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feat: support multiple certificates in coder server and helm #4150

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Merged
merged 4 commits into from
Oct 4, 2022
Merged

feat: support multiple certificates in coder server and helm #4150

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cbfbc79
feat: support multiple certificates in coder server and helm
deansheather Sep 22, 2022
2d2df29
chore: multi-cert tests for coder server
deansheather Sep 29, 2022
da652ab
fixup! chore: multi-cert tests for coder server
deansheather Sep 29, 2022
d4f5448
fixup! chore: multi-cert tests for coder server
deansheather Oct 1, 2022
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91 changes: 55 additions & 36 deletions cli/server.go
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Original file line number Diff line number Diff line change
Expand Up @@ -5,7 +5,6 @@ import (
"crypto/tls"
"crypto/x509"
"database/sql"
"encoding/pem"
"errors"
"fmt"
"io"
Expand Down Expand Up @@ -104,11 +103,11 @@ func Server(newAPI func(context.Context, *coderd.Options) (*coderd.API, error))
tailscaleEnable bool
telemetryEnable bool
telemetryURL string
tlsCertFile string
tlsCertFiles []string
tlsClientCAFile string
tlsClientAuth string
tlsEnable bool
tlsKeyFile string
tlsKeyFiles []string
tlsMinVersion string
tunnel bool
traceEnable bool
Expand Down Expand Up @@ -210,7 +209,7 @@ func Server(newAPI func(context.Context, *coderd.Options) (*coderd.API, error))
defer listener.Close()

if tlsEnable {
listener, err = configureTLS(listener, tlsMinVersion, tlsClientAuth, tlsCertFile, tlsKeyFile, tlsClientCAFile)
listener, err = configureServerTLS(listener, tlsMinVersion, tlsClientAuth, tlsCertFiles, tlsKeyFiles, tlsClientCAFile)
if err != nil {
return xerrors.Errorf("configure tls: %w", err)
}
Expand Down Expand Up @@ -817,17 +816,17 @@ func Server(newAPI func(context.Context, *coderd.Options) (*coderd.API, error))
_ = root.Flags().MarkHidden("telemetry-url")
cliflag.BoolVarP(root.Flags(), &tlsEnable, "tls-enable", "", "CODER_TLS_ENABLE", false,
"Whether TLS will be enabled.")
cliflag.StringVarP(root.Flags(), &tlsCertFile, "tls-cert-file", "", "CODER_TLS_CERT_FILE", "",
"Path to the certificate for TLS. It requires a PEM-encoded file. "+
cliflag.StringArrayVarP(root.Flags(), &tlsCertFiles, "tls-cert-file", "", "CODER_TLS_CERT_FILE", []string{},
"Path to each certificate for TLS. It requires a PEM-encoded file. "+
"To configure the listener to use a CA certificate, concatenate the primary certificate "+
"and the CA certificate together. The primary certificate should appear first in the combined file.")
cliflag.StringVarP(root.Flags(), &tlsClientCAFile, "tls-client-ca-file", "", "CODER_TLS_CLIENT_CA_FILE", "",
"PEM-encoded Certificate Authority file used for checking the authenticity of client")
cliflag.StringVarP(root.Flags(), &tlsClientAuth, "tls-client-auth", "", "CODER_TLS_CLIENT_AUTH", "request",
`Policy the server will follow for TLS Client Authentication. `+
`Accepted values are "none", "request", "require-any", "verify-if-given", or "require-and-verify"`)
cliflag.StringVarP(root.Flags(), &tlsKeyFile, "tls-key-file", "", "CODER_TLS_KEY_FILE", "",
"Path to the private key for the certificate. It requires a PEM-encoded file")
cliflag.StringArrayVarP(root.Flags(), &tlsKeyFiles, "tls-key-file", "", "CODER_TLS_KEY_FILE", []string{},
"Paths to the private keys for each of the certificates. It requires a PEM-encoded file")
cliflag.StringVarP(root.Flags(), &tlsMinVersion, "tls-min-version", "", "CODER_TLS_MIN_VERSION", "tls12",
`Minimum supported version of TLS. Accepted values are "tls10", "tls11", "tls12" or "tls13"`)
cliflag.BoolVarP(root.Flags(), &tunnel, "tunnel", "", "CODER_TUNNEL", false,
Expand Down Expand Up @@ -1015,7 +1014,32 @@ func printLogo(cmd *cobra.Command, spooky bool) {
_, _ = fmt.Fprintf(cmd.OutOrStdout(), "%s - Remote development on your infrastucture\n", cliui.Styles.Bold.Render("Coder "+buildinfo.Version()))
}

