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75 changes: 70 additions & 5 deletions transport/tls/stream_dialer_test.go
Original file line number Diff line number Diff line change
Expand Up @@ -19,15 +19,16 @@ import (
"crypto/ecdsa"
"crypto/elliptic"
"crypto/rand"
stdTLS "crypto/tls"
"crypto/x509"
"crypto/x509/pkix"
"math/big"
"net"
"testing"
"time"

"golang.getoutline.org/sdk/transport"
"github.com/stretchr/testify/require"
"golang.getoutline.org/sdk/transport"
)

func TestDomain(t *testing.T) {
Expand All @@ -44,17 +45,53 @@ func TestDomain(t *testing.T) {
}

func TestUntrustedRoot(t *testing.T) {
sd, err := NewStreamDialer(&transport.TCPDialer{})
now := time.Now()
rootCA, rootKey := createRootCA(t)
leafCert, leafKey := createLeafCert(t,
[]string{"localhost"},
[]net.IP{net.ParseIP("127.0.0.1")},
rootCA, rootKey,
now.Add(-time.Hour), now.Add(time.Hour),
)

addr := serveTLSHandshakes(t, stdTLS.Certificate{
Certificate: [][]byte{leafCert.Raw},
PrivateKey: leafKey,
})
host, _, err := net.SplitHostPort(addr)
require.NoError(t, err)
_, err = sd.DialStream(context.Background(), "untrusted-root.badssl.com:443")

verifier := &StandardCertVerifier{CertificateName: host, Roots: x509.NewCertPool()}
sd, err := NewStreamDialer(&transport.TCPDialer{}, WithCertVerifier(verifier))
require.NoError(t, err)
_, err = sd.DialStream(context.Background(), addr)
var certErr x509.UnknownAuthorityError
require.ErrorAs(t, err, &certErr)
}

func TestExpired(t *testing.T) {
sd, err := NewStreamDialer(&transport.TCPDialer{})
now := time.Now()
rootCA, rootKey := createRootCA(t)
leafCert, leafKey := createLeafCert(t,
[]string{"localhost"},
[]net.IP{net.ParseIP("127.0.0.1")},
rootCA, rootKey,
now.Add(-2*time.Hour), now.Add(-time.Hour),
)
rootPool := x509.NewCertPool()
rootPool.AddCert(rootCA)

addr := serveTLSHandshakes(t, stdTLS.Certificate{
Certificate: [][]byte{leafCert.Raw},
PrivateKey: leafKey,
})
host, _, err := net.SplitHostPort(addr)
require.NoError(t, err)
_, err = sd.DialStream(context.Background(), "expired.badssl.com:443")

verifier := &StandardCertVerifier{CertificateName: host, Roots: rootPool}
sd, err := NewStreamDialer(&transport.TCPDialer{}, WithCertVerifier(verifier))
require.NoError(t, err)
_, err = sd.DialStream(context.Background(), addr)
var certErr x509.CertificateInvalidError
require.ErrorAs(t, err, &certErr)
require.Equal(t, x509.Expired, certErr.Reason)
Expand Down Expand Up @@ -171,6 +208,34 @@ type countedStreamConn struct {
counter *connCounterDialer
}

func serveTLSHandshakes(t *testing.T, cert stdTLS.Certificate) string {
t.Helper()

listener, err := stdTLS.Listen("tcp", "127.0.0.1:0", &stdTLS.Config{Certificates: []stdTLS.Certificate{cert}})
require.NoError(t, err)

done := make(chan struct{})
go func() {
defer close(done)
for {
conn, err := listener.Accept()
if err != nil {
return
}
go func(conn net.Conn) {
defer conn.Close()
_ = conn.(*stdTLS.Conn).Handshake()
}(conn)
}
}()

t.Cleanup(func() {
require.NoError(t, listener.Close())
<-done
})
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return listener.Addr().String()
}

func (d *connCounterDialer) DialStream(ctx context.Context, raddr string) (transport.StreamConn, error) {
conn, err := d.base.DialStream(ctx, raddr)
if conn != nil {
Expand Down
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