clientupdate/distsign: add new library for package signing/verification (#8943)

This library is intended for use during release to sign packages which
are then served from pkgs.tailscale.com.
The library is also then used by clients downloading packages for
`tailscale update` where OS package managers / app stores aren't used.

Updates https://github.com/tailscale/tailscale/issues/8760
Updates https://github.com/tailscale/tailscale/issues/6995

Signed-off-by: Andrew Lytvynov <awly@tailscale.com>
This commit is contained in:
Andrew Lytvynov 2023-08-22 14:35:30 -06:00 committed by GitHub
parent 4b13e6e087
commit 7364c6beec
No known key found for this signature in database
GPG Key ID: 4AEE18F83AFDEB23
5 changed files with 758 additions and 0 deletions

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// Copyright (c) Tailscale Inc & AUTHORS
// SPDX-License-Identifier: BSD-3-Clause
// Package distsign implements signature and validation of arbitrary
// distributable files.
//
// There are 3 parties in this exchange:
// - builder, which creates files, signs them with signing keys and publishes
// to server
// - server, which distributes public signing keys, files and signatures
// - client, which downloads files and signatures from server, and validates
// the signatures
//
// There are 2 types of keys:
// - signing keys, that sign individual distributable files on the builder
// - root keys, that sign signing keys and are kept offline
//
// root keys -(sign)-> signing keys -(sign)-> files
//
// All keys are asymmetric Ed25519 key pairs.
//
// The server serves static files under some known prefix. The kinds of files are:
// - distsign.pub - bundle of PEM-encoded public signing keys
// - distsign.pub.sig - signature of distsign.pub using one of the root keys
// - $file - any distributable file
// - $file.sig - signature of $file using any of the signing keys
//
// The root public keys are baked into the client software at compile time.
// These keys are long-lived and prove the validity of current signing keys
// from distsign.pub. To rotate root keys, a new client release must be
// published, they are not rotated dynamically. There are multiple root keys in
// different locations specifically to allow this rotation without using the
// discarded root key for any new signatures.
//
// The signing public keys are fetched by the client dynamically before every
// download and can be rotated more readily, assuming that most deployed
// clients trust the root keys used to issue fresh signing keys.
package distsign
import (
"crypto"
"crypto/ed25519"
"crypto/rand"
"encoding/binary"
"encoding/pem"
"errors"
"fmt"
"hash"
"io"
"net/http"
"net/url"
"os"
"github.com/hdevalence/ed25519consensus"
"golang.org/x/crypto/blake2s"
)
const (
pemTypePrivate = "PRIVATE KEY"
pemTypePublic = "PUBLIC KEY"
downloadSizeLimit = 1 << 29 // 512MB
signingKeysSizeLimit = 1 << 20 // 1MB
signatureSizeLimit = ed25519.SignatureSize
)
// GenerateKey generates a new key pair and encodes it as PEM.
func GenerateKey() (priv, pub []byte, err error) {
pub, priv, err = ed25519.GenerateKey(rand.Reader)
if err != nil {
return nil, nil, err
}
return pem.EncodeToMemory(&pem.Block{
Type: pemTypePrivate,
Bytes: []byte(priv),
}), pem.EncodeToMemory(&pem.Block{
Type: pemTypePublic,
Bytes: []byte(pub),
}), nil
}
// RootKey is a root key Signer used to sign signing keys.
type RootKey Signer
// SignSigningKeys signs the bundle of public signing keys. The bundle must be
// a sequence of PEM blocks joined with newlines.
func (s *RootKey) SignSigningKeys(pubBundle []byte) ([]byte, error) {
return s.Sign(nil, pubBundle, crypto.Hash(0))
}
// SigningKey is a signing key Signer used to sign packages.
type SigningKey Signer
// SignPackageHash signs the hash and the length of a package. Use PackageHash
// to compute the inputs.
