integration: add tailscale cert test

Every client version gets a certificate from Pebble through rfc2136 and
a TSIG-checked DNS server in the test process, then runs each serve
mode; identity headers name the requesting user.

Updates #2137
Updates #1921

flakehashes.json

@@ -1,6 +1,6 @@
 {
   "vendor": {
-    "goModSum": "sha256-mZW7/mudUF/yEjla+10vo9pTH/NGy5cpyOA7Educf9k=",
+    "goModSum": "sha256-uRy4uneBtIBymQ6tXa4e8NqFKeePPlo5vAQksLjJjZ4=",
-    "sri": "sha256-LgnMChKtW6WnmpH5dEUxiLCRppyU3Rz21RZ6Q1MedKA="
+    "sri": "sha256-D+t9VtKxtuyHYtdhxyF34wqnNpObObl7H3E/wjcXTKU="
   }
 }

go.mod

@@ -24,6 +24,7 @@ require (
 	github.com/hashicorp/golang-lru/v2 v2.0.7
 	github.com/jagottsicher/termcolor v1.0.2
 	github.com/kradalby/libdns-gigahost v0.0.0-20261014145029-4c03bc63b974
+	github.com/letsencrypt/pebble/v2 v2.10.1
 	github.com/libdns/acmedns v0.5.0
 	github.com/libdns/cloudflare v0.2.2
 	github.com/libdns/hetzner/v2 v2.0.1
@@ -173,6 +174,7 @@ require (
 	github.com/kballard/go-shellquote v0.0.0-20180428030007-95032a82bc51 // indirect
 	github.com/klauspost/compress v1.20.1 // indirect
 	github.com/kradalby/gigahost-go/client v0.0.0-20261014144355-025b38b667ed // indirect
+	github.com/letsencrypt/challtestsrv v1.4.2 // indirect
 	github.com/lib/pq v1.12.3 // indirect
 	github.com/lithammer/fuzzysearch v1.1.8 // indirect
 	github.com/mattn/go-colorable v0.1.15 // indirect

go.sum

@@ -322,6 +322,10 @@ github.com/kradalby/libdns-gigahost v0.0.0-20261014145029-4c03bc63b974/go.mod h1
 github.com/kylelemons/godebug v1.1.0 h1:RPNrshWIDI6G2gRW9EHilWtl7Z6Sb1BR0xunSBf0SNc=
 github.com/kylelemons/godebug v1.1.0/go.mod h1:9/0rRGxNHcop5bhtWyNeEfOS8JIWk580+fNqagV/RAw=
 github.com/ledongthuc/pdf v0.0.0-20220302134840-0c2507a12d80/go.mod h1:imJHygn/1yfhB7XSJJKlFZKl/J+dCPAknuiaGOshXAs=
+github.com/letsencrypt/challtestsrv v1.4.2 h1:0ON3ldMhZyWlfVNYYpFuWRTmZNnyfiL9Hh5YzC3JVwU=
+github.com/letsencrypt/challtestsrv v1.4.2/go.mod h1:GhqMqcSoeGpYd5zX5TgwA6er/1MbWzx/o7yuuVya+Wk=
+github.com/letsencrypt/pebble/v2 v2.10.1 h1:oKHx3lgN4e5Nno2LKTMrVx+b+NkDptkO9aDireiBDGE=
+github.com/letsencrypt/pebble/v2 v2.10.1/go.mod h1:KtYhQ4YTjT5MtoCZ6RTCXlbrrz6cKyXROCuTpIUDJFY=
 github.com/lib/pq v1.8.0/go.mod h1:AlVN5x4E4T544tWzH6hKfbfQvm3HdbOxrmggDNAPY9o=
 github.com/lib/pq v1.12.3 h1:tTWxr2YLKwIvK90ZXEw8GP7UFHtcbTtty8zsI+YjrfQ=
 github.com/lib/pq v1.12.3/go.mod h1:/p+8NSbOcwzAEI7wiMXFlgydTwcgTr3OSKMsD2BitpA=

