ipn/ipnlocal/serve: add grant headers

Updates tailscale/corp/#28372

Signed-off-by: Gesa Stupperich <gesa@tailscale.com>

cmd/tailscale/cli/serve_legacy.go

@@ -162,20 +162,20 @@ type serveEnv struct {
 	json bool // output JSON (status only for now)
 
 	// v2 specific flags
-	bg               bgBoolFlag          // background mode
-	setPath          string              // serve path
-	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
-	service          tailcfg.ServiceName // service name
-	tun              bool                // redirect traffic to OS for service
-	allServices      bool                // apply config file to all services
+	bg               bgBoolFlag               // background mode
+	setPath          string                   // serve path
+	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
+	service          tailcfg.ServiceName      // service name
+	tun              bool                     // redirect traffic to OS for service
+	allServices      bool                     // apply config file to all services
+	userCaps         []tailcfg.PeerCapability // user capabilities to forward
 
 	lc localServeClient // localClient interface, specific to serve
-
 	// optional stuff for tests:
 	testFlagOut io.Writer
 	testStdout  io.Writer

cmd/tailscale/cli/serve_v2.go

@@ -96,6 +96,28 @@ func (b *bgBoolFlag) String() string {
 	return strconv.FormatBool(b.Value)
 }
 
+type userCapsFlag struct {
+	Value *[]tailcfg.PeerCapability
+}
+
+// Set appends s to the list of userCaps.
+func (u *userCapsFlag) Set(s string) error {
+	if s == "" {
+		return nil
+	}
+	*u.Value = append(*u.Value, tailcfg.PeerCapability(s))
+	return nil
+}
+
+// String returns the string representation of the userCaps slice.
+func (u *userCapsFlag) String() string {
+	s := make([]string, len(*u.Value))
+	for i, v := range *u.Value {
+		s[i] = string(v)
+	}
+	return strings.Join(s, ",")
+}
+
 var serveHelpCommon = strings.TrimSpace(`
 <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),
@@ -199,6 +221,7 @@ func newServeV2Command(e *serveEnv, subcmd serveMode) *ffcli.Command {
 			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.Var(&userCapsFlag{Value: &e.userCaps}, "usercaps", "User capability to forward to the server (can be specified multiple times)")
 			}
 			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")
@@ -469,7 +492,7 @@ func (e *serveEnv) runServeCombined(subcmd serveMode) execFunc {
 			if len(args) > 0 {
 				target = args[0]
 			}
-			err = e.setServe(sc, dnsName, srvType, srvPort, mount, target, funnel, magicDNSSuffix)
+			err = e.setServe(sc, dnsName, srvType, srvPort, mount, target, funnel, magicDNSSuffix, e.userCaps)
 			msg = e.messageForPort(sc, st, dnsName, srvType, srvPort)
 		}
 		if err != nil {
@@ -790,7 +813,7 @@ func (e *serveEnv) runServeSetConfig(ctx context.Context, args []string) (err er
 	for name, details := range scf.Services {
 		for ppr, ep := range details.Endpoints {
 			if ep.Protocol == conffile.ProtoTUN {
-				err := e.setServe(sc, name.String(), serveTypeTUN, 0, "", "", false, magicDNSSuffix)
+				err := e.setServe(sc, name.String(), serveTypeTUN, 0, "", "", false, magicDNSSuffix, nil)
 				if err != nil {
 					return err
 				}
@@ -812,7 +835,7 @@ func (e *serveEnv) runServeSetConfig(ctx context.Context, args []string) (err er
 					portStr := fmt.Sprint(destPort)
 					target = fmt.Sprintf("%s://%s", ep.Protocol, net.JoinHostPort(ep.Destination, portStr))
 				}
-				err := e.setServe(sc, name.String(), serveType, port, "/", target, false, magicDNSSuffix)
+				err := e.setServe(sc, name.String(), serveType, port, "/", target, false, magicDNSSuffix, nil)
 				if err != nil {
 					return fmt.Errorf("service %q: %w", name, err)
 				}
@@ -915,12 +938,12 @@ func serveFromPortHandler(tcp *ipn.TCPPortHandler) serveType {
 	}
 }
 