func (s SigningKey) SignPackageHash(hash []byte, len int64) ([]byte, error) {
if len <= 0 {
return nil, fmt.Errorf("package length must be positive, got %d", len)
}
msg := binary.LittleEndian.AppendUint64(hash, uint64(len))
return s.Sign(nil, msg, crypto.Hash(0))
}
// PackageHash is a hash.Hash that counts the number of bytes written. Use it
// to get the hash and length inputs to SigningKey.SignPackageHash.
type PackageHash struct {
hash.Hash
len int64
}
// NewPackageHash returns an initialized PackageHash using BLAKE2s.
func NewPackageHash() *PackageHash {
h, err := blake2s.New256(nil)
if err != nil {
// Should never happen with a nil key passed to blake2s.
panic(err)
}
return &PackageHash{Hash: h}
}
func (ph *PackageHash) Write(b []byte) (int, error) {
ph.len += int64(len(b))
return ph.Hash.Write(b)
}
// Reset the PackageHash to its initial state.
func (ph *PackageHash) Reset() {
ph.len = 0
ph.Hash.Reset()
}
// Len returns the total number of bytes written.
func (ph *PackageHash) Len() int64 { return ph.len }
// Signer is crypto.Signer using a single key (root or signing).
type Signer struct {
crypto.Signer
}
// NewSigner parses the PEM-encoded private key stored in the file named
// privKeyPath and creates a Signer for it. The key is expected to be in the
// same format as returned by GenerateKey.
func NewSigner(privKeyPath string) (Signer, error) {
raw, err := os.ReadFile(privKeyPath)
if err != nil {
return Signer{}, err
}
k, err := parsePrivateKey(raw)
if err != nil {
return Signer{}, fmt.Errorf("failed to parse %q: %w", privKeyPath, err)
}
return Signer{Signer: k}, nil
}
// Client downloads and validates files from a distribution server.
type Client struct {
roots []ed25519.PublicKey
pkgsAddr *url.URL
}
// NewClient returns a new client for distribution server located at pkgsAddr,
// and uses embedded root keys from the roots/ subdirectory of this package.
func NewClient(pkgsAddr string) (*Client, error) {
u, err := url.Parse(pkgsAddr)
if err != nil {
return nil, fmt.Errorf("invalid pkgsAddr %q: %w", pkgsAddr, err)
}
return &Client{roots: roots(), pkgsAddr: u}, nil
}
func (c *Client) url(path string) string {
return c.pkgsAddr.JoinPath(path).String()
}
// Download fetches a file at path srcPath from pkgsAddr passed in NewClient.
// The file is downloaded to dstPath and its signature is validated using the
// embedded root keys. Download returns an error if anything goes wrong with
// the actual file download or with signature validation.
func (c *Client) Download(srcPath, dstPath string) error {
// Always fetch a fresh signing key.
sigPub, err := c.signingKeys()
if err != nil {
return err
}
srcURL := c.url(srcPath)
sigURL := srcURL + ".sig"
dstPathUnverified := dstPath + ".unverified"
hash, len, err := download(srcURL, dstPathUnverified, downloadSizeLimit)
if err != nil {
return err
}
sig, err := fetch(sigURL, signatureSizeLimit)
if err != nil {
// Best-effort clean up of downloaded package.
os.Remove(dstPathUnverified)
return err
}
msg := binary.LittleEndian.AppendUint64(hash, uint64(len))
if !verifyAny(sigPub, msg, sig) {
// Best-effort clean up of downloaded package.
os.Remove(dstPathUnverified)
return fmt.Errorf("signature %q for key %q does not validate with the current release signing key; either you are under attack, or attempting to download an old version of Tailscale which was signed with an older signing key", sigURL, srcURL)
}
if err := os.Rename(dstPathUnverified, dstPath); err != nil {
return fmt.Errorf("failed to move %q to %q after signature validation", dstPathUnverified, dstPath)
}
return nil
}
// signingKeys fetches current signing keys from the server and validates them
// against the roots. Should be called before validation of any downloaded file
// to get the fresh keys.
