
+			}
+			panic(err)
+		}
+	}()
+	return
+}
+
+func newWatcherClient(t *testing.T, watcherPrivateKey key.NodePrivate, serverToWatchURL string) (c *Client) {
+	c, err := NewClient(watcherPrivateKey, serverToWatchURL, t.Logf)
+	if err != nil {
+		t.Fatal(err)
+	}
+	c.MeshKey = "1234"
+	return
+}
+
+// breakConnection breaks the connection, which should trigger a reconnect.
+func (c *Client) breakConnection(brokenClient *derp.Client) {
+	c.mu.Lock()
+	defer c.mu.Unlock()
+	if c.client != brokenClient {
+		return
+	}
+	if c.netConn != nil {
+		c.netConn.Close()
+		c.netConn = nil
+	}
+	c.client = nil
+}
+
+// Test that a watcher connection successfully reconnects and processes peer
+// updates after a different thread breaks and reconnects the connection, while
+// the watcher is waiting on recv().
+func TestBreakWatcherConnRecv(t *testing.T) {
+	// Set the wait time before a retry after connection failure to be much lower.
+	// This needs to be early in the test, for defer to run right at the end after
+	// the DERP client has finished.
+	origRetryInterval := retryInterval
+	retryInterval = 50 * time.Millisecond
+	defer func() { retryInterval = origRetryInterval }()
+
+	var wg sync.WaitGroup
+	defer wg.Wait()
+	// Make the watcher server
+	serverPrivateKey1 := key.NewNode()
+	_, s1 := newTestServer(t, serverPrivateKey1)
+	defer s1.Close()
+
+	// Make the watched server
+	serverPrivateKey2 := key.NewNode()
+	serverURL2, s2 := newTestServer(t, serverPrivateKey2)
+	defer s2.Close()
+
+	// Make the watcher (but it is not connected yet)
+	watcher1 := newWatcherClient(t, serverPrivateKey1, serverURL2)
+	defer watcher1.Close()
+
+	ctx, cancel := context.WithCancel(context.Background())
+	defer cancel()
+
+	watcherChan := make(chan int, 1)
+
+	// Start the watcher thread (which connects to the watched server)
+	wg.Add(1) // To avoid using t.Logf after the test ends. See https://golang.org/issue/40343
+	go func() {
+		defer wg.Done()
+		var peers int
+		add := func(k key.NodePublic, _ netip.AddrPort) {
+			t.Logf("add: %v", k.ShortString())
+			peers++
+			// Signal that the watcher has run
+			watcherChan <- peers
+		}
+		remove := func(k key.NodePublic) { t.Logf("remove: %v", k.ShortString()); peers-- }
+
+		watcher1.RunWatchConnectionLoop(ctx, serverPrivateKey1.Public(), t.Logf, add, remove)
+	}()
+
+	timer := time.NewTimer(5 * time.Second)
+	defer timer.Stop()
+
+	// Wait for the watcher to run, then break the connection and check if it
+	// reconnected and received peer updates.
+	for i := 0; i < 10; i++ {
+		select {
+		case peers := <-watcherChan:
+			if peers != 1 {
+				t.Fatal("wrong number of peers added during watcher connection")
+			}
+		case <-timer.C:
+			t.Fatalf("watcher did not process the peer update")
+		}
+		watcher1.breakConnection(watcher1.client)
+		// re-establish connection by sending a packet
+		watcher1.ForwardPacket(key.NodePublic{}, key.NodePublic{}, []byte("bogus"))
+
+		timer.Reset(5 * time.Second)
+	}
+}
+
+// Test that a watcher connection successfully reconnects and processes peer
+// updates after a different thread breaks and reconnects the connection, while
+// the watcher is not waiting on recv().
+func TestBreakWatcherConn(t *testing.T) {
+	// Set the wait time before a retry after connection failure to be much lower.
+	// This needs to be early in the test, for defer to run right at the end after
+	// the DERP client has finished.
+	origRetryInterval := retryInterval
+	retryInterval = 50 * time.Millisecond
+	defer func() { retryInterval = origRetryInterval }()
+
+	var wg sync.WaitGroup
+	defer wg.Wait()
+	// Make the watcher server
+	serverPrivateKey1 := key.NewNode()
+	_, s1 := newTestServer(t, serverPrivateKey1)
+	defer s1.Close()
+
+	// Make the watched server
+	serverPrivateKey2 := key.NewNode()
+	serverURL2, s2 := newTestServer(t, serverPrivateKey2)
+	defer s2.Close()
+
+	// Make the watcher (but it is not connected yet)
+	watcher1 := newWatcherClient(t, serverPrivateKey1, serverURL2)
+	defer watcher1.Close()
+
+	ctx, cancel := context.WithCancel(context.Background())
+	defer cancel()
+
+	watcherChan := make(chan int, 1)
+	breakerChan := make(chan bool, 1)
+
+	// Start the watcher thread (which connects to the watched server)
+	wg.Add(1) // To avoid using t.Logf after the test ends. See https://golang.org/issue/40343
+	go func() {
+		defer wg.Done()
+		var peers int
+		add := func(k key.NodePublic, _ netip.AddrPort) {
+			t.Logf("add: %v", k.ShortString())
+			peers++
+			// Signal that the watcher has run
+			watcherChan <- peers
+			// Wait for breaker to run
+			<-breakerChan
+		}
+		remove := func(k key.NodePublic) { t.Logf("remove: %v", k.ShortString()); peers-- }
+
+		watcher1.RunWatchConnectionLoop(ctx, serverPrivateKey1.Public(), t.Logf, add, remove)
+	}()
+
+	timer := time.NewTimer(5 * time.Second)
+	defer timer.Stop()
+
+	// Wait for the watcher to run, then break the connection and check if it
+	// reconnected and received peer updates.
+	for i := 0; i < 10; i++ {
+		select {
+		case peers := <-watcherChan:
+			if peers != 1 {
+				t.Fatal("wrong number of peers added during watcher connection")
+			}
+		case <-timer.C:
+			t.Fatalf("watcher did not process the peer update")
+		}
+		watcher1.breakConnection(watcher1.client)
+		// re-establish connection by sending a packet
+		watcher1.ForwardPacket(key.NodePublic{}, key.NodePublic{}, []byte("bogus"))
+		// signal that the breaker is done
+		breakerChan <- true
+
+		timer.Reset(5 * time.Second)
+	}
+}
+
+func noopAdd(key.NodePublic, netip.AddrPort) {}
+func noopRemove(key.NodePublic)              {}
+
+func TestRunWatchConnectionLoopServeConnect(t *testing.T) {
+	defer func() { testHookWatchLookConnectResult = nil }()
+
+	ctx, cancel := context.WithTimeout(context.Background(), 30*time.Second)
+	defer cancel()
+
+	priv := key.NewNode()
+	serverURL, s := newTestServer(t, priv)
+	defer s.Close()
+
+	pub := priv.Public()
+
+	watcher := newWatcherClient(t, priv, serverURL)
+	defer watcher.Close()
+
+	// Test connecting to ourselves, and that we get hung up on.
+	testHookWatchLookConnectResult = func(err error, wasSelfConnect bool) bool {
+		t.Helper()
+		if err != nil {
+			t.Fatalf("error connecting to server: %v", err)
+		}
+		if !wasSelfConnect {
+			t.Error("wanted self-connect; wasn't")
+		}
+		return false
+	}
+	watcher.RunWatchConnectionLoop(ctx, pub, t.Logf, noopAdd, noopRemove)
+
+	// Test connecting to the server with a zero value for ignoreServerKey,
+	// so we should always connect.
+	testHookWatchLookConnectResult = func(err error, wasSelfConnect bool) bool {
+		t.Helper()
+		if err != nil {
+			t.Fatalf("error connecting to server: %v", err)
+		}
+		if wasSelfConnect {
+			t.Error("wanted normal connect; got self connect")
+		}
+		return false
+	}
+	watcher.RunWatchConnectionLoop(ctx, key.NodePublic{}, t.Logf, noopAdd, noopRemove)
+}

