Files
tailscale/cmd/derper/ipcert.go
Brad Fitzpatrick 5384d23690 cmd/derper: add opt-in support for LetsEncrypt IP address certificates
LetsEncrypt made certificates for bare IP addresses generally
available in January 2026. They require the short-lived ACME
certificate profile and are valid for about six days.

Add a new --acme-ip-certs flag. When set (with the default
--certmode=letsencrypt), connections that arrive by IP address (no
TLS SNI, or an IP address SNI matching the connection's destination
address) get a LetsEncrypt cert for that IP, obtained on demand using
the "shortlived" profile and the HTTP-01 challenge served on derper's
plaintext HTTP port. Because the certificate is requested for
whatever address the connection actually arrived on, it works for
both IPv4 and IPv6 with no per-address configuration, and a client
can never make us request a certificate for an address that isn't
ours. Connections with a DNS name in the SNI keep using the regular
autocert manager for --hostname.

autocert can't do any of this itself, as it neither orders IP address
identifiers nor serves connections without SNI, so this adds a small
dedicated cert manager using tailscale.com/tempfork/acme instead.

Clients can then connect to https://<IP> without the DERPMap CertName
pinning that self-signed certs from --certmode=manual require.

Updates tailscale/corp#45167
Updates #11776

Signed-off-by: Brad Fitzpatrick <bradfitz@tailscale.com>
Change-Id: I8e2d5b0a7c4f9e1b3d6a8c2f5e0b9d4a7c1f3e6d
2026-07-22 12:33:42 -07:00