func (c *Client) signingKeys() ([]ed25519.PublicKey, error) {
keyURL := c.url("distsign.pub")
sigURL := keyURL + ".sig"
raw, err := fetch(keyURL, signingKeysSizeLimit)
if err != nil {
return nil, err
}
sig, err := fetch(sigURL, signatureSizeLimit)
if err != nil {
return nil, err
}
if !verifyAny(c.roots, raw, sig) {
return nil, fmt.Errorf("signature %q for key %q does not validate with any known root key; either you are under attack, or running a very old version of Tailscale with outdated root keys", sigURL, keyURL)
}
// Parse the bundle of public signing keys.
var keys []ed25519.PublicKey
for len(raw) > 0 {
pub, rest, err := parsePublicKey(raw)
if err != nil {
return nil, err
}
keys = append(keys, pub)
raw = rest
}
if len(keys) == 0 {
return nil, fmt.Errorf("no signing keys found at %q", keyURL)
}
return keys, nil
}
// fetch reads the response body from url into memory, up to limit bytes.
func fetch(url string, limit int64) ([]byte, error) {
resp, err := http.Get(url)
if err != nil {
return nil, err
}
defer resp.Body.Close()
return io.ReadAll(io.LimitReader(resp.Body, limit))
}
// download writes the response body of url into a local file at dst, up to
// limit bytes. On success, the returned value is a BLAKE2s hash of the file.
func download(url, dst string, limit int64) ([]byte, int64, error) {
resp, err := http.Get(url)
if err != nil {
return nil, 0, err
}
defer resp.Body.Close()
h := NewPackageHash()
r := io.TeeReader(io.LimitReader(resp.Body, limit), h)
f, err := os.Create(dst)
if err != nil {
return nil, 0, err
}
defer f.Close()
if _, err := io.Copy(f, r); err != nil {
return nil, 0, err
}
if err := f.Close(); err != nil {
return nil, 0, err
}
return h.Sum(nil), h.Len(), nil
}
func parsePrivateKey(data []byte) (ed25519.PrivateKey, error) {
b, rest := pem.Decode(data)
if b == nil {
return nil, errors.New("failed to decode PEM data")
}
if len(rest) > 0 {
return nil, errors.New("trailing PEM data")
}
if b.Type != pemTypePrivate {
return nil, fmt.Errorf("PEM type is %q, want %q", b.Type, pemTypePrivate)
}
if len(b.Bytes) != ed25519.PrivateKeySize {
return nil, errors.New("private key has incorrect length for an Ed25519 private key")
}
return ed25519.PrivateKey(b.Bytes), nil
}
func parseSinglePublicKey(data []byte) (ed25519.PublicKey, error) {
pub, rest, err := parsePublicKey(data)
if err != nil {
return nil, err
}
if len(rest) > 0 {
return nil, errors.New("trailing PEM data")
}
return pub, err
}
func parsePublicKey(data []byte) (pub ed25519.PublicKey, rest []byte, retErr error) {
b, rest := pem.Decode(data)
if b == nil {
return nil, nil, errors.New("failed to decode PEM data")
}
if b.Type != pemTypePublic {
return nil, nil, fmt.Errorf("PEM type is %q, want %q", b.Type, pemTypePublic)
}
if len(b.Bytes) != ed25519.PublicKeySize {
return nil, nil, errors.New("public key has incorrect length for an Ed25519 public key")
}
return ed25519.PublicKey(b.Bytes), rest, nil
}
// verifyAny verifies whether sig is valid for msg using any of the keys.