derp/derphttp/mesh_client.go

@@ -14,25 +14,40 @@ import (
 	"tailscale.com/types/logger"
 )
 
-// RunWatchConnectionLoop loops until ctx is done, sending WatchConnectionChanges and subscribing to
-// connection changes.
+var retryInterval = 5 * time.Second
+
+// testHookWatchLookConnectResult, if non-nil for tests, is called by RunWatchConnectionLoop
+// with the connect result. If it returns false, the loop ends.
+var testHookWatchLookConnectResult func(connectError error, wasSelfConnect bool) (keepRunning bool)
+
+// RunWatchConnectionLoop loops until ctx is done, sending
+// WatchConnectionChanges and subscribing to connection changes.
 //
-// If the server's public key is ignoreServerKey, RunWatchConnectionLoop returns.
+// If the server's public key is ignoreServerKey, RunWatchConnectionLoop
+// returns.
 //
 // Otherwise, the add and remove funcs are called as clients come & go.
 //
-// infoLogf, if non-nil, is the logger to write periodic status
-// updates about how many peers are on the server. Error log output is
-// set to the c's logger, regardless of infoLogf's value.
+// infoLogf, if non-nil, is the logger to write periodic status updates about
+// how many peers are on the server. Error log output is set to the c's logger,
+// regardless of infoLogf's value.
 //
-// To force RunWatchConnectionLoop to return quickly, its ctx needs to
-// be closed, and c itself needs to be closed.
+// To force RunWatchConnectionLoop to return quickly, its ctx needs to be
+// closed, and c itself needs to be closed.
+//
+// It is a fatal error to call this on an already-started Client withoutq having
+// initialized Client.WatchConnectionChanges to true.
 func (c *Client) RunWatchConnectionLoop(ctx context.Context, ignoreServerKey key.NodePublic, infoLogf logger.Logf, add func(key.NodePublic, netip.AddrPort), remove func(key.NodePublic)) {
+	if !c.WatchConnectionChanges {
+		if c.isStarted() {
+			panic("invalid use of RunWatchConnectionLoop on already-started Client without setting Client.RunWatchConnectionLoop")
+		}
+		c.WatchConnectionChanges = true
+	}
 	if infoLogf == nil {
 		infoLogf = logger.Discard
 	}
 	logf := c.logf
-	const retryInterval = 5 * time.Second
 	const statusInterval = 10 * time.Second
 	var (
 		mu              sync.Mutex
@@ -101,15 +116,21 @@ func (c *Client) RunWatchConnectionLoop(ctx context.Context, ignoreServerKey key
 	}
 
 	for ctx.Err() == nil {
-		err := c.WatchConnectionChanges()
+		// Make sure we're connected before calling s.ServerPublicKey.
+		_, _, err := c.connect(ctx, "RunWatchConnectionLoop")
 		if err != nil {
-			clear()
-			logf("WatchConnectionChanges: %v", err)
+			if f := testHookWatchLookConnectResult; f != nil && !f(err, false) {
+				return
+			}
+			logf("mesh connect: %v", err)
 			sleep(retryInterval)
 			continue
 		}
-
-		if c.ServerPublicKey() == ignoreServerKey {
+		selfConnect := c.ServerPublicKey() == ignoreServerKey
+		if f := testHookWatchLookConnectResult; f != nil && !f(err, selfConnect) {
+			return
+		}
+		if selfConnect {
 			logf("detected self-connect; ignoring host")
 			return
 		}

disco/disco.go

@@ -261,7 +261,7 @@ func parsePong(ver uint8, p []byte) (m *Pong, err error) {
 func MessageSummary(m Message) string {
 	switch m := m.(type) {
 	case *Ping:
-		return fmt.Sprintf("ping tx=%x", m.TxID[:6])
+		return fmt.Sprintf("ping tx=%x padding=%v", m.TxID[:6], m.Padding)
 	case *Pong:
 		return fmt.Sprintf("pong tx=%x", m.TxID[:6])
 	case *CallMeMaybe:

docs/k8s/proxy.yaml

@@ -11,7 +11,7 @@ spec:
     # the container. The `net.ipv4.ip_forward` sysctl is not allowlisted
     # in Kubelet by default.
   - name: sysctler
-    image: busybox
+    image: "ghcr.io/tailscale/tailscale:latest"
     securityContext:
       privileged: true
     command: ["/bin/sh"]