498 lines
15 KiB
Go

// Copyright (c) Tailscale Inc & contributors
// SPDX-License-Identifier: BSD-3-Clause
package main
import (
"context"
"crypto/ecdsa"
"crypto/elliptic"
"crypto/rand"
"crypto/tls"
"crypto/x509"
"encoding/json"
"encoding/pem"
"errors"
"fmt"
"io"
"log"
"net"
"net/http"
"net/netip"
"os"
"path/filepath"
"slices"
"strings"
"sync"
"time"
"tailscale.com/atomicfile"
"tailscale.com/tailcfg"
"tailscale.com/tempfork/acme"
)
// shortlivedProfile is the ACME certificate profile required by
// LetsEncrypt for IP address certificates. Certificates issued under
// it are valid for about six days.
// See https://letsencrypt.org/docs/profiles/.
const shortlivedProfile = "shortlived"
// ipCertManager is a certProvider that obtains and renews LetsEncrypt
// TLS certificates for the server's IP addresses on demand, using the
// short-lived ACME certificate profile and the HTTP-01 challenge
// served on the derper's plaintext HTTP port.
//
// Clients connecting to an IP address usually send no SNI, so the
// requested IP address is taken from the TCP connection's local
// address. That works for however many IPv4 and IPv6 addresses the
// server has, with no configuration. Clients that do send an IP
// address in the SNI get a certificate only if it matches the
// connection's local address, so a client can never make us request a
// certificate for an address that isn't ours.
//
// Connections with a DNS name in the SNI are passed through to the
// optional next provider (the regular autocert manager for the
// --hostname certificate), if any.
type ipCertManager struct {
certDir string
email string // optional ACME account contact
client *acme.Client
next certProvider // provider for DNS hostname connections, or nil
nextTLS *tls.Config // next.TLSConfig(), or nil
mu sync.Mutex
certs map[netip.Addr]*ipCertEntry
tokens map[string]string // HTTP-01 challenge URL path => response body
}
// ipCertEntry is the issuance state for one IP address.
// All fields are guarded by ipCertManager.mu.
type ipCertEntry struct {
cert *tls.Certificate // current cert with Leaf set, or nil if not yet issued
flight chan struct{} // non-nil while an issuance is running; closed when it finishes
flightErr error // result of the last finished issuance
nextAttempt time.Time // earliest time of the next issuance attempt, after a failure
retryDelay time.Duration // backoff to apply after the next failure
}
// newIPCertManager returns an ipCertManager storing its ACME account
// key and issued certificates in certdir.
//
// If directoryURL is empty, the LetsEncrypt production directory is
// used; tests point it at a fake ACME server. If next is non-nil,
// connections with a DNS name in the SNI are served by it.
func newIPCertManager(certdir, email, directoryURL string, next certProvider) (*ipCertManager, error) {
if err := os.MkdirAll(certdir, 0700); err != nil {
return nil, err
}
accountKey, err := loadOrCreateAccountKey(filepath.Join(certdir, "acme-account.key"))
if err != nil {
return nil, fmt.Errorf("ACME account key: %w", err)
}
m := &ipCertManager{
certDir: certdir,
email: email,
client: &acme.Client{
Key: accountKey,
DirectoryURL: directoryURL,
UserAgent: "tailscale-derper",
},
next: next,
certs: make(map[netip.Addr]*ipCertEntry),
tokens: make(map[string]string),
}
if next != nil {
m.nextTLS = next.TLSConfig()
}
go m.renewLoop()
return m, nil
}
func loadOrCreateAccountKey(path string) (*ecdsa.PrivateKey, error) {
if pemBytes, err := os.ReadFile(path); err == nil {
block, _ := pem.Decode(pemBytes)
if block == nil {
return nil, fmt.Errorf("invalid PEM in %s", path)
}
return x509.ParseECPrivateKey(block.Bytes)
} else if !os.IsNotExist(err) {
return nil, err
}
key, err := ecdsa.GenerateKey(elliptic.P256(), rand.Reader)
if err != nil {
return nil, err
}
der, err := x509.MarshalECPrivateKey(key)
if err != nil {
return nil, err
}
pemBytes := pem.EncodeToMemory(&pem.Block{Type: "EC PRIVATE KEY", Bytes: der})
if err := atomicfile.WriteFile(path, pemBytes, 0600); err != nil {
return nil, err
}
return key, nil
}
// certPaths returns the cert and key file paths for ip in m.certDir.
// Colons in IPv6 addresses are replaced with dots to keep the names
// filesystem-safe.
func (m *ipCertManager) certPaths(ip netip.Addr) (crtPath, keyPath string) {
base := strings.ReplaceAll(ip.String(), ":", ".")
return filepath.Join(m.certDir, base+".crt"), filepath.Join(m.certDir, base+".key")
}
func (m *ipCertManager) TLSConfig() *tls.Config {
var conf *tls.Config
if m.nextTLS != nil {
conf = m.nextTLS.Clone()
} else {
conf = &tls.Config{
NextProtos: []string{
"http/1.1",
},
}
}
conf.GetCertificate = m.getCertificate
return conf
}
// connLocalIP returns the local (server side) IP address of the
// connection that sent the ClientHello.