// verifyAny will panic of any of the keys have the wrong size for Ed25519.
func verifyAny(keys []ed25519.PublicKey, msg, sig []byte) bool {
for _, k := range keys {
if ed25519consensus.Verify(k, msg, sig) {
return true
}
}
return false
}

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// Copyright (c) Tailscale Inc & AUTHORS
// SPDX-License-Identifier: BSD-3-Clause
package distsign
import (
"bytes"
"crypto/ed25519"
"net/http"
"net/http/httptest"
"net/url"
"os"
"path/filepath"
"strings"
"testing"
"golang.org/x/crypto/blake2s"
)
func TestDownload(t *testing.T) {
srv := newTestServer(t)
c := srv.client(t)
tests := []struct {
desc string
before func(*testing.T)
src string
want []byte
wantErr bool
}{
{
desc: "missing file",
before: func(*testing.T) {},
src: "hello",
wantErr: true,
},
{
desc: "success",
before: func(*testing.T) {
srv.addSigned("hello", []byte("world"))
},
src: "hello",
want: []byte("world"),
},
{
desc: "no signature",
before: func(*testing.T) {
srv.add("hello", []byte("world"))
},
src: "hello",
wantErr: true,
},
{
desc: "bad signature",
before: func(*testing.T) {
srv.add("hello", []byte("world"))
srv.add("hello.sig", []byte("potato"))
},
src: "hello",
wantErr: true,
},
{
desc: "signed with untrusted key",
before: func(t *testing.T) {
srv.add("hello", []byte("world"))
srv.add("hello.sig", newSigningKeyPair(t).sign([]byte("world")))
},
src: "hello",
wantErr: true,
},
{
desc: "signed with root key",
before: func(t *testing.T) {
srv.add("hello", []byte("world"))
srv.add("hello.sig", srv.roots[0].sign([]byte("world")))
},
src: "hello",
wantErr: true,
},
{
desc: "bad signing key signature",
before: func(t *testing.T) {
srv.add("distsign.pub.sig", []byte("potato"))
srv.addSigned("hello", []byte("world"))
},
src: "hello",
wantErr: true,
},
}
for _, tt := range tests {
t.Run(tt.desc, func(t *testing.T) {
srv.reset()
tt.before(t)
dst := filepath.Join(t.TempDir(), tt.src)
t.Cleanup(func() {
os.Remove(dst)
})
err := c.Download(tt.src, dst)
if err != nil {
if tt.wantErr {
return
}
t.Fatalf("unexpected error from Download(%q): %v", tt.src, err)
}
if tt.wantErr {
t.Fatalf("Download(%q) succeeded, expected an error", tt.src)
}
got, err := os.ReadFile(dst)
if err != nil {
t.Fatal(err)
}
if !bytes.Equal(tt.want, got) {
t.Errorf("Download(%q): got %q, want %q", tt.src, got, tt.want)
}
})
}
}
func TestRotateRoot(t *testing.T) {
srv := newTestServer(t)
c1 := srv.client(t)
srv.addSigned("hello", []byte("world"))
if err := c1.Download("hello", filepath.Join(t.TempDir(), "hello")); err != nil {
t.Fatalf("Download failed on a fresh server: %v", err)
}
// Remove first root and replace it with a new key.
srv.roots = append(srv.roots[1:], newRootKeyPair(t))
// Old client can still download files because it still trusts the old
// root key.
if err := c1.Download("hello", filepath.Join(t.TempDir(), "hello")); err != nil {
t.Fatalf("Download failed after root rotation on old client: %v", err)
}
// New client should fail download because current signing key is signed by
// the revoked root that new client doesn't trust.
c2 := srv.client(t)
if err := c2.Download("hello", filepath.Join(t.TempDir(), "hello")); err == nil {
t.Fatalf("Download succeeded on new client, but signing key is signed with revoked root key")
}
// Re-sign signing key with another valid root that client still trusts.
srv.resignSigningKeys()
// Both old and new clients should now be able to download.