integration/cert_test.go

@@ -0,0 +1,463 @@
+package integration
+
+import (
+	"crypto/ecdsa"
+	"crypto/elliptic"
+	"crypto/rand"
+	"crypto/tls"
+	"crypto/x509"
+	"crypto/x509/pkix"
+	"encoding/base64"
+	"encoding/pem"
+	"errors"
+	"fmt"
+	"log"
+	"math/big"
+	"net"
+	"net/http"
+	"os"
+	"slices"
+	"strconv"
+	"strings"
+	"sync"
+	"testing"
+	"time"
+
+	"github.com/juanfont/headscale/integration/dockertestutil"
+	"github.com/juanfont/headscale/integration/hsic"
+	"github.com/juanfont/headscale/integration/integrationutil"
+	"github.com/juanfont/headscale/integration/tsic"
+	"github.com/letsencrypt/pebble/v2/ca"
+	"github.com/letsencrypt/pebble/v2/db"
+	"github.com/letsencrypt/pebble/v2/va"
+	"github.com/letsencrypt/pebble/v2/wfe"
+	"github.com/miekg/dns"
+	"github.com/ory/dockertest/v3"
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+)
+
+var errNoSuiteAddr = errors.New("test suite has no address in the scenario network")
+
+const (
+	webserverPort = 80
+	// webserverListing is in every page tsic's web server returns.
+	webserverListing = "Directory listing"
+	// headersPort is where headersEcho listens.
+	headersPort = 8081
+	// spoofedLogin is an identity header a client claims for itself.
+	spoofedLogin = "Tailscale-User-Login: mallory@test.no"
+)
+
+// headersEcho answers every request with the request's headers.
+const headersEcho = `import sys
+from http.server import BaseHTTPRequestHandler, HTTPServer
+
+
+class Echo(BaseHTTPRequestHandler):
+    def do_GET(self):
+        self.send_response(200)
+        self.end_headers()
+        self.wfile.write(str(self.headers).encode())
+
+
+HTTPServer(("127.0.0.1", int(sys.argv[1])), Echo).serve_forever()
+`
+
+// TestTailscaleCert runs `tailscale cert` on every client version against
+// headscale's real rfc2136 provider, then runs every `tailscale serve`
+// mode on each and fetches it from another user's node. A TSIG-checked
+// DNS server and Pebble (Let's Encrypt's test CA) run inside this test
+// process; the containers reach them through the test suite's address in
+// the scenario network.
+//
+// Not parallel: Pebble reads its knobs from the environment.
+func TestTailscaleCert(t *testing.T) {
+	IntegrationSkip(t)
+
+	spec := ScenarioSpec{
+		NodesPerUser: len(MustTestVersions),
+		Users:        []string{"user1"},
+	}
+
+	scenario, err := NewScenario(spec)
+	require.NoError(t, err)
+
+	defer scenario.ShutdownAssertNoPanics(t)
+
+	suiteIP, err := suiteAddrIn(scenario.Networks()[0])
+	require.NoError(t, err)
+
+	tsigKey := base64.StdEncoding.EncodeToString([]byte("headscale-integration-tsig-key"))
+	zone := startUpdateDNS(t, "headscale.", tsigKey)
+	directoryURL, pebbleCA, issuerRoot := startPebble(t, zone, suiteIP)
+
+	err = scenario.CreateHeadscaleEnv(
+		[]tsic.Option{
+			tsic.WithCACert(pebbleCA),
+			// So curl trusts certificates Pebble issues.
+			tsic.WithCACert(issuerRoot),
+			tsic.WithPackages("curl"),
+			// Backend for the serve proxies.
+			tsic.WithWebserver(webserverPort),
+			tsic.WithExtraCommands("export TS_DEBUG_ACME_DIRECTORY_URL=" + directoryURL),
+		},
+		hsic.WithTestName("cert"),
