Add STARTTLS and SSL test cases for SMTP client

Extended test cases to include scenarios for STARTTLS and SSL connections. This includes handling TLS configurations, testing certificate handling, and tests for various authentication methods under TLS.

client_test.go

@@ -34,7 +34,7 @@ const (
 	// TestServerAddr is the address the simple SMTP test server listens on
 	TestServerAddr = "127.0.0.1"
 	// TestServerPortBase is the base port for the simple SMTP test server
-	TestServerPortBase = 2025
+	TestServerPortBase = 12025
 	// TestPasswordValid is the password that the test server accepts as valid for SMTP auth
 	TestPasswordValid = "V3ryS3cr3t+"
 	// TestUserValid is the username that the test server accepts as valid for SMTP auth
@@ -44,6 +44,44 @@ const (
 // PortAdder is an atomic counter used to increment port numbers for the test SMTP server instances.
 var PortAdder atomic.Int32
 
+// localhostCert is a PEM-encoded TLS cert generated from src/crypto/tls:
+//
+//	go run generate_cert.go --rsa-bits 1024 --host 127.0.0.1,::1,example.com \
+//		--ca --start-date "Jan 1 00:00:00 1970" --duration=1000000h
+var localhostCert = []byte(`
+-----BEGIN CERTIFICATE-----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+-----END CERTIFICATE-----`)
+
+// localhostKey is the private key for localhostCert.
+var localhostKey = []byte(testingKey(`
+-----BEGIN RSA TESTING KEY-----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+-----END RSA TESTING KEY-----`))
+
 // logLine represents a log entry with time, level, message, and direction details.
 type logLine struct {
 	Time      time.Time `json:"time"`
@@ -1668,7 +1706,7 @@ func TestClient_DialWithContext(t *testing.T) {
 		ctxDial, cancelDial := context.WithTimeout(ctx, time.Millisecond*500)
 		t.Cleanup(cancelDial)
 