-func (e *serveEnv) setServe(sc *ipn.ServeConfig, dnsName string, srvType serveType, srvPort uint16, mount string, target string, allowFunnel bool, mds string) error {
+func (e *serveEnv) setServe(sc *ipn.ServeConfig, dnsName string, srvType serveType, srvPort uint16, mount string, target string, allowFunnel bool, mds string, caps []tailcfg.PeerCapability) error {
 	// update serve config based on the type
 	switch srvType {
 	case serveTypeHTTPS, serveTypeHTTP:
 		useTLS := srvType == serveTypeHTTPS
-		err := e.applyWebServe(sc, dnsName, srvPort, useTLS, mount, target, mds)
+		err := e.applyWebServe(sc, dnsName, srvPort, useTLS, mount, target, mds, caps)
 		if err != nil {
 			return fmt.Errorf("failed apply web serve: %w", err)
 		}
@@ -1084,7 +1107,7 @@ func (e *serveEnv) messageForPort(sc *ipn.ServeConfig, st *ipnstate.Status, dnsN
 	return output.String()
 }
 
-func (e *serveEnv) applyWebServe(sc *ipn.ServeConfig, dnsName string, srvPort uint16, useTLS bool, mount, target string, mds string) error {
+func (e *serveEnv) applyWebServe(sc *ipn.ServeConfig, dnsName string, srvPort uint16, useTLS bool, mount, target, mds string, caps []tailcfg.PeerCapability) error {
 	h := new(ipn.HTTPHandler)
 	switch {
 	case strings.HasPrefix(target, "text:"):
@@ -1118,6 +1141,7 @@ func (e *serveEnv) applyWebServe(sc *ipn.ServeConfig, dnsName string, srvPort ui
 			return err
 		}
 		h.Proxy = t
+		h.UserCaps = caps
 	}
 
 	// TODO: validation needs to check nested foreground configs

cmd/tailscale/cli/serve_v2_test.go

@@ -857,6 +857,53 @@ func TestServeDevConfigMutations(t *testing.T) {
 				wantErr: anyErr(),
 			}},
 		},
+		{
+			name: "forward_grant_header",
+			steps: []step{
+				{
+					command: cmd("serve --bg --usercaps=example.com/cap/foo 3000"),
+					want: &ipn.ServeConfig{
+						TCP: map[uint16]*ipn.TCPPortHandler{443: {HTTPS: true}},
+						Web: map[ipn.HostPort]*ipn.WebServerConfig{
+							"foo.test.ts.net:443": {Handlers: map[string]*ipn.HTTPHandler{
+								"/": {
+									Proxy:    "http://127.0.0.1:3000",
+									UserCaps: []tailcfg.PeerCapability{"example.com/cap/foo"},
+								},
+							}},
+						},
+					},
+				},
+				{
+					command: cmd("serve --bg --usercaps=example.com/cap/foo --usercaps=example.com/cap/bar 3000"),
+					want: &ipn.ServeConfig{
+						TCP: map[uint16]*ipn.TCPPortHandler{443: {HTTPS: true}},
+						Web: map[ipn.HostPort]*ipn.WebServerConfig{
+							"foo.test.ts.net:443": {Handlers: map[string]*ipn.HTTPHandler{
+								"/": {
+									Proxy:    "http://127.0.0.1:3000",
+									UserCaps: []tailcfg.PeerCapability{"example.com/cap/foo", "example.com/cap/bar"},
+								},
+							}},
+						},
+					},
+				},
+				{
+					command: cmd("serve --bg --usercaps=example.com/cap/bar 3000"),
+					want: &ipn.ServeConfig{
+						TCP: map[uint16]*ipn.TCPPortHandler{443: {HTTPS: true}},
+						Web: map[ipn.HostPort]*ipn.WebServerConfig{
+							"foo.test.ts.net:443": {Handlers: map[string]*ipn.HTTPHandler{
+								"/": {
+									Proxy:    "http://127.0.0.1:3000",
+									UserCaps: []tailcfg.PeerCapability{"example.com/cap/bar"},
+								},
+							}},
+						},
+					},
+				},
+			},
+		},
 	}
 
 	for _, group := range groups {
@@ -2009,7 +2056,7 @@ func TestSetServe(t *testing.T) {
 	}
 	for _, tt := range tests {
 		t.Run(tt.name, func(t *testing.T) {
-			err := e.setServe(tt.cfg, tt.dnsName, tt.srvType, tt.srvPort, tt.mountPath, tt.target, tt.allowFunnel, magicDNSSuffix)
+			err := e.setServe(tt.cfg, tt.dnsName, tt.srvType, tt.srvPort, tt.mountPath, tt.target, tt.allowFunnel, magicDNSSuffix, nil)
 			if err != nil && !tt.expectErr {
 				t.Fatalf("got error: %v; did not expect error.", err)
 			}

ipn/ipn_clone.go

@@ -232,14 +232,16 @@ func (src *HTTPHandler) Clone() *HTTPHandler {
 	}
 	dst := new(HTTPHandler)
 	*dst = *src
+	dst.UserCaps = append(src.UserCaps[:0:0], src.UserCaps...)
 	return dst
 }
 