+		hsic.WithConfigEnv(map[string]string{
+			"HEADSCALE_DNS_CERTIFICATES_ENABLED":          "true",
+			"HEADSCALE_DNS_CHALLENGE_PROVIDER_NAME":       "rfc2136",
+			"HEADSCALE_DNS_CHALLENGE_PROVIDER_SERVER":     net.JoinHostPort(suiteIP, zone.port),
+			"HEADSCALE_DNS_CHALLENGE_PROVIDER_KEY_NAME":   "headscale.",
+			"HEADSCALE_DNS_CHALLENGE_PROVIDER_KEY_ALG":    dns.HmacSHA256,
+			"HEADSCALE_DNS_CHALLENGE_PROVIDER_KEY":        tsigKey,
+			"HEADSCALE_DNS_CHALLENGE_PROPAGATION_TIMEOUT": "0s",
+		}),
+	)
+	requireNoErrHeadscaleEnv(t, err)
+
+	allClients, err := scenario.ListTailscaleClients()
+	requireNoErrListClients(t, err)
+
+	roots := x509.NewCertPool()
+	require.True(t, roots.AppendCertsFromPEM(issuerRoot))
+
+	for _, client := range allClients {
+		fqdn, err := client.FQDN()
+		require.NoError(t, err)
+
+		fqdn = strings.TrimSuffix(fqdn, ".")
+
+		assert.EventuallyWithT(t, func(c *assert.CollectT) {
+			status, err := client.Status()
+			assert.NoError(c, err)
+			assert.Contains(c, status.CertDomains, fqdn)
+		}, 30*time.Second, 500*time.Millisecond, "%s should be offered a certificate name", client.Hostname())
+
+		_, stderr, err := client.Execute(
+			[]string{"tailscale", "cert", "--cert-file", "/tmp/cert.pem", "--key-file", "/tmp/key.pem", fqdn},
+			dockertestutil.ExecuteCommandTimeout(2*time.Minute),
+		)
+		require.NoError(t, err, "tailscale cert on %s: %s", client.Hostname(), stderr)
+
+		certPEM, err := client.ReadFile("/tmp/cert.pem")
+		require.NoError(t, err)
+
+		leaf, intermediates := parseChain(t, certPEM)
+		_, err = leaf.Verify(x509.VerifyOptions{
+			DNSName:       fqdn,
+			Roots:         roots,
+			Intermediates: intermediates,
+		})
+		require.NoError(t, err, "certificate for %s", fqdn)
+	}
+
+	// serve refuses HTTPS without the https cap. With it, every serve mode
+	// works: HTTPS from text or a proxy, plain HTTP, raw TCP, and TCP behind
+	// TLS with the certificate obtained above. Proxied requests carry the
+	// identity of the user-owned node that sent them, replacing any the
+	// client sent itself. The fetcher belongs to a second user, whose
+	// display name differs from its login, so the headers must name the
+	// requester rather than the serving node's owner, and login apart from
+	// name.
+	headscale, err := scenario.Headscale()
+	require.NoError(t, err)
+
+	_, err = headscale.Execute([]string{
+		"headscale", "users", "create", "user2",
+		"--email=user2@test.no", "--display-name=User Two",
+	})
+	require.NoError(t, err)
+
+	users, err := headscale.MapUsers()
+	require.NoError(t, err)
+
+	key, err := scenario.CreatePreAuthKey(mustParseID(users["user2"].Id), false, false)
+	require.NoError(t, err)
+
+	fetcher, err := scenario.CreateTailscaleNode("head",
+		tsic.WithNetwork(scenario.Networks()[0]),
+		tsic.WithCACert(issuerRoot),
+		tsic.WithPackages("curl"),
+	)
+	require.NoError(t, err)
+
+	scenario.GetOrCreateUser("user2").Clients[fetcher.Hostname()] = fetcher
+
+	require.NoError(t, fetcher.Login(headscale.GetEndpoint(), key.Key))
+	require.NoError(t, fetcher.WaitForRunning(integrationutil.PeerSyncTimeout()))
+