-		client, err := NewClient(DefaultHost, WithPort(serverPort), WithTLSPolicy(NoTLS), WithDebugLog())
+		client, err := NewClient(DefaultHost, WithPort(serverPort), WithTLSPolicy(NoTLS))
 		if err != nil {
 			t.Fatalf("failed to create new client: %s", err)
 		}
@@ -1744,13 +1782,13 @@ func TestClient_DialWithContext(t *testing.T) {
 		}
 	})
 	t.Run("connect should fail on HELO", func(t *testing.T) {
-		ctx, cancel := context.WithCancel(context.Background())
+		ctxFail, cancelFail := context.WithCancel(context.Background())
-		defer cancel()
+		defer cancelFail()
 		PortAdder.Add(1)
 		failServerPort := int(TestServerPortBase + PortAdder.Load())
 		failFeatureSet := "250-AUTH PLAIN\r\n250-8BITMIME\r\n250-DSN\r\n250 SMTPUTF8"
 		go func() {
-			if err := simpleSMTPServer(ctx, &serverProps{
+			if err := simpleSMTPServer(ctxFail, &serverProps{
 				FailOnHelo: true,
 				FeatureSet: failFeatureSet,
 				ListenPort: failServerPort,
@@ -1778,7 +1816,113 @@ func TestClient_DialWithContext(t *testing.T) {
 			t.Errorf("client has no connection")
 		}
 	})
-	// TODO: Implement tests for TLS/SSL and custom DialCtxFunc
+	t.Run("connect with failing auth", func(t *testing.T) {
+		ctxDial, cancelDial := context.WithTimeout(ctx, time.Millisecond*500)
+		t.Cleanup(cancelDial)
+
+		client, err := NewClient(DefaultHost, WithPort(serverPort), WithTLSPolicy(NoTLS),
+			WithSMTPAuth(SMTPAuthPlain), WithUsername("invalid"), WithPassword("invalid"))
+		if err != nil {
+			t.Fatalf("failed to create new client: %s", err)
+		}
+		if err = client.DialWithContext(ctxDial); err == nil {
+			t.Fatalf("connection was supposed to fail, but didn't")
+		}
+	})
+	t.Run("connect with STARTTLS", func(t *testing.T) {
+		ctxTLS, cancelTLS := context.WithCancel(context.Background())
+		defer cancelTLS()
+		PortAdder.Add(1)
+		tlsServerPort := int(TestServerPortBase + PortAdder.Load())
+		tlsFeatureSet := "250-AUTH PLAIN\r\n250-8BITMIME\r\n250-DSN\r\n250-STARTTLS\r\n250 SMTPUTF8"
+		go func() {
+			if err := simpleSMTPServer(ctxTLS, &serverProps{
+				FeatureSet: tlsFeatureSet,
+				ListenPort: tlsServerPort,
+			}); err != nil {
+				t.Errorf("failed to start test server: %s", err)
+				return
+			}
+		}()
+		time.Sleep(time.Millisecond * 300)
+		ctxDial, cancelDial := context.WithTimeout(ctx, time.Millisecond*500)
+		t.Cleanup(cancelDial)
+
+		tlsConfig := &tls.Config{InsecureSkipVerify: true}
+		client, err := NewClient(DefaultHost, WithPort(tlsServerPort), WithTLSPolicy(TLSMandatory),
+			WithTLSConfig(tlsConfig), WithSMTPAuth(SMTPAuthPlain), WithUsername(TestUserValid),
+			WithPassword(TestPasswordValid))
+		if err != nil {
+			t.Fatalf("failed to create new client: %s", err)
+		}
+		if err = client.DialWithContext(ctxDial); err != nil {
+			t.Fatalf("failed to connect to the test server: %s", err)
+		}
+	})
+	t.Run("want STARTTLS, but server does not support it", func(t *testing.T) {
+		ctxTLS, cancelTLS := context.WithCancel(context.Background())
+		defer cancelTLS()
+		PortAdder.Add(1)
+		tlsServerPort := int(TestServerPortBase + PortAdder.Load())
+		tlsFeatureSet := "250-AUTH PLAIN\r\n250-8BITMIME\r\n250-DSN\r\n250 SMTPUTF8"
+		go func() {
+			if err := simpleSMTPServer(ctxTLS, &serverProps{
+				FeatureSet: tlsFeatureSet,
+				ListenPort: tlsServerPort,
+			}); err != nil {
+				t.Errorf("failed to start test server: %s", err)
+				return
+			}
+		}()
+		time.Sleep(time.Millisecond * 300)
+		ctxDial, cancelDial := context.WithTimeout(ctx, time.Millisecond*500)
+		t.Cleanup(cancelDial)
+
+		tlsConfig := &tls.Config{InsecureSkipVerify: true}
+		client, err := NewClient(DefaultHost, WithPort(tlsServerPort), WithTLSPolicy(TLSMandatory),
+			WithTLSConfig(tlsConfig), WithSMTPAuth(SMTPAuthPlain), WithUsername(TestUserValid),
+			WithPassword(TestPasswordValid))
+		if err != nil {
+			t.Fatalf("failed to create new client: %s", err)
+		}
+		if err = client.DialWithContext(ctxDial); err == nil {
+			t.Fatalf("connection was supposed to fail, but didn't")
+		}
+	})
+	t.Run("connect with SSL", func(t *testing.T) {
+		ctxSSL, cancelSSL := context.WithCancel(context.Background())
+		defer cancelSSL()
+		PortAdder.Add(1)
+		sslServerPort := int(TestServerPortBase + PortAdder.Load())
+		sslFeatureSet := "250-AUTH PLAIN\r\n250-8BITMIME\r\n250-DSN\r\n250 SMTPUTF8"
+		go func() {
+			if err := simpleSMTPServer(ctxSSL, &serverProps{
+				SSLListener: true,
+				FeatureSet:  sslFeatureSet,
+				ListenPort:  sslServerPort,
+			}); err != nil {
+				t.Errorf("failed to start test server: %s", err)
+				return
+			}
+		}()
+		time.Sleep(time.Millisecond * 300)
+		ctxDial, cancelDial := context.WithTimeout(ctx, time.Millisecond*500)
+		t.Cleanup(cancelDial)
+
+		tlsConfig := &tls.Config{InsecureSkipVerify: true}
+		client, err := NewClient(DefaultHost, WithPort(sslServerPort), WithSSL(),
+			WithTLSConfig(tlsConfig), WithSMTPAuth(SMTPAuthPlain), WithUsername(TestUserValid),
+			WithPassword(TestPasswordValid))
+		if err != nil {
+			t.Fatalf("failed to create new client: %s", err)
+		}
+		if err = client.DialWithContext(ctxDial); err != nil {
+			t.Fatalf("failed to connect to the test server: %s", err)
+		}
+		if err := client.Close(); err != nil {
+			t.Fatalf("failed to close client: %s", err)
+		}
+	})
 }
 