func configureTLS(listener net.Listener, tlsMinVersion, tlsClientAuth, tlsCertFile, tlsKeyFile, tlsClientCAFile string) (net.Listener, error) {
func loadCertificates(tlsCertFiles, tlsKeyFiles []string) ([]tls.Certificate, error) {
if len(tlsCertFiles) != len(tlsKeyFiles) {
return nil, xerrors.New("--tls-cert-file and --tls-key-file must be used the same amount of times")
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Suggested change
return nil, xerrors.New("--tls-cert-file and --tls-key-file must be used the same amount of times")
return nil, xerrors.New("the number of --tls-cert-file and --tls-key-file must be the same")

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I personally think the old message is better, what do you think @kylecarbs

}
if len(tlsCertFiles) == 0 {
return nil, xerrors.New("--tls-cert-file is required when tls is enabled")
}
if len(tlsKeyFiles) == 0 {
return nil, xerrors.New("--tls-key-file is required when tls is enabled")
}

certs := make([]tls.Certificate, len(tlsCertFiles))
for i := range tlsCertFiles {
certFile, keyFile := tlsCertFiles[i], tlsKeyFiles[i]
cert, err := tls.LoadX509KeyPair(certFile, keyFile)
if err != nil {
return nil, xerrors.Errorf("load TLS key pair %d (%q, %q): %w", i, certFile, keyFile, err)
}

certs[i] = cert
}

return certs, nil
}

func configureServerTLS(listener net.Listener, tlsMinVersion, tlsClientAuth string, tlsCertFiles, tlsKeyFiles []string, tlsClientCAFile string) (net.Listener, error) {
tlsConfig := &tls.Config{
MinVersion: tls.VersionTLS12,
}
Expand Down Expand Up @@ -1047,36 +1071,31 @@ func configureTLS(listener net.Listener, tlsMinVersion, tlsClientAuth, tlsCertFi
return nil, xerrors.Errorf("unrecognized tls client auth: %q", tlsClientAuth)
}

if tlsCertFile == "" {
return nil, xerrors.New("tls-cert-file is required when tls is enabled")
}
if tlsKeyFile == "" {
return nil, xerrors.New("tls-key-file is required when tls is enabled")
}

certPEMBlock, err := os.ReadFile(tlsCertFile)
if err != nil {
return nil, xerrors.Errorf("read file %q: %w", tlsCertFile, err)
}
keyPEMBlock, err := os.ReadFile(tlsKeyFile)
certs, err := loadCertificates(tlsCertFiles, tlsKeyFiles)
if err != nil {
return nil, xerrors.Errorf("read file %q: %w", tlsKeyFile, err)
}
keyBlock, _ := pem.Decode(keyPEMBlock)
if keyBlock == nil {
return nil, xerrors.New("decoded pem is blank")
}
cert, err := tls.X509KeyPair(certPEMBlock, keyPEMBlock)
if err != nil {
return nil, xerrors.Errorf("create key pair: %w", err)
}
tlsConfig.GetCertificate = func(chi *tls.ClientHelloInfo) (*tls.Certificate, error) {
return &cert, nil
return nil, xerrors.Errorf("load certificates: %w", err)
}
tlsConfig.GetCertificate = func(hi *tls.ClientHelloInfo) (*tls.Certificate, error) {
// If there's only one certificate, return it.
if len(certs) == 1 {
return &certs[0], nil
}