+	backend := fmt.Sprintf("127.0.0.1:%d", webserverPort)
+	headersBackend := fmt.Sprintf("127.0.0.1:%d", headersPort)
+
+	for _, client := range allClients {
+		fqdn, err := client.FQDN()
+		require.NoError(t, err)
+
+		fqdn = strings.TrimSuffix(fqdn, ".")
+
+		require.NoError(t, client.WriteFile("/tmp/headers.py", []byte(headersEcho)))
+		_, stderr, err := client.Execute([]string{
+			"sh", "-c", fmt.Sprintf("python3 /tmp/headers.py %d >/dev/null 2>&1 &", headersPort),
+		})
+		require.NoError(t, err, "starting headers echo on %s: %s", client.Hostname(), stderr)
+
+		for _, args := range [][]string{
+			{"text:" + client.Hostname()},
+			{"--https=8443", "http://" + backend},
+			{"--http=8080", "text:" + client.Hostname()},
+			{"--tcp=2222", "tcp://" + backend},
+			{"--tls-terminated-tcp=9443", "tcp://" + backend},
+			{"--https=8444", "http://" + headersBackend},
+		} {
+			_, stderr, err := client.Execute(append([]string{"tailscale", "serve", "--bg", "--yes"}, args...))
+			require.NoError(t, err, "tailscale serve %v on %s: %s", args, client.Hostname(), stderr)
+		}
+
+		for url, wants := range map[string][]string{
+			"https://" + fqdn:           {client.Hostname()},
+			"https://" + fqdn + ":8443": {webserverListing},
+			"http://" + fqdn + ":8080":  {client.Hostname()},
+			"http://" + fqdn + ":2222":  {webserverListing},
+			"https://" + fqdn + ":9443": {webserverListing},
+			"https://" + fqdn + ":8444": {
+				"Tailscale-User-Login: user2@test.no",
+				"Tailscale-User-Name: User Two",
+			},
+		} {
+			assert.EventuallyWithT(t, func(c *assert.CollectT) {
+				body, _, err := fetcher.Execute([]string{
+					"curl", "--silent", "--fail", "--max-time", "10",
+					"--header", spoofedLogin,
+					"--connect-to", fqdn + "::" + client.MustIPv4().String() + ":", url,
+				}, dockertestutil.ExecuteCommandTimeout(20*time.Second))
+				assert.NoError(c, err)
+
+				for _, want := range wants {
+					assert.Contains(c, body, want)
+				}
+
+				assert.NotContains(c, body, spoofedLogin)
+			}, 60*time.Second, time.Second, "%s should be served", url)
+		}
+	}
+}
+
+// suiteAddrIn returns this test process's address in network, which the
+// containers on that network can reach.
+func suiteAddrIn(network *dockertest.Network) (string, error) {
+	addrs, err := net.InterfaceAddrs()
+	if err != nil {
+		return "", err
+	}
+
+	for _, cfg := range network.Network.IPAM.Config {
+		_, subnet, err := net.ParseCIDR(cfg.Subnet)
+		if err != nil {
+			continue
+		}
+
+		for _, addr := range addrs {
+			if ipnet, ok := addr.(*net.IPNet); ok && subnet.Contains(ipnet.IP) {
+				return ipnet.IP.String(), nil
+			}
+		}
+	}
+
+	return "", errNoSuiteAddr
+}
+
+// updateDNS is an authoritative DNS server for one zone that accepts
+// RFC 2136 updates signed with a TSIG key, like a BIND zone with an
+// update-policy, so an issued certificate proves headscale signs them. It
+// serves TCP only: both rfc2136 and Pebble use TCP.
+type updateDNS struct {
+	addr, port string
+
+	mu  sync.Mutex
+	txt map[string][]string
+}
+
+func startUpdateDNS(t *testing.T, keyName, key string) *updateDNS {
+	t.Helper()
+