 /*
@@ -3641,12 +3785,19 @@ func parseJSONLog(t *testing.T, buf *bytes.Buffer) logData {
 	return logdata
 }
 
+// testingKey replaces the substring "TESTING KEY" with "PRIVATE KEY" in the given string s.
+func testingKey(s string) string { return strings.ReplaceAll(s, "TESTING KEY", "PRIVATE KEY") }
+
+// serverProps represents the configuration properties for the SMTP server.
 type serverProps struct {
 	FailOnHelo     bool
 	FailOnQuit     bool
 	FailOnReset    bool
+	FailOnSTARTTLS bool
 	FeatureSet     string
 	ListenPort     int
+	SSLListener    bool
+	IsTLS          bool
 }
 
 // simpleSMTPServer starts a simple TCP server that resonds to SMTP commands.
@@ -3656,9 +3807,23 @@ func simpleSMTPServer(ctx context.Context, props *serverProps) error {
 	if props == nil {
 		return fmt.Errorf("no server properties provided")
 	}
-	listener, err := net.Listen(TestServerProto, fmt.Sprintf("%s:%d", TestServerAddr, props.ListenPort))
+
+	var listener net.Listener
+	var err error
+	if props.SSLListener {
+		keypair, err := tls.X509KeyPair(localhostCert, localhostKey)
 		if err != nil {
-		return fmt.Errorf("unable to listen on %s://%s: %w", TestServerProto, TestServerAddr, err)
+			return fmt.Errorf("failed to read TLS keypair: %s", err)
+		}
+		tlsConfig := &tls.Config{Certificates: []tls.Certificate{keypair}}
+		listener, err = tls.Listen(TestServerProto, fmt.Sprintf("%s:%d", TestServerAddr, props.ListenPort),
+			tlsConfig)
+	} else {
+		listener, err = net.Listen(TestServerProto, fmt.Sprintf("%s:%d", TestServerAddr, props.ListenPort))
+	}
+	if err != nil {
+		return fmt.Errorf("unable to listen on %s://%s: %w (SSL: %t)", TestServerProto, TestServerAddr, err,
+			props.SSLListener)
 	}
 
 	defer func() {
@@ -3707,10 +3872,12 @@ func handleTestServerConnection(connection net.Conn, props *serverProps) {
 		_ = writeLine("250 2.0.0 OK")
 	}
 
+	if !props.IsTLS {
 		if err := writeLine("220 go-mail test server ready ESMTP"); err != nil {
 			fmt.Printf("unable to write to client: %s\n", err)
 			return
 		}
+	}
 
 	for {
 		data, err := reader.ReadString('\n')
@@ -3850,6 +4017,21 @@ func handleTestServerConnection(connection net.Conn, props *serverProps) {
 			}
 			_ = writeLine("221 2.0.0 Bye")
 			return
+		case strings.EqualFold(data, "starttls"):
+			if props.FailOnSTARTTLS {
+				_ = writeLine("500 5.1.2 Error: starttls failed")
+				break
+			}
+			keypair, err := tls.X509KeyPair(localhostCert, localhostKey)
+			if err != nil {
+				_ = writeLine("500 5.1.2 Error: starttls failed - " + err.Error())
+				break
+			}
+			_ = writeLine("220 Ready to start TLS")
+			tlsConfig := &tls.Config{Certificates: []tls.Certificate{keypair}}
+			connection = tls.Server(connection, tlsConfig)
+			props.IsTLS = true
+			handleTestServerConnection(connection, props)
 		default:
 			_ = writeLine("500 5.5.2 Error: bad syntax")
 		}