1 files changed, 56 insertions, 39 deletions

diff --git a/services/mailer/mailer.go b/services/mailer/mailer.go
index f4bc2ddc63..c86c54c748 100644
--- a/services/mailer/mailer.go
+++ b/services/mailer/mailer.go
@@ -147,65 +147,82 @@ type smtpSender struct{}
 func (s *smtpSender) Send(from string, to []string, msg io.WriterTo) error {
 	opts := setting.MailService
 
-	host, port, err := net.SplitHostPort(opts.Host)
-	if err != nil {
-		return err
+	var network string
+	var address string
+	if opts.Protocol == "smtp+unix" {
+		network = "unix"
+		address = opts.SMTPAddr
+	} else {
+		network = "tcp"
+		address = net.JoinHostPort(opts.SMTPAddr, opts.SMTPPort)
 	}
 
-	tlsconfig := &tls.Config{
-		InsecureSkipVerify: opts.SkipVerify,
-		ServerName:         host,
+	conn, err := net.Dial(network, address)
+	if err != nil {
+		return fmt.Errorf("failed to establish network connection to SMTP server: %v", err)
 	}
+	defer conn.Close()
 
-	if opts.UseCertificate {
-		cert, err := tls.LoadX509KeyPair(opts.CertFile, opts.KeyFile)
-		if err != nil {
-			return err
+	var tlsconfig *tls.Config
+	if opts.Protocol == "smtps" || opts.Protocol == "smtp+startls" {
+		tlsconfig = &tls.Config{
+			InsecureSkipVerify: opts.ForceTrustServerCert,
+			ServerName:         opts.SMTPAddr,
 		}
-		tlsconfig.Certificates = []tls.Certificate{cert}
-	}
 
-	conn, err := net.Dial("tcp", net.JoinHostPort(host, port))
-	if err != nil {
-		return err
+		if opts.UseClientCert {
+			cert, err := tls.LoadX509KeyPair(opts.ClientCertFile, opts.ClientKeyFile)
+			if err != nil {
+				return fmt.Errorf("could not load SMTP client certificate: %v", err)
+			}
+			tlsconfig.Certificates = []tls.Certificate{cert}
+		}
 	}
-	defer conn.Close()
 
-	isSecureConn := opts.IsTLSEnabled || (strings.HasSuffix(port, "465"))
-	// Start TLS directly if the port ends with 465 (SMTPS protocol)
-	if isSecureConn {
+	if opts.Protocol == "smtps" {
 		conn = tls.Client(conn, tlsconfig)
 	}
 
+	host := "localhost"
+	if opts.Protocol == "smtp+unix" {
+		host = opts.SMTPAddr
+	}
 	client, err := smtp.NewClient(conn, host)
 	if err != nil {
-		return fmt.Errorf("NewClient: %v", err)
+		return fmt.Errorf("could not initiate SMTP session: %v", err)
 	}
 
-	if !opts.DisableHelo {
+	if opts.EnableHelo {
 		hostname := opts.HeloHostname
 		if len(hostname) == 0 {
 			hostname, err = os.Hostname()
 			if err != nil {
-				return err
+				return fmt.Errorf("could not retrieve system hostname: %v", err)
 			}
 		}
 
 		if err = client.Hello(hostname); err != nil {
-			return fmt.Errorf("Hello: %v", err)
+			return fmt.Errorf("failed to issue HELO command: %v", err)
 		}
 	}
 
-	// If not using SMTPS, always use STARTTLS if available
-	hasStartTLS, _ := client.Extension("STARTTLS")
-	if !isSecureConn && hasStartTLS {
-		if err = client.StartTLS(tlsconfig); err != nil {
-			return fmt.Errorf("StartTLS: %v", err)
+	if opts.Protocol == "smtp+startls" {
+		hasStartTLS, _ := client.Extension("STARTTLS")
+		if hasStartTLS {
+			if err = client.StartTLS(tlsconfig); err != nil {
+				return fmt.Errorf("failed to start TLS connection: %v", err)
+			}
+		} else {
+			log.Warn("StartTLS requested, but SMTP server does not support it; falling back to regular SMTP")
 		}
 	}
 
 	canAuth, options := client.Extension("AUTH")
-	if canAuth && len(opts.User) > 0 {
+	if len(opts.User) > 0 {
+		if !canAuth {
+			return fmt.Errorf("SMTP server does not support AUTH, but credentials provided")
+		}
+
 		var auth smtp.Auth
 
 		if strings.Contains(options, "CRAM-MD5") {
@@ -219,34 +236,34 @@ func (s *smtpSender) Send(from string, to []string, msg io.WriterTo) error {
 
 		if auth != nil {
 			if err = client.Auth(auth); err != nil {
-				return fmt.Errorf("Auth: %v", err)
+				return fmt.Errorf("failed to authenticate SMTP: %v", err)
 			}
 		}
 	}
 
 	if opts.OverrideEnvelopeFrom {
 		if err = client.Mail(opts.EnvelopeFrom); err != nil {
-			return fmt.Errorf("Mail: %v", err)
+			return fmt.Errorf("failed to issue MAIL command: %v", err)
 		}
 	} else {
 		if err = client.Mail(from); err != nil {
-			return fmt.Errorf("Mail: %v", err)
+			return fmt.Errorf("failed to issue MAIL command: %v", err)
 		}
 	}
 
 	for _, rec := range to {
 		if err = client.Rcpt(rec); err != nil {
-			return fmt.Errorf("Rcpt: %v", err)
+			return fmt.Errorf("failed to issue RCPT command: %v", err)
 		}
 	}
 
 	w, err := client.Data()
 	if err != nil {
-		return fmt.Errorf("Data: %v", err)
+		return fmt.Errorf("failed to issue DATA command: %v", err)
 	} else if _, err = msg.WriteTo(w); err != nil {
-		return fmt.Errorf("WriteTo: %v", err)
+		return fmt.Errorf("SMTP write failed: %v", err)
 	} else if err = w.Close(); err != nil {
-		return fmt.Errorf("Close: %v", err)
+		return fmt.Errorf("SMTP close failed: %v", err)
 	}
 
 	return client.Quit()
@@ -338,13 +355,13 @@ func NewContext() {
 		return
 	}
 
-	switch setting.MailService.MailerType {
-	case "smtp":
-		Sender = &smtpSender{}
+	switch setting.MailService.Protocol {
 	case "sendmail":
 		Sender = &sendmailSender{}
 	case "dummy":
 		Sender = &dummySender{}
+	default:
+		Sender = &smtpSender{}
 	}
 
 	mailQueue = queue.CreateQueue("mail", func(data ...queue.Data) []queue.Data {