 // A compilation failure here means this code must be regenerated, with the command at the top of this file.
 var _HTTPHandlerCloneNeedsRegeneration = HTTPHandler(struct {
-	Path  string
-	Proxy string
-	Text  string
+	Path     string
+	Proxy    string
+	Text     string
+	UserCaps []tailcfg.PeerCapability
 }{})
 
 // Clone makes a deep copy of WebServerConfig.
@@ -256,7 +258,7 @@ func (src *WebServerConfig) Clone() *WebServerConfig {
 			if v == nil {
 				dst.Handlers[k] = nil
 			} else {
-				dst.Handlers[k] = ptr.To(*v)
+				dst.Handlers[k] = v.Clone()
 			}
 		}
 	}

ipn/ipn_view.go

@@ -891,11 +891,17 @@ func (v HTTPHandlerView) Proxy() string { return v.ж.Proxy }
 // plaintext to serve (primarily for testing)
 func (v HTTPHandlerView) Text() string { return v.ж.Text }
 
+// peer capabilities to forward in grant header, e.g. example.com/cap/mon
+func (v HTTPHandlerView) UserCaps() views.Slice[tailcfg.PeerCapability] {
+	return views.SliceOf(v.ж.UserCaps)
+}
+
 // A compilation failure here means this code must be regenerated, with the command at the top of this file.
 var _HTTPHandlerViewNeedsRegeneration = HTTPHandler(struct {
-	Path  string
-	Proxy string
-	Text  string
+	Path     string
+	Proxy    string
+	Text     string
+	UserCaps []tailcfg.PeerCapability
 }{})
 
 // View returns a read-only view of WebServerConfig.

ipn/ipnlocal/serve.go

@@ -40,6 +40,7 @@ import (
 	"tailscale.com/tailcfg"
 	"tailscale.com/types/lazy"
 	"tailscale.com/types/logger"
+	"tailscale.com/types/views"
 	"tailscale.com/util/backoff"
 	"tailscale.com/util/clientmetric"
 	"tailscale.com/util/ctxkey"
@@ -64,6 +65,7 @@ func init() {
 const (
 	contentTypeHeader   = "Content-Type"
 	grpcBaseContentType = "application/grpc"
+	grantHeaderMaxSize  = 15360 // 15 KiB
 )
 
 // ErrETagMismatch signals that the given
@@ -79,7 +81,8 @@ type serveHTTPContext struct {
 	DestPort      uint16
 
 	// provides funnel-specific context, nil if not funneled
-	Funnel *funnelFlow
+	Funnel         *funnelFlow
+	PeerCapsFilter views.Slice[tailcfg.PeerCapability]
 }
 
 // funnelFlow represents a funneled connection initiated via IngressPeer
@@ -803,6 +806,7 @@ func (rp *reverseProxy) ServeHTTP(w http.ResponseWriter, r *http.Request) {
 		r.Out.Host = r.In.Host
 		addProxyForwardedHeaders(r)
 		rp.lb.addTailscaleIdentityHeaders(r)
+		rp.lb.addTailscaleGrantHeader(r)
 	}}
 
 	// There is no way to autodetect h2c as per RFC 9113
@@ -927,6 +931,62 @@ func encTailscaleHeaderValue(v string) string {
 	return mime.QEncoding.Encode("utf-8", v)
 }
 