+	ln, err := net.Listen("tcp", ":0") //nolint:noctx,gosec // containers must reach it
+	require.NoError(t, err)
+
+	_, port, err := net.SplitHostPort(ln.Addr().String())
+	require.NoError(t, err)
+
+	z := &updateDNS{addr: net.JoinHostPort("127.0.0.1", port), port: port, txt: map[string][]string{}}
+	srv := &dns.Server{
+		Listener:   ln,
+		TsigSecret: map[string]string{keyName: key},
+		Handler:    z,
+		// The default rejects UPDATE as not implemented.
+		MsgAcceptFunc: func(dns.Header) dns.MsgAcceptAction { return dns.MsgAccept },
+	}
+
+	go func() { _ = srv.ActivateAndServe() }()
+
+	t.Cleanup(func() { _ = srv.Shutdown() })
+
+	return z
+}
+
+func (z *updateDNS) ServeDNS(w dns.ResponseWriter, r *dns.Msg) {
+	m := new(dns.Msg)
+	m.SetReply(r)
+	m.Authoritative = true
+
+	z.mu.Lock()
+	defer z.mu.Unlock()
+
+	if r.Opcode == dns.OpcodeUpdate {
+		if r.IsTsig() == nil || w.TsigStatus() != nil {
+			m.Rcode = dns.RcodeRefused
+		} else {
+			for _, rr := range r.Ns {
+				txt, ok := rr.(*dns.TXT)
+				if !ok {
+					continue
+				}
+
+				name := strings.ToLower(txt.Hdr.Name)
+				value := strings.Join(txt.Txt, "")
+
+				switch txt.Hdr.Class {
+				case dns.ClassINET:
+					z.txt[name] = append(z.txt[name], value)
+				case dns.ClassNONE:
+					z.txt[name] = slices.DeleteFunc(z.txt[name], func(v string) bool { return v == value })
+				}
+			}
+
+			// rfc2136 rejects an unsigned reply to a signed update.
+			tsig := r.IsTsig()
+			m.SetTsig(tsig.Hdr.Name, tsig.Algorithm, 300, time.Now().Unix())
+		}
+
+		_ = w.WriteMsg(m)
+
+		return
+	}
+
+	for _, q := range r.Question {
+		if q.Qtype != dns.TypeTXT {
+			continue
+		}
+
+		for _, v := range z.txt[strings.ToLower(q.Name)] {
+			m.Answer = append(m.Answer, &dns.TXT{
+				Hdr: dns.RR_Header{Name: q.Name, Rrtype: dns.TypeTXT, Class: dns.ClassINET, Ttl: 60},
+				Txt: []string{v},
+			})
+		}
+	}
+
+	_ = w.WriteMsg(m)
+}
+
+// startPebble runs Pebble, validating DNS-01 challenges against resolver,
+// and returns its ACME directory URL as the containers see it, the
+// certificate they must trust to reach it, and the root of the
+// certificates it issues. Pebble only accepts requests signed for an
+// https URL, so it cannot run over plain HTTP.
+func startPebble(t *testing.T, resolver *updateDNS, suiteIP string) (string, []byte, []byte) {
+	t.Helper()
+
+	// Validate at once and deterministically: no random delay, no
+	// rejected nonces, no authorization reuse across orders.
+	t.Setenv("PEBBLE_VA_NOSLEEP", "1")
+	t.Setenv("PEBBLE_WFE_NONCEREJECT", "0")
+	t.Setenv("PEBBLE_AUTHZREUSE", "0")
+
+	logger := log.New(os.Stderr, "pebble ", log.LstdFlags)
+	store := db.NewMemoryStore()
+	authority := ca.New(logger, store, "", "ecdsa", 0, 1, map[string]ca.Profile{
+		"default": {Description: "default"},
+	})
+	validator := va.New(logger, 0, 0, false, resolver.addr, store)
+	acme := wfe.New(logger, store, validator, authority, []string{"pebble.letsencrypt.org"}, false, false, 0, 0)
+
+	ln, err := net.Listen("tcp", ":0") //nolint:noctx,gosec // containers must reach it
+	require.NoError(t, err)
+
+	cert, certPEM := selfSignedCert(t, suiteIP)