//
// Note: we don't need to re-sign the "hello" file because signing key
// didn't change (only signing key's signature).
if err := c1.Download("hello", filepath.Join(t.TempDir(), "hello")); err != nil {
t.Fatalf("Download failed after root rotation on old client with re-signed signing key: %v", err)
}
if err := c2.Download("hello", filepath.Join(t.TempDir(), "hello")); err != nil {
t.Fatalf("Download failed after root rotation on new client with re-signed signing key: %v", err)
}
}
func TestRotateSigning(t *testing.T) {
srv := newTestServer(t)
c := srv.client(t)
srv.addSigned("hello", []byte("world"))
if err := c.Download("hello", filepath.Join(t.TempDir(), "hello")); err != nil {
t.Fatalf("Download failed on a fresh server: %v", err)
}
// Replace signing key but don't publish it yet.
srv.sign = append(srv.sign, newSigningKeyPair(t))
if err := c.Download("hello", filepath.Join(t.TempDir(), "hello")); err != nil {
t.Fatalf("Download failed after new signing key added but before publishing it: %v", err)
}
// Publish new signing key bundle with both keys.
srv.resignSigningKeys()
if err := c.Download("hello", filepath.Join(t.TempDir(), "hello")); err != nil {
t.Fatalf("Download failed after new signing key was published: %v", err)
}
// Re-sign the "hello" file with new signing key.
srv.add("hello.sig", srv.sign[1].sign([]byte("world")))
if err := c.Download("hello", filepath.Join(t.TempDir(), "hello")); err != nil {
t.Fatalf("Download failed after re-signing with new signing key: %v", err)
}
// Drop the old signing key.
srv.sign = srv.sign[1:]
srv.resignSigningKeys()
if err := c.Download("hello", filepath.Join(t.TempDir(), "hello")); err != nil {
t.Fatalf("Download failed after removing old signing key: %v", err)
}
// Add another key and re-sign the file with it *before* publishing.
srv.sign = append(srv.sign, newSigningKeyPair(t))
srv.add("hello.sig", srv.sign[1].sign([]byte("world")))
if err := c.Download("hello", filepath.Join(t.TempDir(), "hello")); err == nil {
t.Fatalf("Download succeeded when signed with a not-yet-published signing key")
}
// Fix this by publishing the new key.
srv.resignSigningKeys()
if err := c.Download("hello", filepath.Join(t.TempDir(), "hello")); err != nil {
t.Fatalf("Download failed after publishing new signing key: %v", err)
}
}
type testServer struct {
roots []rootKeyPair
sign []signingKeyPair
files map[string][]byte
srv *httptest.Server
}
func newTestServer(t *testing.T) *testServer {
var roots []rootKeyPair
for i := 0; i < 3; i++ {
roots = append(roots, newRootKeyPair(t))
}
ts := &testServer{
roots: roots,
sign: []signingKeyPair{newSigningKeyPair(t)},
}
ts.reset()
ts.srv = httptest.NewServer(ts)
t.Cleanup(ts.srv.Close)
return ts
}
func (s *testServer) client(t *testing.T) *Client {
roots := make([]ed25519.PublicKey, 0, len(s.roots))
for _, r := range s.roots {
pub, err := parseSinglePublicKey(r.pubRaw)
if err != nil {
t.Fatalf("parsePublicKey: %v", err)
}
roots = append(roots, pub)
}
u, err := url.Parse(s.srv.URL)
if err != nil {
t.Fatal(err)
}
return &Client{
roots: roots,
pkgsAddr: u,
}
}
func (s *testServer) ServeHTTP(w http.ResponseWriter, r *http.Request) {
path := strings.TrimPrefix(r.URL.Path, "/")
data, ok := s.files[path]
if !ok {