+func (b *LocalBackend) addTailscaleGrantHeader(r *httputil.ProxyRequest) {
+	r.Out.Header.Del("Tailscale-User-Capabilities")
+
+	c, ok := serveHTTPContextKey.ValueOk(r.Out.Context())
+	if !ok || c.Funnel != nil {
+		return
+	}
+	filter := c.PeerCapsFilter
+	if filter.IsNil() {
+		return
+	}
+	peerCaps := b.PeerCaps(c.SrcAddr.Addr())
+	if peerCaps == nil {
+		return
+	}
+
+	peerCapsFiltered := make(map[tailcfg.PeerCapability][]tailcfg.RawMessage, filter.Len())
+	for _, cap := range filter.AsSlice() {
+		if peerCaps.HasCapability(cap) {
+			peerCapsFiltered[cap] = peerCaps[cap]
+		}
+	}
+
+	serialized, truncated, err := serializeUpToNBytes(peerCapsFiltered, grantHeaderMaxSize)
+	if err != nil {
+		b.logf("serve: failed to serialize PeerCapMap: %v", err)
+		return
+	}
+	if truncated {
+		b.logf("serve: serialized PeerCapMap exceeds %d bytes, forwarding truncated PeerCapMap", grantHeaderMaxSize)
+	}
+
+	r.Out.Header.Set("Tailscale-User-Capabilities", encTailscaleHeaderValue(serialized))
+}
+
+// serializeUpToNBytes serializes capMap. It arbitrarily truncates entries from the capMap
+// if the size of the serialized capMap would exceed N bytes.
+func serializeUpToNBytes(capMap tailcfg.PeerCapMap, N int) (string, bool, error) {
+	numBytes := 0
+	capped := false
+	result := tailcfg.PeerCapMap{}
+	for k, v := range capMap {
+		numBytes += len(k) + len(v)
+		if numBytes > N {
+			capped = true
+			break
+		}
+		result[k] = v
+	}
+	marshalled, err := json.Marshal(result)
+	if err != nil {
+		return "", false, err
+	}
+	return string(marshalled), capped, nil
+}
+
 // serveWebHandler is an http.HandlerFunc that maps incoming requests to the
 // correct *http.
 func (b *LocalBackend) serveWebHandler(w http.ResponseWriter, r *http.Request) {
@@ -950,6 +1010,12 @@ func (b *LocalBackend) serveWebHandler(w http.ResponseWriter, r *http.Request) {
 			http.Error(w, "unknown proxy destination", http.StatusInternalServerError)
 			return
 		}
+		// Inject user capabilities to forward into the request context
+		c, ok := serveHTTPContextKey.ValueOk(r.Context())
+		if !ok {
+			return
+		}
+		c.PeerCapsFilter = h.UserCaps()
 		h := p.(http.Handler)
 		// Trim the mount point from the URL path before proxying. (#6571)
 		if r.URL.Path != "/" {

ipn/ipnlocal/serve_test.go

@@ -16,6 +16,7 @@ import (
 	"errors"
 	"fmt"
 	"io"
+	"mime"
 	"net/http"
 	"net/http/httptest"
 	"net/netip"
@@ -27,6 +28,7 @@ import (
 	"testing"
 	"time"
 
+	"tailscale.com/control/controlclient"
 	"tailscale.com/health"
 	"tailscale.com/ipn"
 	"tailscale.com/ipn/store/mem"
@@ -41,6 +43,7 @@ import (
 	"tailscale.com/util/must"
 	"tailscale.com/util/syspolicy/policyclient"
 	"tailscale.com/wgengine"
+	"tailscale.com/wgengine/filter"
 )
 
 func TestExpandProxyArg(t *testing.T) {
@@ -768,6 +771,156 @@ func TestServeHTTPProxyHeaders(t *testing.T) {
 	}
 }
 