docs/sysv/tailscale.init

@@ -0,0 +1,63 @@
+#!/bin/sh
+# Copyright (c) Tailscale Inc & AUTHORS
+# SPDX-License-Identifier: BSD-3-Clause
+
+### BEGIN INIT INFO
+# Provides:             tailscaled
+# Required-Start:
+# Required-Stop:
+# Default-Start:
+# Default-Stop:
+# Short-Description:    Tailscale Mesh Wireguard VPN
+### END INIT INFO
+
+set -e
+
+# /etc/init.d/tailscale: start and stop the Tailscale VPN service
+
+test -x /usr/sbin/tailscaled || exit 0
+
+umask 022
+
+. /lib/lsb/init-functions
+
+# Are we running from init?
+run_by_init() {
+    ([ "$previous" ] && [ "$runlevel" ]) || [ "$runlevel" = S ]
+}
+
+export PATH="${PATH:+$PATH:}/usr/sbin:/sbin"
+
+case "$1" in
+  start)
+        log_daemon_msg "Starting Tailscale VPN" "tailscaled" || true
+        if start-stop-daemon --start --oknodo --name tailscaled -m --pidfile /run/tailscaled.pid --background \
+                --exec /usr/sbin/tailscaled -- \
+                --state=/var/lib/tailscale/tailscaled.state \
+                --socket=/run/tailscale/tailscaled.sock \
+                --port 41641;
+        then
+            log_end_msg 0 || true
+        else
+            log_end_msg 1 || true
+        fi
+        ;;
+  stop)
+        log_daemon_msg "Stopping Tailscale VPN" "tailscaled" || true
+        if start-stop-daemon --stop --remove-pidfile --pidfile /run/tailscaled.pid --exec /usr/sbin/tailscaled; then
+            log_end_msg 0 || true
+        else
+            log_end_msg 1 || true
+        fi
+        ;;
+
+  status)
+        status_of_proc -p /run/tailscaled.pid /usr/sbin/tailscaled tailscaled && exit 0 || exit $?
+        ;;
+
+  *)
+        log_action_msg "Usage: /etc/init.d/tailscaled {start|stop|status}" || true
+        exit 1
+esac
+
+exit 0

flake.nix

@@ -41,14 +41,6 @@
   };
 
   outputs = { self, nixpkgs, flake-utils, flake-compat }: let
-    # Grab a helper func out of the Nix language libraries. Annoyingly
-    # these are only accessible through legacyPackages right now,
-    # which forces us to indirect through a platform-specific
-    # path. The x86_64-linux in here doesn't really matter, since all
-    # we're grabbing is a pure Nix string manipulation function that
-    # doesn't build any software.
-    fileContents = nixpkgs.legacyPackages.x86_64-linux.lib.fileContents;
-
     # tailscaleRev is the git commit at which this flake was imported,
     # or the empty string when building from a local checkout of the
     # tailscale repo.
@@ -74,17 +66,29 @@
       name = "tailscale";
 
       src = ./.;
-      vendorSha256 = fileContents ./go.mod.sri;
-      nativeBuildInputs = pkgs.lib.optionals pkgs.stdenv.isLinux [ pkgs.makeWrapper pkgs.git ];
+      vendorSha256 = pkgs.lib.fileContents ./go.mod.sri;
+      nativeBuildInputs = pkgs.lib.optionals pkgs.stdenv.isLinux [ pkgs.makeWrapper ];
       ldflags = ["-X tailscale.com/version.GitCommit=${tailscaleRev}"];
       CGO_ENABLED = 0;
       subPackages = [ "cmd/tailscale" "cmd/tailscaled" ];
       doCheck = false;
+
+      # NOTE: We strip the ${PORT} and $FLAGS because they are unset in the
+      # environment and cause issues (specifically the unset PORT). At some
+      # point, there should be a NixOS module that allows configuration of these
+      # things, but for now, we hardcode the default of port 41641 (taken from
+      # ./cmd/tailscaled/tailscaled.defaults).
       postInstall = pkgs.lib.optionalString pkgs.stdenv.isLinux ''
         wrapProgram $out/bin/tailscaled --prefix PATH : ${pkgs.lib.makeBinPath [ pkgs.iproute2 pkgs.iptables pkgs.getent pkgs.shadow ]}
         wrapProgram $out/bin/tailscale --suffix PATH : ${pkgs.lib.makeBinPath [ pkgs.procps ]}
 
-        sed -i -e "s#/usr/sbin#$out/bin#" -e "/^EnvironmentFile/d" ./cmd/tailscaled/tailscaled.service
+        sed -i \
+          -e "s#/usr/sbin#$out/bin#" \
+          -e "/^EnvironmentFile/d" \
+          -e 's/''${PORT}/41641/' \
+          -e 's/$FLAGS//' \
+          ./cmd/tailscaled/tailscaled.service
+
         install -D -m0444 -t $out/lib/systemd/system ./cmd/tailscaled/tailscaled.service
       '';
     };
@@ -97,6 +101,7 @@
       ts = tailscale pkgs;
     in {
       packages = {
+        default = ts;
         tailscale = ts;
       };
       devShell = pkgs.mkShell {
@@ -115,4 +120,4 @@
   in
     flake-utils.lib.eachDefaultSystem (system: flakeForSystem nixpkgs system);
 }
-# nix-direnv cache busting line: sha256-tCc7+umCKgOmKXbElnCmDI4ntPvvHldkxi+RwQuj9ng=
+# nix-direnv cache busting line: sha256-ynBPVRKWPcoEbbZ/atvO6VdjHVwhnWcugSD3RGJA34E=