func connLocalIP(hi *tls.ClientHelloInfo) (netip.Addr, bool) {
if hi.Conn == nil {
return netip.Addr{}, false
}
ta, ok := hi.Conn.LocalAddr().(*net.TCPAddr)
if !ok {
return netip.Addr{}, false
}
ip := ta.AddrPort().Addr().Unmap()
return ip, ip.IsValid()
}
func (m *ipCertManager) getCertificate(hi *tls.ClientHelloInfo) (*tls.Certificate, error) {
connIP, connIPOK := connLocalIP(hi)
if hi.ServerName != "" {
sniIP, err := netip.ParseAddr(hi.ServerName)
if err != nil {
// The SNI is a DNS name; let the hostname provider handle it.
if m.nextTLS != nil && m.nextTLS.GetCertificate != nil {
return m.nextTLS.GetCertificate(hi)
}
return nil, fmt.Errorf("no certificate for hostname %q; this server only serves IP address certificates", hi.ServerName)
}
if !connIPOK || sniIP.Unmap() != connIP {
return nil, fmt.Errorf("requested certificate for IP %v does not match the connection's IP address", sniIP)
}
}
if !connIPOK {
return nil, errors.New("unable to determine the connection's local IP address")
}
ctx := hi.Context()
if ctx == nil {
ctx = context.Background()
}
return m.certForIP(ctx, connIP)
}
// certForIP returns the current certificate for ip, obtaining one
// first if there is no unexpired certificate for it. Concurrent
// callers for the same IP share a single issuance.
func (m *ipCertManager) certForIP(ctx context.Context, ip netip.Addr) (*tls.Certificate, error) {
m.mu.Lock()
e := m.entryLocked(ip)
if e.cert != nil && time.Now().Before(e.cert.Leaf.NotAfter) {
defer m.mu.Unlock()
return clipCert(e.cert), nil
}
if e.flight == nil && time.Now().Before(e.nextAttempt) {
m.mu.Unlock()
return nil, fmt.Errorf("cert issuance for %v failed recently; next attempt no earlier than %v", ip, e.nextAttempt.Format(time.RFC3339))
}
flight := m.startFlightLocked(ip, e)
m.mu.Unlock()
select {
case <-flight:
case <-ctx.Done():
return nil, ctx.Err()
}
m.mu.Lock()
defer m.mu.Unlock()
if e.cert == nil {
return nil, e.flightErr
}
return clipCert(e.cert), nil
}
func (m *ipCertManager) entryLocked(ip netip.Addr) *ipCertEntry {
e, ok := m.certs[ip]
if !ok {
e = &ipCertEntry{}
m.certs[ip] = e
}
return e
}
// clipCert returns a shallow copy of cert with a capacity-clamped
// chain so callers can never mutate the manager's long-lived
// certificate.
func clipCert(cert *tls.Certificate) *tls.Certificate {
certCopy := *cert
certCopy.Certificate = slices.Clip(certCopy.Certificate)
return &certCopy
}
// startFlightLocked starts an issuance for ip if none is running and
// returns a channel that is closed when it finishes.
func (m *ipCertManager) startFlightLocked(ip netip.Addr, e *ipCertEntry) chan struct{} {
if e.flight != nil {
return e.flight
}
done := make(chan struct{})
e.flight = done
go func() {
err := m.issue(ip)
m.mu.Lock()
defer m.mu.Unlock()
e.flight = nil
e.flightErr = err
if err != nil {
if e.retryDelay == 0 {
e.retryDelay = time.Minute
}
e.nextAttempt = time.Now().Add(e.retryDelay)
e.retryDelay = min(e.retryDelay*2, 30*time.Minute)
log.Printf("derper: acme: getting cert for %v: %v (next attempt in %v)", ip, err, time.Until(e.nextAttempt).Round(time.Second))
} else {
e.retryDelay = 0
e.nextAttempt = time.Time{}
}
close(done)
}()
return done
}
// issue obtains a certificate for ip, preferring a still-fresh one
// cached on disk over a new ACME order.
func (m *ipCertManager) issue(ip netip.Addr) error {
ctx, cancel := context.WithTimeout(context.Background(), 3*time.Minute)
defer cancel()
if cert, err := m.loadCachedCert(ip); err == nil && !certNeedsRenewal(cert.Leaf) {
m.mu.Lock()
m.entryLocked(ip).cert = cert
m.mu.Unlock()
log.Printf("derper: acme: loaded cached cert for %v (expires %v)", ip, cert.Leaf.NotAfter)
return nil
}
return m.obtainCert(ctx, ip)
}
// loadCachedCert loads a previously issued certificate for ip from
// disk, if present and still valid.
func (m *ipCertManager) loadCachedCert(ip netip.Addr) (*tls.Certificate, error) {
crtPath, keyPath := m.certPaths(ip)
cert, err := tls.LoadX509KeyPair(crtPath, keyPath)
if err != nil {
return nil, err
}
leaf, err := x509.ParseCertificate(cert.Certificate[0])
if err != nil {
return nil, err
}
now := time.Now()
if now.Before(leaf.NotBefore) || now.After(leaf.NotAfter) {
return nil, fmt.Errorf("cached cert is expired or not yet valid (NotAfter %v)", leaf.NotAfter)
}
if err := leaf.VerifyHostname(ip.String()); err != nil {
return nil, err
}
cert.Leaf = leaf
return &cert, nil
}
// HTTPHandler returns a handler serving HTTP-01 challenge responses on
// the derper's plaintext HTTP port, sending all other requests to the
// next provider's handler, if any, and otherwise to fallback.
func (m *ipCertManager) HTTPHandler(fallback http.Handler) http.Handler {
if m.next != nil {
fallback = m.next.HTTPHandler(fallback)
}
return http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