+	srv := &http.Server{
+		Handler:           withFinalizeLocation(acme.Handler()),
+		ReadHeaderTimeout: 10 * time.Second,
+		TLSConfig:         &tls.Config{Certificates: []tls.Certificate{cert}, MinVersion: tls.VersionTLS12},
+	}
+
+	go func() { _ = srv.ServeTLS(ln, "", "") }()
+
+	t.Cleanup(func() { _ = srv.Close() })
+
+	port := strconv.Itoa(ln.Addr().(*net.TCPAddr).Port) //nolint:forcetypeassert // tcp listener
+
+	issuerRoot := pem.EncodeToMemory(&pem.Block{Type: "CERTIFICATE", Bytes: authority.GetRootCert(0).DER})
+
+	return "https://" + net.JoinHostPort(suiteIP, port) + wfe.DirectoryPath, certPEM, issuerRoot
+}
+
+// withFinalizeLocation adds the order URL as Location to finalize replies.
+// The Tailscale client polls the order at that URL until the certificate
+// is issued; Let's Encrypt sends it, Pebble does not.
+func withFinalizeLocation(next http.Handler) http.Handler {
+	return http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		if id, ok := strings.CutPrefix(r.URL.Path, "/finalize-order/"); ok {
+			w.Header().Set("Location", "https://"+r.Host+"/my-order/"+id)
+		}
+
+		next.ServeHTTP(w, r)
+	})
+}
+
+// selfSignedCert returns a certificate for ip that is its own CA.
+func selfSignedCert(t *testing.T, ip string) (tls.Certificate, []byte) {
+	t.Helper()
+
+	key, err := ecdsa.GenerateKey(elliptic.P256(), rand.Reader)
+	require.NoError(t, err)
+
+	tmpl := &x509.Certificate{
+		SerialNumber:          big.NewInt(1),
+		Subject:               pkix.Name{CommonName: "pebble"},
+		IPAddresses:           []net.IP{net.ParseIP(ip)},
+		NotBefore:             time.Now().Add(-time.Hour),
+		NotAfter:              time.Now().Add(24 * time.Hour),
+		IsCA:                  true,
+		BasicConstraintsValid: true,
+		KeyUsage:              x509.KeyUsageDigitalSignature | x509.KeyUsageCertSign,
+		ExtKeyUsage:           []x509.ExtKeyUsage{x509.ExtKeyUsageServerAuth},
+	}
+
+	der, err := x509.CreateCertificate(rand.Reader, tmpl, tmpl, &key.PublicKey, key)
+	require.NoError(t, err)
+
+	return tls.Certificate{Certificate: [][]byte{der}, PrivateKey: key},
+		pem.EncodeToMemory(&pem.Block{Type: "CERTIFICATE", Bytes: der})
+}
+
+// parseChain returns the leaf of a PEM chain and a pool of the rest.
+func parseChain(t *testing.T, chainPEM []byte) (*x509.Certificate, *x509.CertPool) {
+	t.Helper()
+
+	var certs []*x509.Certificate
+
+	for block, rest := pem.Decode(chainPEM); block != nil; block, rest = pem.Decode(rest) {
+		cert, err := x509.ParseCertificate(block.Bytes)
+		require.NoError(t, err)
+
+		certs = append(certs, cert)
+	}
+
+	require.NotEmpty(t, certs, "no certificate in PEM")
+
+	intermediates := x509.NewCertPool()
+	for _, c := range certs[1:] {
+		intermediates.AddCert(c)
+	}
+
+	return certs[0], intermediates
+}

integration/tailscale.go

@@ -56,6 +56,7 @@ type TailscaleClient interface {
 	ContainerID() string
 	MustID() types.NodeID
 	ReadFile(path string) ([]byte, error)
+	WriteFile(path string, data []byte) error
 	PacketFilter() ([]filter.Match, error)
 	ConnectToNetwork(network *dockertest.Network) error
 	DisconnectFromNetwork(network *dockertest.Network) error