http.NotFound(w, r)
return
}
w.Write(data)
}
func (s *testServer) addSigned(name string, data []byte) {
s.files[name] = data
s.files[name+".sig"] = s.sign[0].sign(data)
}
func (s *testServer) add(name string, data []byte) {
s.files[name] = data
}
func (s *testServer) reset() {
s.files = make(map[string][]byte)
s.resignSigningKeys()
}
func (s *testServer) resignSigningKeys() {
var pubs [][]byte
for _, k := range s.sign {
pubs = append(pubs, k.pubRaw)
}
bundle := bytes.Join(pubs, []byte("\n"))
sig := s.roots[0].sign(bundle)
s.files["distsign.pub"] = bundle
s.files["distsign.pub.sig"] = sig
}
type rootKeyPair struct {
*RootKey
keyPair
}
func newRootKeyPair(t *testing.T) rootKeyPair {
kp := newKeyPair(t)
priv, err := parsePrivateKey(kp.privRaw)
if err != nil {
t.Fatalf("parsePrivateKey: %v", err)
}
return rootKeyPair{
RootKey: &RootKey{Signer: priv},
keyPair: kp,
}
}
func (s rootKeyPair) sign(bundle []byte) []byte {
sig, err := s.SignSigningKeys(bundle)
if err != nil {
panic(err)
}
return sig
}
type signingKeyPair struct {
*SigningKey
keyPair
}
func newSigningKeyPair(t *testing.T) signingKeyPair {
kp := newKeyPair(t)
priv, err := parsePrivateKey(kp.privRaw)
if err != nil {
t.Fatalf("parsePrivateKey: %v", err)
}
return signingKeyPair{
SigningKey: &SigningKey{Signer: priv},
keyPair: kp,
}
}
func (s signingKeyPair) sign(blob []byte) []byte {
hash := blake2s.Sum256(blob)
sig, err := s.SignPackageHash(hash[:], int64(len(blob)))
if err != nil {
panic(err)
}
return sig
}
type keyPair struct {
privRaw []byte
pubRaw []byte
}
func newKeyPair(t *testing.T) keyPair {
privRaw, pubRaw, err := GenerateKey()
if err != nil {
t.Fatalf("GenerateKey: %v", err)
}
return keyPair{
privRaw: privRaw,
pubRaw: pubRaw,
}
}

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// Copyright (c) Tailscale Inc & AUTHORS
// SPDX-License-Identifier: BSD-3-Clause
package distsign
import (
"crypto/ed25519"
"embed"
"errors"
"fmt"
"path"
"path/filepath"
"sync"
)
//go:embed roots
var rootsFS embed.FS
var roots = sync.OnceValue(func() []ed25519.PublicKey {
roots, err := parseRoots()
if err != nil {
panic(err)
}
return roots
})
func parseRoots() ([]ed25519.PublicKey, error) {
files, err := rootsFS.ReadDir("roots")
if err != nil {
return nil, err
}
var keys []ed25519.PublicKey
for _, f := range files {
if !f.Type().IsRegular() {
continue
}
if filepath.Ext(f.Name()) != ".pub" {
continue
}
raw, err := rootsFS.ReadFile(path.Join("roots", f.Name()))
if err != nil {
return nil, err
}
key, err := parseSinglePublicKey(raw)
if err != nil {
return nil, fmt.Errorf("parsing root key %q: %w", f.Name(), err)
}
keys = append(keys, key)
}
if len(keys) == 0 {
return nil, errors.New("no embedded root keys, please check clientupdate/distsign/roots/")
}
return keys, nil
}

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-----BEGIN PUBLIC KEY-----
JNBgo4EFQ+DpRcESM2xU19xQWGffvLcmxtBMT4I+Qo0=
-----END PUBLIC KEY-----

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// Copyright (c) Tailscale Inc & AUTHORS
// SPDX-License-Identifier: BSD-3-Clause
package distsign
import "testing"
func TestParseRoots(t *testing.T) {
roots, err := parseRoots()
if err != nil {
t.Fatal(err)
}
if len(roots) == 0 {
t.Error("parseRoots returned no root keys")
}
}