// Expensively check which certificate matches the client hello.
for _, cert := range certs {
cert := cert
if err := hi.SupportsCertificate(&cert); err == nil {
return &cert, nil
}
}

certPool := x509.NewCertPool()
certPool.AppendCertsFromPEM(certPEMBlock)
tlsConfig.RootCAs = certPool
// Return the first certificate if we have one, or return nil so the
// server doesn't fail.
if len(certs) > 0 {
return &certs[0], nil
}
return nil, nil //nolint:nilnil
}

if tlsClientCAFile != "" {
caPool := x509.NewCertPool()
Expand Down
158 changes: 145 additions & 13 deletions cli/server_test.go
View file
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Original file line number Diff line number Diff line change
Expand Up @@ -21,6 +21,7 @@ import (
"runtime"
"strconv"
"strings"
"sync/atomic"
"testing"
"time"

Expand Down Expand Up @@ -240,20 +241,64 @@ func TestServer(t *testing.T) {
err := root.ExecuteContext(ctx)
require.Error(t, err)
})
t.Run("TLSNoCertFile", func(t *testing.T) {
t.Run("TLSInvalid", func(t *testing.T) {
t.Parallel()
ctx, cancelFunc := context.WithCancel(context.Background())
defer cancelFunc()

root, _ := clitest.New(t,
"server",
"--in-memory",
"--address", ":0",
"--tls-enable",
"--cache-dir", t.TempDir(),
)
err := root.ExecuteContext(ctx)
require.Error(t, err)
cert1Path, key1Path := generateTLSCertificate(t)
cert2Path, key2Path := generateTLSCertificate(t)

cases := []struct {
name string
args []string
errContains string
}{
{
name: "NoCertAndKey",
args: []string{"--tls-enable"},
errContains: "--tls-cert-file is required when tls is enabled",
},
{
name: "NoCert",
args: []string{"--tls-enable", "--tls-key-file", key1Path},
errContains: "--tls-cert-file and --tls-key-file must be used the same amount of times",
},
{
name: "NoKey",
args: []string{"--tls-enable", "--tls-cert-file", cert1Path},
errContains: "--tls-cert-file and --tls-key-file must be used the same amount of times",
},
{
name: "MismatchedCount",
args: []string{"--tls-enable", "--tls-cert-file", cert1Path, "--tls-key-file", key1Path, "--tls-cert-file", cert2Path},
errContains: "--tls-cert-file and --tls-key-file must be used the same amount of times",
},
{
name: "MismatchedCertAndKey",
args: []string{"--tls-enable", "--tls-cert-file", cert1Path, "--tls-key-file", key2Path},
errContains: "load TLS key pair",
},
}

for _, c := range cases {
c := c
t.Run(c.name, func(t *testing.T) {
t.Parallel()
ctx, cancelFunc := context.WithCancel(context.Background())
defer cancelFunc()

args := []string{
"server",
"--in-memory",
"--address", ":0",
"--cache-dir", t.TempDir(),
}
args = append(args, c.args...)
root, _ := clitest.New(t, args...)
err := root.ExecuteContext(ctx)
require.Error(t, err)
require.ErrorContains(t, err, c.errContains)
})
}
})
t.Run("TLSValid", func(t *testing.T) {
t.Parallel()
Expand Down Expand Up @@ -293,6 +338,86 @@ func TestServer(t *testing.T) {
cancelFunc()
require.NoError(t, <-errC)
})
t.Run("TLSValidMultiple", func(t *testing.T) {
t.Parallel()
ctx, cancelFunc := context.WithCancel(context.Background())
defer cancelFunc()

cert1Path, key1Path := generateTLSCertificate(t, "alpaca.com")
cert2Path, key2Path := generateTLSCertificate(t, "*.llama.com")
root, cfg := clitest.New(t,
"server",
"--in-memory",
"--address", ":0",
"--tls-enable",
"--tls-cert-file", cert1Path,
"--tls-key-file", key1Path,
"--tls-cert-file", cert2Path,
"--tls-key-file", key2Path,
"--cache-dir", t.TempDir(),
)
errC := make(chan error, 1)
go func() {
errC <- root.ExecuteContext(ctx)
}()
accessURL := waitAccessURL(t, cfg)
require.Equal(t, "https", accessURL.Scheme)
originalHost := accessURL.Host

var (
expectAddr string
dials int64
)
client := codersdk.New(accessURL)
client.HTTPClient = &http.Client{
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Could add the certs to the client. But not a big deal as you verify hostname later 🤷