if !strings.HasPrefix(r.URL.Path, "/.well-known/acme-challenge/") {
fallback.ServeHTTP(w, r)
return
}
m.mu.Lock()
response, ok := m.tokens[r.URL.Path]
m.mu.Unlock()
if !ok {
http.NotFound(w, r)
return
}
w.Header().Set("Content-Type", "text/plain")
io.WriteString(w, response)
})
}
func (m *ipCertManager) setToken(path, response string) {
m.mu.Lock()
defer m.mu.Unlock()
m.tokens[path] = response
}
func (m *ipCertManager) deleteToken(path string) {
m.mu.Lock()
defer m.mu.Unlock()
delete(m.tokens, path)
}
// certNeedsRenewal reports whether leaf has less than a third of its
// lifetime remaining. LetsEncrypt short-lived certs are valid for
// about six days, so renewal happens roughly every four.
func certNeedsRenewal(leaf *x509.Certificate) bool {
total := leaf.NotAfter.Sub(leaf.NotBefore)
return time.Until(leaf.NotAfter) < total/3
}
// renewLoop runs for the lifetime of the process, renewing each issued
// certificate as it approaches expiry.
func (m *ipCertManager) renewLoop() {
for {
time.Sleep(time.Hour)
m.mu.Lock()
now := time.Now()
for ip, e := range m.certs {
if e.cert != nil && certNeedsRenewal(e.cert.Leaf) && e.flight == nil && now.After(e.nextAttempt) {
m.startFlightLocked(ip, e)
}
}
m.mu.Unlock()
}
}
// obtainCert does one ACME issuance flow for ip: it registers the
// account if needed, orders a short-lived profile certificate for the
// IP address identifier, fulfills the HTTP-01 challenges, and installs
// and caches the issued certificate.
func (m *ipCertManager) obtainCert(ctx context.Context, ip netip.Addr) error {
ipStr := ip.String()
var contact []string
if m.email != "" {
contact = []string{"mailto:" + m.email}
}
_, err := m.client.Register(ctx, &acme.Account{Contact: contact}, acme.AcceptTOS)
if err != nil && !errors.Is(err, acme.ErrAccountAlreadyExists) {
return fmt.Errorf("register: %w", err)
}
order, err := m.client.AuthorizeOrder(ctx, acme.IPIDs(ipStr), acme.WithOrderProfile(shortlivedProfile))
if err != nil {
return fmt.Errorf("new order: %w", err)
}
for _, authzURL := range order.AuthzURLs {
if err := m.fulfillAuthz(ctx, authzURL); err != nil {
return err
}
}
order, err = m.client.WaitOrder(ctx, order.URI)
if err != nil {
return fmt.Errorf("waiting for order: %w", err)
}
certKey, err := ecdsa.GenerateKey(elliptic.P256(), rand.Reader)
if err != nil {
return err
}
csr, err := x509.CreateCertificateRequest(rand.Reader, &x509.CertificateRequest{
IPAddresses: []net.IP{ip.AsSlice()},
}, certKey)
if err != nil {
return err
}
der, _, err := m.client.CreateOrderCert(ctx, order.FinalizeURL, csr, true)
if err != nil {
return fmt.Errorf("finalizing order: %w", err)
}
leaf, err := x509.ParseCertificate(der[0])
if err != nil {
return fmt.Errorf("parsing issued cert: %w", err)
}
if err := leaf.VerifyHostname(ipStr); err != nil {
return fmt.Errorf("issued cert: %w", err)
}
keyDER, err := x509.MarshalECPrivateKey(certKey)
if err != nil {
return err
}
keyPEM := pem.EncodeToMemory(&pem.Block{Type: "EC PRIVATE KEY", Bytes: keyDER})
var chainPEM []byte
for _, b := range der {
chainPEM = append(chainPEM, pem.EncodeToMemory(&pem.Block{Type: "CERTIFICATE", Bytes: b})...)
}
crtPath, keyPath := m.certPaths(ip)
if err := atomicfile.WriteFile(keyPath, keyPEM, 0600); err != nil {
return err
}
if err := atomicfile.WriteFile(crtPath, chainPEM, 0644); err != nil {
return err
}
m.mu.Lock()
m.entryLocked(ip).cert = &tls.Certificate{
Certificate: der,
PrivateKey: certKey,
Leaf: leaf,
}
m.mu.Unlock()
dn := &tailcfg.DERPNode{
Name: "custom",
RegionID: 900,
HostName: ipStr,
}
dnJSON, _ := json.Marshal(dn)
log.Printf("derper: acme: got cert for %v (expires %v). Configure it in DERPMap using (https://tailscale.com/s/custom-derp):\n %s", ip, leaf.NotAfter, dnJSON)
return nil
}
// fulfillAuthz completes the HTTP-01 challenge for one authorization,
// if it is still pending.
func (m *ipCertManager) fulfillAuthz(ctx context.Context, authzURL string) error {
authz, err := m.client.GetAuthorization(ctx, authzURL)
if err != nil {
return fmt.Errorf("getting authorization: %w", err)
}
if authz.Status != acme.StatusPending {
return nil
}
var challenge *acme.Challenge
for _, c := range authz.Challenges {
if c.Type == "http-01" {
challenge = c
break
}
}
if challenge == nil {
return errors.New("authorization offers no http-01 challenge")
}
response, err := m.client.HTTP01ChallengeResponse(challenge.Token)
if err != nil {
return err
}
path := m.client.HTTP01ChallengePath(challenge.Token)
m.setToken(path, response)
defer m.deleteToken(path)
if _, err := m.client.Accept(ctx, challenge); err != nil {
return fmt.Errorf("accepting challenge: %w", err)
}
if _, err := m.client.WaitAuthorization(ctx, authz.URI); err != nil {
return fmt.Errorf("waiting for authorization: %w", err)
}
return nil
}