go.mod

@@ -4,9 +4,8 @@ go 1.21
 
 require (
 	filippo.io/mkcert v1.4.4
-	github.com/Microsoft/go-winio v0.6.1
 	github.com/akutz/memconn v0.1.0
-	github.com/alexbrainman/sspi v0.0.0-20210105120005-909beea2cc74
+	github.com/alexbrainman/sspi v0.0.0-20231016080023-1a75b4708caa
 	github.com/andybalholm/brotli v1.0.5
 	github.com/anmitsu/go-shlex v0.0.0-20200514113438-38f4b401e2be
 	github.com/aws/aws-sdk-go-v2 v1.21.0
@@ -20,6 +19,7 @@ require (
 	github.com/creack/pty v1.1.18
 	github.com/dave/jennifer v1.7.0
 	github.com/dblohm7/wingoes v0.0.0-20230929194252-e994401fc077
+	github.com/digitalocean/go-smbios v0.0.0-20180907143718-390a4f403a8e
 	github.com/dsnet/try v0.0.3
 	github.com/evanw/esbuild v0.19.4
 	github.com/frankban/quicktest v1.14.5
@@ -57,7 +57,7 @@ require (
 	github.com/prometheus/client_golang v1.17.0
 	github.com/prometheus/common v0.44.0
 	github.com/skip2/go-qrcode v0.0.0-20200617195104-da1b6568686e
-	github.com/tailscale/certstore v0.1.1-0.20220316223106-78d6e1c49d8d
+	github.com/tailscale/certstore v0.1.1-0.20231020161753-77811a65f4ff
 	github.com/tailscale/depaware v0.0.0-20210622194025-720c4b409502
 	github.com/tailscale/goexpect v0.0.0-20210902213824-6e8c725cea41
 	github.com/tailscale/golang-x-crypto v0.0.0-20230713185742-f0b76a10a08e
@@ -65,8 +65,8 @@ require (
 	github.com/tailscale/hujson v0.0.0-20221223112325-20486734a56a
 	github.com/tailscale/mkctr v0.0.0-20220601142259-c0b937af2e89
 	github.com/tailscale/netlink v1.1.1-0.20211101221916-cabfb018fe85
-	github.com/tailscale/web-client-prebuilt v0.0.0-20230919211114-7bcd7bca7bc5
-	github.com/tailscale/wireguard-go v0.0.0-20230929223258-2f6748dc88e7
+	github.com/tailscale/web-client-prebuilt v0.0.0-20231103075435-8a84ac6b1db2
+	github.com/tailscale/wireguard-go v0.0.0-20231101022006-db7604d1aa90
 	github.com/tc-hib/winres v0.2.1
 	github.com/tcnksm/go-httpstat v0.2.0
 	github.com/toqueteos/webbrowser v1.2.0
@@ -76,14 +76,14 @@ require (
 	go.uber.org/zap v1.26.0
 	go4.org/mem v0.0.0-20220726221520-4f986261bf13
 	go4.org/netipx v0.0.0-20230824141953-6213f710f925
-	golang.org/x/crypto v0.13.0
+	golang.org/x/crypto v0.14.0
 	golang.org/x/exp v0.0.0-20230905200255-921286631fa9
 	golang.org/x/mod v0.12.0
-	golang.org/x/net v0.15.0
+	golang.org/x/net v0.17.0
 	golang.org/x/oauth2 v0.12.0
 	golang.org/x/sync v0.3.0
-	golang.org/x/sys v0.12.0
-	golang.org/x/term v0.12.0
+	golang.org/x/sys v0.13.0
+	golang.org/x/term v0.13.0
 	golang.org/x/time v0.3.0
 	golang.org/x/tools v0.13.0
 	golang.zx2c4.com/wintun v0.0.0-20230126152724-0fa3db229ce2
@@ -103,6 +103,7 @@ require (
 )
 
 require (
+	github.com/Microsoft/go-winio v0.6.1 // indirect
 	github.com/google/gnostic-models v0.6.9-0.20230804172637-c7be7c783f49 // indirect
 	github.com/gorilla/securecookie v1.1.1 // indirect
 )
@@ -165,7 +166,7 @@ require (
 	github.com/denis-tingaikin/go-header v0.4.3 // indirect
 	github.com/docker/cli v24.0.6+incompatible // indirect
 	github.com/docker/distribution v2.8.2+incompatible // indirect
-	github.com/docker/docker v24.0.6+incompatible // indirect
+	github.com/docker/docker v24.0.7+incompatible // indirect
 	github.com/docker/docker-credential-helpers v0.8.0 // indirect
 	github.com/emicklei/go-restful/v3 v3.11.0 // indirect
 	github.com/emirpasic/gods v1.18.1 // indirect
@@ -320,6 +321,7 @@ require (
 	github.com/stretchr/testify v1.8.4 // indirect
 	github.com/subosito/gotenv v1.4.2 // indirect
 	github.com/t-yuki/gocover-cobertura v0.0.0-20180217150009-aaee18c8195c // indirect
+	github.com/tailscale/go-winio v0.0.0-20231025203758-c4f33415bf55
 	github.com/tdakkota/asciicheck v0.2.0 // indirect
 	github.com/tetafro/godot v1.4.11 // indirect
 	github.com/timakin/bodyclose v0.0.0-20230421092635-574207250966 // indirect

go.mod.sri

@@ -1 +1 @@
-sha256-tCc7+umCKgOmKXbElnCmDI4ntPvvHldkxi+RwQuj9ng=
+sha256-ynBPVRKWPcoEbbZ/atvO6VdjHVwhnWcugSD3RGJA34E=