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I'm going to leave this as-is because we will get better test failure messages if the server somehow returns an unexpected certificate

Transport: &http.Transport{
DialTLSContext: func(ctx context.Context, network, addr string) (net.Conn, error) {
atomic.AddInt64(&dials, 1)
assert.Equal(t, expectAddr, addr)

host, _, err := net.SplitHostPort(addr)
require.NoError(t, err)

// Always connect to the accessURL ip:port regardless of
// hostname.
conn, err := tls.Dial(network, originalHost, &tls.Config{
MinVersion: tls.VersionTLS12,
//nolint:gosec
InsecureSkipVerify: true,
ServerName: host,
})
if err != nil {
return nil, err
}

// We can't call conn.VerifyHostname because it requires
// that the certificates are valid, so we call
// VerifyHostname on the first certificate instead.
require.Len(t, conn.ConnectionState().PeerCertificates, 1)
err = conn.ConnectionState().PeerCertificates[0].VerifyHostname(host)
assert.NoError(t, err, "invalid cert common name")
return conn, nil
},
},
}

// Use the first certificate and hostname.
client.URL.Host = "alpaca.com:443"
expectAddr = "alpaca.com:443"
_, err := client.HasFirstUser(ctx)
require.NoError(t, err)
require.EqualValues(t, 1, atomic.LoadInt64(&dials))

// Use the second certificate (wildcard) and hostname.
client.URL.Host = "hi.llama.com:443"
expectAddr = "hi.llama.com:443"
_, err = client.HasFirstUser(ctx)
require.NoError(t, err)
require.EqualValues(t, 2, atomic.LoadInt64(&dials))

cancelFunc()
require.NoError(t, <-errC)
})
// This cannot be ran in parallel because it uses a signal.
//nolint:paralleltest
t.Run("Shutdown", func(t *testing.T) {
Expand Down Expand Up @@ -480,16 +605,22 @@ func TestServer(t *testing.T) {
})
}

func generateTLSCertificate(t testing.TB) (certPath, keyPath string) {
func generateTLSCertificate(t testing.TB, commonName ...string) (certPath, keyPath string) {
dir := t.TempDir()

commonNameStr := "localhost"
if len(commonName) > 0 {
commonNameStr = commonName[0]
}
privateKey, err := ecdsa.GenerateKey(elliptic.P256(), rand.Reader)
require.NoError(t, err)
template := x509.Certificate{
SerialNumber: big.NewInt(1),
Subject: pkix.Name{
Organization: []string{"Acme Co"},
CommonName: commonNameStr,
},
DNSNames: []string{commonNameStr},
NotBefore: time.Now(),
NotAfter: time.Now().Add(time.Hour * 24 * 180),

Expand All @@ -498,6 +629,7 @@ func generateTLSCertificate(t testing.TB) (certPath, keyPath string) {
BasicConstraintsValid: true,
IPAddresses: []net.IP{net.ParseIP("127.0.0.1")},
}

derBytes, err := x509.CreateCertificate(rand.Reader, &template, &template, &privateKey.PublicKey, privateKey)
require.NoError(t, err)
certFile, err := os.CreateTemp(dir, "")
Expand Down
8 changes: 8 additions & 0 deletions helm/templates/NOTES.txt
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Original file line number Diff line number Diff line change
@@ -0,0 +1,8 @@
{{- if .Values.coder.tls.secretName }}

WARN: coder.tls.secretName is deprecated and will be removed in a future
release. Please use coder.tls.secretNames instead.
{{- end }}

Enjoy Coder! Please create an issue at https://github.com/coder/coder if you run
into any problems! :)
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