+func TestServeHTTPProxyGrantHeader(t *testing.T) {
+	b := newTestBackend(t)
+
+	nm := b.NetMap()
+	matches, err := filter.MatchesFromFilterRules([]tailcfg.FilterRule{
+		{
+			SrcIPs: []string{"100.150.151.152"},
+			CapGrant: []tailcfg.CapGrant{{
+				Dsts: []netip.Prefix{
+					netip.MustParsePrefix("100.150.151.151/32"),
+				},
+				CapMap: tailcfg.PeerCapMap{
+					"example.com/cap/interesting": []tailcfg.RawMessage{
+						`{"role": "🐿"}`,
+					},
+				},
+			}},
+		},
+		{
+			SrcIPs: []string{"100.150.151.153"},
+			CapGrant: []tailcfg.CapGrant{{
+				Dsts: []netip.Prefix{
+					netip.MustParsePrefix("100.150.151.151/32"),
+				},
+				CapMap: tailcfg.PeerCapMap{
+					"example.com/cap/boring": []tailcfg.RawMessage{
+						`{"role": "Viewer"}`,
+					},
+					"example.com/cap/irrelevant": []tailcfg.RawMessage{
+						`{"role": "Editor"}`,
+					},
+				},
+			}},
+		},
+	})
+	if err != nil {
+		t.Fatal(err)
+	}
+	nm.PacketFilter = matches
+	b.SetControlClientStatus(nil, controlclient.Status{NetMap: nm})
+
+	// Start test serve endpoint.
+	testServ := httptest.NewServer(http.HandlerFunc(
+		func(w http.ResponseWriter, r *http.Request) {
+			// Piping all the headers through the response writer
+			// so we can check their values in tests below.
+			for key, val := range r.Header {
+				w.Header().Add(key, strings.Join(val, ","))
+			}
+		},
+	))
+	defer testServ.Close()
+
+	conf := &ipn.ServeConfig{
+		Web: map[ipn.HostPort]*ipn.WebServerConfig{
+			"example.ts.net:443": {Handlers: map[string]*ipn.HTTPHandler{
+				"/": {
+					Proxy:    testServ.URL,
+					UserCaps: []tailcfg.PeerCapability{"example.com/cap/interesting", "example.com/cap/boring"},
+				},
+			}},
+		},
+	}
+	if err := b.SetServeConfig(conf, ""); err != nil {
+		t.Fatal(err)
+	}
+
+	type headerCheck struct {
+		header string
+		want   string
+	}
+
+	tests := []struct {
+		name        string
+		srcIP       string
+		wantHeaders []headerCheck
+	}{
+		{
+			name:  "request-from-user-within-tailnet",
+			srcIP: "100.150.151.152",
+			wantHeaders: []headerCheck{
+				{"X-Forwarded-Proto", "https"},
+				{"X-Forwarded-For", "100.150.151.152"},
+				{"Tailscale-User-Login", "someone@example.com"},
+				{"Tailscale-User-Name", "Some One"},
+				{"Tailscale-User-Profile-Pic", "https://example.com/photo.jpg"},
+				{"Tailscale-Headers-Info", "https://tailscale.com/s/serve-headers"},
+				{"Tailscale-User-Capabilities", `{"example.com/cap/interesting":[{"role":"🐿"}]}`},
+			},
+		},
+		{
+			name:  "request-from-tagged-node-within-tailnet",
+			srcIP: "100.150.151.153",
+			wantHeaders: []headerCheck{
+				{"X-Forwarded-Proto", "https"},
+				{"X-Forwarded-For", "100.150.151.153"},
+				{"Tailscale-User-Login", ""},
+				{"Tailscale-User-Name", ""},
+				{"Tailscale-User-Profile-Pic", ""},
+				{"Tailscale-Headers-Info", ""},
+				{"Tailscale-User-Capabilities", `{"example.com/cap/boring":[{"role":"Viewer"}]}`},
+			},
+		},
+		{
+			name:  "request-from-outside-tailnet",
+			srcIP: "100.160.161.162",
+			wantHeaders: []headerCheck{
+				{"X-Forwarded-Proto", "https"},
+				{"X-Forwarded-For", "100.160.161.162"},
+				{"Tailscale-User-Login", ""},
+				{"Tailscale-User-Name", ""},
+				{"Tailscale-User-Profile-Pic", ""},
+				{"Tailscale-Headers-Info", ""},
+				{"Tailscale-User-Capabilities", ""},
+			},
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			req := &http.Request{
+				URL: &url.URL{Path: "/"},
+				TLS: &tls.ConnectionState{ServerName: "example.ts.net"},
+			}
+			req = req.WithContext(serveHTTPContextKey.WithValue(req.Context(), &serveHTTPContext{
+				DestPort: 443,
+				SrcAddr:  netip.MustParseAddrPort(tt.srcIP + ":1234"), // random src port for tests
+			}))
+
+			w := httptest.NewRecorder()
+			b.serveWebHandler(w, req)
+
+			// Verify the headers. The contract with users is that identity and grant headers containing non-ASCII
+			// UTF-8 characters will be Q-encoded.