go.sum

@@ -93,8 +93,8 @@ github.com/alecthomas/template v0.0.0-20190718012654-fb15b899a751/go.mod h1:LOuy
 github.com/alecthomas/units v0.0.0-20151022065526-2efee857e7cf/go.mod h1:ybxpYRFXyAe+OPACYpWeL0wqObRcbAqCMya13uyzqw0=
 github.com/alecthomas/units v0.0.0-20190717042225-c3de453c63f4/go.mod h1:ybxpYRFXyAe+OPACYpWeL0wqObRcbAqCMya13uyzqw0=
 github.com/alecthomas/units v0.0.0-20190924025748-f65c72e2690d/go.mod h1:rBZYJk541a8SKzHPHnH3zbiI+7dagKZ0cgpgrD7Fyho=
-github.com/alexbrainman/sspi v0.0.0-20210105120005-909beea2cc74 h1:Kk6a4nehpJ3UuJRqlA3JxYxBZEqCeOmATOvrbT4p9RA=
-github.com/alexbrainman/sspi v0.0.0-20210105120005-909beea2cc74/go.mod h1:cEWa1LVoE5KvSD9ONXsZrj0z6KqySlCCNKHlLzbqAt4=
+github.com/alexbrainman/sspi v0.0.0-20231016080023-1a75b4708caa h1:LHTHcTQiSGT7VVbI0o4wBRNQIgn917usHWOd6VAffYI=
+github.com/alexbrainman/sspi v0.0.0-20231016080023-1a75b4708caa/go.mod h1:cEWa1LVoE5KvSD9ONXsZrj0z6KqySlCCNKHlLzbqAt4=
 github.com/alexkohler/prealloc v1.0.0 h1:Hbq0/3fJPQhNkN0dR95AVrr6R7tou91y0uHG5pOcUuw=
 github.com/alexkohler/prealloc v1.0.0/go.mod h1:VetnK3dIgFBBKmg0YnD9F9x6Icjd+9cvfHR56wJVlKE=
 github.com/alingse/asasalint v0.0.11 h1:SFwnQXJ49Kx/1GghOFz1XGqHYKp21Kq1nHad/0WQRnw=
@@ -233,12 +233,14 @@ github.com/dblohm7/wingoes v0.0.0-20230929194252-e994401fc077 h1:WphxHslVftszsr0
 github.com/dblohm7/wingoes v0.0.0-20230929194252-e994401fc077/go.mod h1:6NCrWM5jRefaG7iN0iMShPalLsljHWBh9v1zxM2f8Xs=
 github.com/denis-tingaikin/go-header v0.4.3 h1:tEaZKAlqql6SKCY++utLmkPLd6K8IBM20Ha7UVm+mtU=
 github.com/denis-tingaikin/go-header v0.4.3/go.mod h1:0wOCWuN71D5qIgE2nz9KrKmuYBAC2Mra5RassOIQ2/c=
+github.com/digitalocean/go-smbios v0.0.0-20180907143718-390a4f403a8e h1:vUmf0yezR0y7jJ5pceLHthLaYf4bA5T14B6q39S4q2Q=
+github.com/digitalocean/go-smbios v0.0.0-20180907143718-390a4f403a8e/go.mod h1:YTIHhz/QFSYnu/EhlF2SpU2Uk+32abacUYA5ZPljz1A=
 github.com/docker/cli v24.0.6+incompatible h1:fF+XCQCgJjjQNIMjzaSmiKJSCcfcXb3TWTcc7GAneOY=
 github.com/docker/cli v24.0.6+incompatible/go.mod h1:JLrzqnKDaYBop7H2jaqPtU4hHvMKP+vjCwu2uszcLI8=
 github.com/docker/distribution v2.8.2+incompatible h1:T3de5rq0dB1j30rp0sA2rER+m322EBzniBPB6ZIzuh8=
 github.com/docker/distribution v2.8.2+incompatible/go.mod h1:J2gT2udsDAN96Uj4KfcMRqY0/ypR+oyYUYmja8H+y+w=
-github.com/docker/docker v24.0.6+incompatible h1:hceabKCtUgDqPu+qm0NgsaXf28Ljf4/pWFL7xjWWDgE=
-github.com/docker/docker v24.0.6+incompatible/go.mod h1:eEKB0N0r5NX/I1kEveEz05bcu8tLC/8azJZsviup8Sk=
+github.com/docker/docker v24.0.7+incompatible h1:Wo6l37AuwP3JaMnZa226lzVXGA3F9Ig1seQen0cKYlM=
+github.com/docker/docker v24.0.7+incompatible/go.mod h1:eEKB0N0r5NX/I1kEveEz05bcu8tLC/8azJZsviup8Sk=
 github.com/docker/docker-credential-helpers v0.8.0 h1:YQFtbBQb4VrpoPxhFuzEBPQ9E16qz5SpHLS+uswaCp8=
 github.com/docker/docker-credential-helpers v0.8.0/go.mod h1:UGFXcuoQ5TxPiB54nHOZ32AWRqQdECoh/Mg0AlEYb40=
 github.com/dsnet/try v0.0.3 h1:ptR59SsrcFUYbT/FhAbKTV6iLkeD6O18qfIWRml2fqI=
@@ -862,10 +864,12 @@ github.com/subosito/gotenv v1.4.2 h1:X1TuBLAMDFbaTAChgCBLu3DU3UPyELpnF2jjJ2cz/S8
 github.com/subosito/gotenv v1.4.2/go.mod h1:ayKnFf/c6rvx/2iiLrJUk1e6plDbT3edrFNGqEflhK0=
 github.com/t-yuki/gocover-cobertura v0.0.0-20180217150009-aaee18c8195c h1:+aPplBwWcHBo6q9xrfWdMrT9o4kltkmmvpemgIjep/8=
 github.com/t-yuki/gocover-cobertura v0.0.0-20180217150009-aaee18c8195c/go.mod h1:SbErYREK7xXdsRiigaQiQkI9McGRzYMvlKYaP3Nimdk=
-github.com/tailscale/certstore v0.1.1-0.20220316223106-78d6e1c49d8d h1:K3j02b5j2Iw1xoggN9B2DIEkhWGheqFOeDkdJdBrJI8=
-github.com/tailscale/certstore v0.1.1-0.20220316223106-78d6e1c49d8d/go.mod h1:2P+hpOwd53e7JMX/L4f3VXkv1G+33ES6IWZSrkIeWNs=
+github.com/tailscale/certstore v0.1.1-0.20231020161753-77811a65f4ff h1:vnxdYZUJbsSRcIcduDW3DcQqfqaiv4FUgy25q8X+vfI=
+github.com/tailscale/certstore v0.1.1-0.20231020161753-77811a65f4ff/go.mod h1:XrBNfAFN+pwoWuksbFS9Ccxnopa15zJGgXRFN90l3K4=
 github.com/tailscale/depaware v0.0.0-20210622194025-720c4b409502 h1:34icjjmqJ2HPjrSuJYEkdZ+0ItmGQAQ75cRHIiftIyE=
 github.com/tailscale/depaware v0.0.0-20210622194025-720c4b409502/go.mod h1:p9lPsd+cx33L3H9nNoecRRxPssFKUwwI50I3pZ0yT+8=
+github.com/tailscale/go-winio v0.0.0-20231025203758-c4f33415bf55 h1:Gzfnfk2TWrk8Jj4P4c1a3CtQyMaTVCznlkLZI++hok4=
+github.com/tailscale/go-winio v0.0.0-20231025203758-c4f33415bf55/go.mod h1:4k4QO+dQ3R5FofL+SanAUZe+/QfeK0+OIuwDIRu2vSg=
 github.com/tailscale/goexpect v0.0.0-20210902213824-6e8c725cea41 h1:/V2rCMMWcsjYaYO2MeovLw+ClP63OtXgCF2Y1eb8+Ns=
 github.com/tailscale/goexpect v0.0.0-20210902213824-6e8c725cea41/go.mod h1:/roCdA6gg6lQyw/Oz6gIIGu3ggJKYhF+WC/AQReE5XQ=
 github.com/tailscale/golang-x-crypto v0.0.0-20230713185742-f0b76a10a08e h1:JyeJF/HuSwvxWtsR1c0oKX1lzaSH5Wh4aX+MgiStaGQ=
@@ -878,10 +882,10 @@ github.com/tailscale/mkctr v0.0.0-20220601142259-c0b937af2e89 h1:7xU7AFQE83h0wz/
 github.com/tailscale/mkctr v0.0.0-20220601142259-c0b937af2e89/go.mod h1:OGMqrTzDqmJkGumUTtOv44Rp3/4xS+QFbE8Rn0AGlaU=
 github.com/tailscale/netlink v1.1.1-0.20211101221916-cabfb018fe85 h1:zrsUcqrG2uQSPhaUPjUQwozcRdDdSxxqhNgNZ3drZFk=
 github.com/tailscale/netlink v1.1.1-0.20211101221916-cabfb018fe85/go.mod h1:NzVQi3Mleb+qzq8VmcWpSkcSYxXIg0DkI6XDzpVkhJ0=
-github.com/tailscale/web-client-prebuilt v0.0.0-20230919211114-7bcd7bca7bc5 h1:wKUtQPRpjhZZvAuwYRMcjMZnpWSUEJWIbNJmLtDbR0k=
-github.com/tailscale/web-client-prebuilt v0.0.0-20230919211114-7bcd7bca7bc5/go.mod h1:agQPE6y6ldqCOui2gkIh7ZMztTkIQKH049tv8siLuNQ=
-github.com/tailscale/wireguard-go v0.0.0-20230929223258-2f6748dc88e7 h1:P1od5W+cX/LZZyvbKrNUXuuzxensnKEywLhxhPOeHuY=
-github.com/tailscale/wireguard-go v0.0.0-20230929223258-2f6748dc88e7/go.mod h1:BOm5fXUBFM+m9woLNBoxI9TaBXXhGNP50LX/TGIvGb4=
+github.com/tailscale/web-client-prebuilt v0.0.0-20231103075435-8a84ac6b1db2 h1:KzNItTAwrc5UmP+JpzRa8ZVNs0x/boBXleVXZq4qd/U=
+github.com/tailscale/web-client-prebuilt v0.0.0-20231103075435-8a84ac6b1db2/go.mod h1:agQPE6y6ldqCOui2gkIh7ZMztTkIQKH049tv8siLuNQ=
+github.com/tailscale/wireguard-go v0.0.0-20231101022006-db7604d1aa90 h1:lMGYrokOq9NKDw1UMBH7AsS4boZ41jcduvYaRIdedhE=
+github.com/tailscale/wireguard-go v0.0.0-20231101022006-db7604d1aa90/go.mod h1:BOm5fXUBFM+m9woLNBoxI9TaBXXhGNP50LX/TGIvGb4=
 github.com/tc-hib/winres v0.2.1 h1:YDE0FiP0VmtRaDn7+aaChp1KiF4owBiJa5l964l5ujA=
 github.com/tc-hib/winres v0.2.1/go.mod h1:C/JaNhH3KBvhNKVbvdlDWkbMDO9H4fKKDaN7/07SSuk=
 github.com/tcnksm/go-httpstat v0.2.0 h1:rP7T5e5U2HfmOBmZzGgGZjBQ5/GluWUylujl0tJ04I0=
@@ -984,8 +988,8 @@ golang.org/x/crypto v0.1.0/go.mod h1:RecgLatLF4+eUMCP1PoPZQb+cVrJcOPbHkTkbkB9sbw
 golang.org/x/crypto v0.3.0/go.mod h1:hebNnKkNXi2UzZN1eVRvBB7co0a+JxK6XbPiWVs/3J4=
 golang.org/x/crypto v0.3.1-0.20221117191849-2c476679df9a/go.mod h1:hebNnKkNXi2UzZN1eVRvBB7co0a+JxK6XbPiWVs/3J4=
 golang.org/x/crypto v0.7.0/go.mod h1:pYwdfH91IfpZVANVyUOhSIPZaFoJGxTFbZhFTx+dXZU=
-golang.org/x/crypto v0.13.0 h1:mvySKfSWJ+UKUii46M40LOvyWfN0s2U+46/jDd0e6Ck=
-golang.org/x/crypto v0.13.0/go.mod h1:y6Z2r+Rw4iayiXXAIxJIDAJ1zMW4yaTpebo8fPOliYc=
+golang.org/x/crypto v0.14.0 h1:wBqGXzWJW6m1XrIKlAH0Hs1JJ7+9KBwnIO8v66Q9cHc=
+golang.org/x/crypto v0.14.0/go.mod h1:MVFd36DqK4CsrnJYDkBA3VC4m2GkXAM0PvzMCn4JQf4=
 golang.org/x/exp v0.0.0-20190121172915-509febef88a4/go.mod h1:CJ0aWSM057203Lf6IL+f9T1iT9GByDxfZKAQTCR3kQA=
 golang.org/x/exp v0.0.0-20190306152737-a1d7652674e8/go.mod h1:CJ0aWSM057203Lf6IL+f9T1iT9GByDxfZKAQTCR3kQA=
 golang.org/x/exp v0.0.0-20190510132918-efd6b22b2522/go.mod h1:ZjyILWgesfNpC6sMxTJOJm9Kp84zZh5NQWvqDGG3Qr8=
@@ -1080,8 +1084,8 @@ golang.org/x/net v0.3.0/go.mod h1:MBQ8lrhLObU/6UmLb4fmbmk5OcyYmqtbGd/9yIeKjEE=
 golang.org/x/net v0.5.0/go.mod h1:DivGGAXEgPSlEBzxGzZI+ZLohi+xUj054jfeKui00ws=
 golang.org/x/net v0.6.0/go.mod h1:2Tu9+aMcznHK/AK1HMvgo6xiTLG5rD5rZLDS+rp2Bjs=
 golang.org/x/net v0.8.0/go.mod h1:QVkue5JL9kW//ek3r6jTKnTFis1tRmNAW2P1shuFdJc=
-golang.org/x/net v0.15.0 h1:ugBLEUaxABaB5AJqW9enI0ACdci2RUd4eP51NTBvuJ8=
-golang.org/x/net v0.15.0/go.mod h1:idbUs1IY1+zTqbi8yxTbhexhEEk5ur9LInksu6HrEpk=
+golang.org/x/net v0.17.0 h1:pVaXccu2ozPjCXewfr1S7xza/zcXTity9cCdXQYSjIM=
+golang.org/x/net v0.17.0/go.mod h1:NxSsAGuq816PNPmqtQdLE42eU2Fs7NoRIZrHJAlaCOE=
 golang.org/x/oauth2 v0.0.0-20180821212333-d2e6202438be/go.mod h1:N/0e6XlmueqKjAGxoOufVs8QHGRruUQn6yWY3a++T0U=
 golang.org/x/oauth2 v0.0.0-20190226205417-e64efc72b421/go.mod h1:gOpvHmFTYa4IltrdGE7lF6nIHvwfUNPOp7c8zoXwtLw=
 golang.org/x/oauth2 v0.0.0-20190604053449-0f29369cfe45/go.mod h1:gOpvHmFTYa4IltrdGE7lF6nIHvwfUNPOp7c8zoXwtLw=
@@ -1177,8 +1181,8 @@ golang.org/x/sys v0.4.0/go.mod h1:oPkhp1MJrh7nUepCBck5+mAzfO9JrbApNNgaTdGDITg=
 golang.org/x/sys v0.4.1-0.20230131160137-e7d7f63158de/go.mod h1:oPkhp1MJrh7nUepCBck5+mAzfO9JrbApNNgaTdGDITg=
 golang.org/x/sys v0.5.0/go.mod h1:oPkhp1MJrh7nUepCBck5+mAzfO9JrbApNNgaTdGDITg=
 golang.org/x/sys v0.6.0/go.mod h1:oPkhp1MJrh7nUepCBck5+mAzfO9JrbApNNgaTdGDITg=
-golang.org/x/sys v0.12.0 h1:CM0HF96J0hcLAwsHPJZjfdNzs0gftsLfgKt57wWHJ0o=
-golang.org/x/sys v0.12.0/go.mod h1:oPkhp1MJrh7nUepCBck5+mAzfO9JrbApNNgaTdGDITg=
+golang.org/x/sys v0.13.0 h1:Af8nKPmuFypiUBjVoU9V20FiaFXOcuZI21p0ycVYYGE=
+golang.org/x/sys v0.13.0/go.mod h1:oPkhp1MJrh7nUepCBck5+mAzfO9JrbApNNgaTdGDITg=
 golang.org/x/term v0.0.0-20201126162022-7de9c90e9dd1/go.mod h1:bj7SfCRtBDWHUb9snDiAeCFNEtKQo2Wmx5Cou7ajbmo=
 golang.org/x/term v0.0.0-20210927222741-03fcf44c2211/go.mod h1:jbD1KX2456YbFQfuXm/mYQcufACuNUgVhRMnK/tPxf8=
 golang.org/x/term v0.1.0/go.mod h1:jbD1KX2456YbFQfuXm/mYQcufACuNUgVhRMnK/tPxf8=
@@ -1187,8 +1191,8 @@ golang.org/x/term v0.3.0/go.mod h1:q750SLmJuPmVoN1blW3UFBPREJfb1KmY3vwxfr+nFDA=
 golang.org/x/term v0.4.0/go.mod h1:9P2UbLfCdcvo3p/nzKvsmas4TnlujnuoV9hGgYzW1lQ=
 golang.org/x/term v0.5.0/go.mod h1:jMB1sMXY+tzblOD4FWmEbocvup2/aLOaQEp7JmGp78k=
 golang.org/x/term v0.6.0/go.mod h1:m6U89DPEgQRMq3DNkDClhWw02AUbt2daBVO4cn4Hv9U=
-golang.org/x/term v0.12.0 h1:/ZfYdc3zq+q02Rv9vGqTeSItdzZTSNDmfTi0mBAuidU=
-golang.org/x/term v0.12.0/go.mod h1:owVbMEjm3cBLCHdkQu9b1opXd4ETQWc3BhuQGKgXgvU=
+golang.org/x/term v0.13.0 h1:bb+I9cTfFazGW51MZqBVmZy7+JEJMouUHTUSKVQLBek=
+golang.org/x/term v0.13.0/go.mod h1:LTmsnFJwVN6bCy1rVCoS+qHT1HhALEFxKncY3WNNh4U=
 golang.org/x/text v0.0.0-20170915032832-14c0d48ead0c/go.mod h1:NqM8EUOU14njkJ3fqMW+pc6Ldnwhi/IjpwHt7yyuwOQ=
 golang.org/x/text v0.3.0/go.mod h1:NqM8EUOU14njkJ3fqMW+pc6Ldnwhi/IjpwHt7yyuwOQ=
 golang.org/x/text v0.3.1-0.20180807135948-17ff2d5776d2/go.mod h1:NqM8EUOU14njkJ3fqMW+pc6Ldnwhi/IjpwHt7yyuwOQ=