+			h := w.Result().Header
+			dec := new(mime.WordDecoder)
+			for _, c := range tt.wantHeaders {
+				maybeEncoded := h.Get(c.header)
+				got, err := dec.DecodeHeader(maybeEncoded)
+				if err != nil {
+					t.Fatalf("invalid %q header; failed to decode: %v", maybeEncoded, err)
+				}
+				if got != c.want {
+					t.Errorf("invalid %q header; want=%q, got=%q", c.header, c.want, got)
+				}
+			}
+		})
+	}
+}
+
 func Test_reverseProxyConfiguration(t *testing.T) {
 	b := newTestBackend(t)
 	type test struct {
@@ -926,6 +1079,9 @@ func newTestBackend(t *testing.T, opts ...any) *LocalBackend {
 	b.currentNode().SetNetMap(&netmap.NetworkMap{
 		SelfNode: (&tailcfg.Node{
 			Name: "example.ts.net",
+			Addresses: []netip.Prefix{
+				netip.MustParsePrefix("100.150.151.151/32"),
+			},
 		}).View(),
 		UserProfiles: map[tailcfg.UserID]tailcfg.UserProfileView{
 			tailcfg.UserID(1): (&tailcfg.UserProfile{
@@ -1171,3 +1327,89 @@ func TestServeGRPCProxy(t *testing.T) {
 		})
 	}
 }
+
+func TestSerialisePeerCapMap(t *testing.T) {
+	var tests = []struct {
+		name                string
+		capMap              tailcfg.PeerCapMap
+		maxNumBytes         int
+		wantOneOfSerialized []string
+		wantTruncated       bool
+	}{
+		{
+			name:                "empty cap map",
+			capMap:              tailcfg.PeerCapMap{},
+			maxNumBytes:         50,
+			wantOneOfSerialized: []string{"{}"},
+			wantTruncated:       false,
+		},
+		{
+			name: "cap map with one capability",
+			capMap: tailcfg.PeerCapMap{
+				"tailscale.com/cap/kubernetes": []tailcfg.RawMessage{
+					`{"impersonate": {"groups": ["tailnet-readers"]}}`,
+				},
+			},
+			maxNumBytes: 50,
+			wantOneOfSerialized: []string{
+				`{"tailscale.com/cap/kubernetes":[{"impersonate":{"groups":["tailnet-readers"]}}]}`,
+			},
+			wantTruncated: false,
+		},
+		{
+			name: "cap map with two capabilities",
+			capMap: tailcfg.PeerCapMap{
+				"foo.com/cap/something": []tailcfg.RawMessage{
+					`{"role": "Admin"}`,
+				},
+				"bar.com/cap/other-thing": []tailcfg.RawMessage{
+					`{"role": "Viewer"}`,
+				},
+			},
+			maxNumBytes: 50,
+			// Both cap map entries will be included, but they could appear in any order.
+			wantOneOfSerialized: []string{
+				`{"foo.com/cap/something":[{"role":"Admin"}],"bar.com/cap/other-thing":[{"role":"Viewer"}]}`,
+				`{"bar.com/cap/other-thing":[{"role":"Viewer"}],"foo.com/cap/something":[{"role":"Admin"}]}`,
+			},
+			wantTruncated: false,
+		},
+		{
+			name: "cap map that should be truncated to stay within size limits",
+			capMap: tailcfg.PeerCapMap{
+				"foo.com/cap/something": []tailcfg.RawMessage{
+					`{"role": "Admin"}`,
+				},
+				"bar.com/cap/other-thing": []tailcfg.RawMessage{
+					`{"role": "Viewer"}`,
+				},
+			},
+			maxNumBytes: 40,
+			// Only one cap map entry will be included, but we don't know which one.
+			wantOneOfSerialized: []string{
+				`{"foo.com/cap/something":[{"role":"Admin"}]}`,
+				`{"bar.com/cap/other-thing":[{"role":"Viewer"}]}`,
+			},
+			wantTruncated: true,
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			gotSerialized, gotCapped, err := serializeUpToNBytes(tt.capMap, tt.maxNumBytes)
+
+			if err != nil {
+				t.Fatal(err)
+			}
+			if gotCapped != tt.wantTruncated {
+				t.Errorf("got %t, want %t", gotCapped, tt.wantTruncated)
+			}
+			for _, wantSerialized := range tt.wantOneOfSerialized {
+				if gotSerialized == wantSerialized {
+					return
+				}
+			}
+			t.Errorf("want one of %v, got %q", tt.wantOneOfSerialized, gotSerialized)
+		})
+	}
+}

ipn/serve.go

@@ -160,6 +160,8 @@ type HTTPHandler struct {
 
 	Text string `json:",omitempty"` // plaintext to serve (primarily for testing)
 
+	UserCaps []tailcfg.PeerCapability `json:",omitempty"` // peer capabilities to forward in grant header, e.g. example.com/cap/mon
+
 	// TODO(bradfitz): bool to not enumerate directories? TTL on mapping for
 	// temporary ones? Error codes? Redirects?
 }