go.toolchain.rev

@@ -1 +1 @@
-f242beecd311476f6e6b9fa3052e253e2301e170
+56d25cd9a2efe0eee3945518fc532ec45912ccb2

hostinfo/hostinfo.go

@@ -53,7 +53,6 @@ func New() *tailcfg.Hostinfo {
 		GoVersion:       runtime.Version(),
 		Machine:         condCall(unameMachine),
 		DeviceModel:     deviceModel(),
-		PushDeviceToken: pushDeviceToken(),
 		Cloud:           string(cloudenv.Get()),
 		NoLogsNoSupport: envknob.NoLogsNoSupport(),
 		AllowsUpdate:    envknob.AllowsRemoteUpdate(),
@@ -166,18 +165,14 @@ func GetEnvType() EnvType {
 }
 
 var (
-	pushDeviceTokenAtomic atomic.Value // of string
-	deviceModelAtomic     atomic.Value // of string
-	osVersionAtomic       atomic.Value // of string
-	desktopAtomic         atomic.Value // of opt.Bool
-	packagingType         atomic.Value // of string
-	appType               atomic.Value // of string
-	firewallMode          atomic.Value // of string
+	deviceModelAtomic atomic.Value // of string
+	osVersionAtomic   atomic.Value // of string
+	desktopAtomic     atomic.Value // of opt.Bool
+	packagingType     atomic.Value // of string
+	appType           atomic.Value // of string
+	firewallMode      atomic.Value // of string
 )
 
-// SetPushDeviceToken sets the device token for use in Hostinfo updates.
-func SetPushDeviceToken(token string) { pushDeviceTokenAtomic.Store(token) }
-
 // SetDeviceModel sets the device model for use in Hostinfo updates.
 func SetDeviceModel(model string) { deviceModelAtomic.Store(model) }
 
@@ -203,11 +198,6 @@ func deviceModel() string {
 	return s
 }
 
-func pushDeviceToken() string {
-	s, _ := pushDeviceTokenAtomic.Load().(string)
-	return s
-}
-
 // FirewallMode returns the firewall mode for the app.
 // It is empty if unset.
 func FirewallMode() string {
@@ -345,10 +335,7 @@ func inAzureAppService() bool {
 }
 
 func inAWSFargate() bool {
-	if os.Getenv("AWS_EXECUTION_ENV") == "AWS_ECS_FARGATE" {
-		return true
-	}
-	return false
+	return os.Getenv("AWS_EXECUTION_ENV") == "AWS_ECS_FARGATE"
 }
 
 func inFlyDotIo() bool {
@@ -374,10 +361,7 @@ func inKubernetes() bool {
 }
 
 func inDockerDesktop() bool {
-	if os.Getenv("TS_HOST_ENV") == "dde" {
-		return true
-	}
-	return false
+	return os.Getenv("TS_HOST_ENV") == "dde"
 }
 
 func inHomeAssistantAddOn() bool {

ipn/conf.go

@@ -0,0 +1,130 @@
+// Copyright (c) Tailscale Inc & AUTHORS
+// SPDX-License-Identifier: BSD-3-Clause
+
+package ipn
+
+import (
+	"net/netip"
+
+	"tailscale.com/tailcfg"
+	"tailscale.com/types/opt"
+	"tailscale.com/types/preftype"
+)
+
+// ConfigVAlpha is the config file format for the "alpha0" version.
+type ConfigVAlpha struct {
+	Version string   // "alpha0" for now
+	Locked  opt.Bool `json:",omitempty"` // whether the config is locked from being changed by 'tailscale set'; it defaults to true
+
+	ServerURL *string  `json:",omitempty"` // defaults to https://controlplane.tailscale.com
+	AuthKey   *string  `json:",omitempty"` // as needed if NeedsLogin. either key or path to a file (if prefixed with "file:")
+	Enabled   opt.Bool `json:",omitempty"` // wantRunning; empty string defaults to true
+
+	OperatorUser *string `json:",omitempty"` // local user name who is allowed to operate tailscaled without being root or using sudo
+	Hostname     *string `json:",omitempty"`
+
+	AcceptDNS    opt.Bool `json:"acceptDNS,omitempty"` // --accept-dns
+	AcceptRoutes opt.Bool `json:"acceptRoutes,omitempty"`
+
+	ExitNode                   *string  `json:"exitNode,omitempty"` // IP, StableID, or MagicDNS base name
+	AllowLANWhileUsingExitNode opt.Bool `json:"allowLANWhileUsingExitNode,omitempty"`
+
+	AdvertiseRoutes []netip.Prefix `json:",omitempty"`
+	DisableSNAT     opt.Bool       `json:",omitempty"`
+
+	NetfilterMode *string `json:",omitempty"` // "on", "off", "nodivert"
+
+	PostureChecking opt.Bool         `json:",omitempty"`
+	RunSSHServer    opt.Bool         `json:",omitempty"` // Tailscale SSH
+	RunWebClient    opt.Bool         `json:",omitempty"`
+	ShieldsUp       opt.Bool         `json:",omitempty"`
+	AutoUpdate      *AutoUpdatePrefs `json:",omitempty"`
+	ServeConfigTemp *ServeConfig     `json:",omitempty"` // TODO(bradfitz,maisem): make separate stable type for this
+
+	// TODO(bradfitz,maisem): future something like:
+	// Profile map[string]*Config // keyed by alice@gmail.com, corp.com (TailnetSID)
+}
+
+func (c *ConfigVAlpha) ToPrefs() (MaskedPrefs, error) {
+	var mp MaskedPrefs
+	if c == nil {
+		return mp, nil
+	}
+	mp.WantRunning = !c.Enabled.EqualBool(false)
+	mp.WantRunningSet = mp.WantRunning || c.Enabled != ""
+	if c.ServerURL != nil {
+		mp.ControlURL = *c.ServerURL
+		mp.ControlURLSet = true
+	}
+	if c.AuthKey != nil && *c.AuthKey != "" {
+		mp.LoggedOut = false
+		mp.LoggedOutSet = true
+	}
+	if c.OperatorUser != nil {
+		mp.OperatorUser = *c.OperatorUser
+		mp.OperatorUserSet = true
+	}
+	if c.Hostname != nil {
+		mp.Hostname = *c.Hostname
+		mp.HostnameSet = true
+	}
+	if c.AcceptDNS != "" {
+		mp.CorpDNS = c.AcceptDNS.EqualBool(true)
+		mp.CorpDNSSet = true
+	}
+	if c.AcceptRoutes != "" {
+		mp.RouteAll = c.AcceptRoutes.EqualBool(true)
+		mp.RouteAllSet = true
+	}
+	if c.ExitNode != nil {
+		ip, err := netip.ParseAddr(*c.ExitNode)
+		if err == nil {
+			mp.ExitNodeIP = ip
+			mp.ExitNodeIPSet = true
+		} else {
+			mp.ExitNodeID = tailcfg.StableNodeID(*c.ExitNode)
+			mp.ExitNodeIDSet = true
+		}
+	}
+	if c.AllowLANWhileUsingExitNode != "" {
+		mp.ExitNodeAllowLANAccess = c.AllowLANWhileUsingExitNode.EqualBool(true)
+		mp.ExitNodeAllowLANAccessSet = true
+	}
+	if c.AdvertiseRoutes != nil {
+		mp.AdvertiseRoutes = c.AdvertiseRoutes
+		mp.AdvertiseRoutesSet = true
+	}
+	if c.DisableSNAT != "" {
+		mp.NoSNAT = c.DisableSNAT.EqualBool(true)
+		mp.NoSNAT = true
+	}
+	if c.NetfilterMode != nil {
+		m, err := preftype.ParseNetfilterMode(*c.NetfilterMode)
+		if err != nil {
+			return mp, err
+		}
+		mp.NetfilterMode = m
+		mp.NetfilterModeSet = true
+	}
+	if c.PostureChecking != "" {
+		mp.PostureChecking = c.PostureChecking.EqualBool(true)
+		mp.PostureCheckingSet = true
+	}
+	if c.RunSSHServer != "" {
+		mp.RunSSH = c.RunSSHServer.EqualBool(true)
+		mp.RunSSHSet = true
+	}
+	if c.RunWebClient != "" {
+		mp.RunWebClient = c.RunWebClient.EqualBool(true)
+		mp.RunWebClientSet = true
+	}
+	if c.ShieldsUp != "" {
+		mp.ShieldsUp = c.ShieldsUp.EqualBool(true)
+		mp.ShieldsUpSet = true
+	}
+	if c.AutoUpdate != nil {
+		mp.AutoUpdate = *c.AutoUpdate
+		mp.AutoUpdateSet = true
+	}
+	return mp, nil
+}