Merge pull request #386 from wneessen/bug/385_concurrency-issue-in-dialandsendwithcontext

Fix concurrency issue in DialAndSendWithContext

client.go

@@ -142,9 +142,6 @@ type (
 		// host is the hostname of the SMTP server we are connecting to.
 		host string
 
-		// isEncrypted indicates wether the Client connection is encrypted or not.
-		isEncrypted bool
-
 		// logAuthData indicates whether authentication-related data should be logged.
 		logAuthData bool
 
@@ -806,7 +803,7 @@ func (c *Client) SetSSLPort(ssl bool, fallback bool) {
 }
 
 // SetDebugLog sets or overrides whether the Client is using debug logging. The debug logger will log incoming
-// and outgoing communication between the Client and the server to os.Stderr.
+// and outgoing communication between the client and the server to log.Logger that is defined on the Client.
 //
 // Note: The SMTP communication might include unencrypted authentication data, depending on whether you are using
 // SMTP authentication and the type of authentication mechanism. This could pose a data protection risk. Use
@@ -815,9 +812,26 @@ func (c *Client) SetSSLPort(ssl bool, fallback bool) {
 // Parameters:
 //   - val: A boolean value indicating whether to enable (true) or disable (false) debug logging.
 func (c *Client) SetDebugLog(val bool) {
+	c.SetDebugLogWithSMTPClient(c.smtpClient, val)
+}
+
+// SetDebugLogWithSMTPClient sets or overrides whether the provided smtp.Client is using debug logging.
+// The debug logger will log incoming and outgoing communication between the client and the server to
+// log.Logger that is defined on the Client.
+//
+// Note: The SMTP communication might include unencrypted authentication data, depending on whether you are using
+// SMTP authentication and the type of authentication mechanism. This could pose a data protection risk. Use
+// debug logging with caution.
+//
+// Parameters:
+//   - client: A pointer to the smtp.Client that handles the connection to the server.
+//   - val: A boolean value indicating whether to enable (true) or disable (false) debug logging.
+func (c *Client) SetDebugLogWithSMTPClient(client *smtp.Client, val bool) {
+	c.mutex.Lock()
+	defer c.mutex.Unlock()
 	c.useDebugLog = val
-	if c.smtpClient != nil {
+	if client != nil {
-		c.smtpClient.SetDebugLog(val)
+		client.SetDebugLog(val)
 	}
 }
 
@@ -830,9 +844,24 @@ func (c *Client) SetDebugLog(val bool) {
 // Parameters:
 //   - logger: A logger that satisfies the log.Logger interface to be set for the Client.
 func (c *Client) SetLogger(logger log.Logger) {
+	c.SetLoggerWithSMTPClient(c.smtpClient, logger)
+}
+
+// SetLoggerWithSMTPClient sets or overrides the custom logger currently used by the provided smtp.Client.
+// The logger must satisfy the log.Logger interface and is only utilized when debug logging is enabled on
+// the provided smtp.Client.
+//
+// By default, log.Stdlog is used if no custom logger is provided.
+//
+// Parameters:
+//   - client: A pointer to the smtp.Client that handles the connection to the server.
+//   - logger: A logger that satisfies the log.Logger interface to be set for the Client.
+func (c *Client) SetLoggerWithSMTPClient(client *smtp.Client, logger log.Logger) {
+	c.mutex.Lock()
+	defer c.mutex.Unlock()
 	c.logger = logger
-	if c.smtpClient != nil {
+	if client != nil {
-		c.smtpClient.SetLogger(logger)
+		client.SetLogger(logger)
 	}
 }
 
@@ -926,67 +955,91 @@ func (c *Client) SetLogAuthData(logAuth bool) {
 // SMTP server.
 //
 // Parameters:
-//   - dialCtx: The context.Context used to control the connection timeout and cancellation.
+//   - ctxDial: The context.Context used to control the connection timeout and cancellation.
 //
 // Returns:
 //   - An error if the connection to the SMTP server fails or any subsequent command fails.
-func (c *Client) DialWithContext(dialCtx context.Context) error {
+func (c *Client) DialWithContext(ctxDial context.Context) error {
-	c.mutex.Lock()
+	client, err := c.DialToSMTPClientWithContext(ctxDial)
-	defer c.mutex.Unlock()
-
-	ctx, cancel := context.WithDeadline(dialCtx, time.Now().Add(c.connTimeout))
-	defer cancel()
-
-	if c.dialContextFunc == nil {
-		netDialer := net.Dialer{}
-		c.dialContextFunc = netDialer.DialContext
-
-		if c.useSSL {
-			tlsDialer := tls.Dialer{NetDialer: &netDialer, Config: c.tlsconfig}
-			c.isEncrypted = true
-			c.dialContextFunc = tlsDialer.DialContext
-		}
-	}
-	connection, err := c.dialContextFunc(ctx, "tcp", c.ServerAddr())
-	if err != nil && c.fallbackPort != 0 {
-		// TODO: should we somehow log or append the previous error?
-		connection, err = c.dialContextFunc(ctx, "tcp", c.serverFallbackAddr())
-	}
 	if err != nil {
 		return err
 	}
+	c.mutex.Lock()
+	c.smtpClient = client
+	c.mutex.Unlock()
+	return nil
+}
+
+// DialToSMTPClientWithContext establishes and configures a smtp.Client connection using
+// the provided context.
+//
+// This function uses the provided context to manage the connection deadline and cancellation.
+// It dials the SMTP server using the Client's configured DialContextFunc or a default dialer.
+// If SSL is enabled, it uses a TLS connection. After successfully connecting, it initializes
+// an smtp.Client, sends the HELO/EHLO command, and optionally performs STARTTLS and SMTP AUTH
+// based on the Client's configuration. Debug and authentication logging are enabled if
+// configured.
+//
+// Parameters:
+//   - ctxDial: The context used to control the connection timeout and cancellation.
+//
+// Returns:
+//   - A pointer to the initialized smtp.Client.
+//   - An error if the connection fails, the smtp.Client cannot be created, or any subsequent commands fail.
+func (c *Client) DialToSMTPClientWithContext(ctxDial context.Context) (*smtp.Client, error) {
+	c.mutex.RLock()
+	defer c.mutex.RUnlock()
+
+	ctx, cancel := context.WithDeadline(ctxDial, time.Now().Add(c.connTimeout))
+	defer cancel()
+
+	isEncrypted := false
+	dialContextFunc := c.dialContextFunc
+	if c.dialContextFunc == nil {
+		netDialer := net.Dialer{}
+		dialContextFunc = netDialer.DialContext
+		if c.useSSL {
+			tlsDialer := tls.Dialer{NetDialer: &netDialer, Config: c.tlsconfig}
+			isEncrypted = true
+			dialContextFunc = tlsDialer.DialContext
+		}
+	}
+	connection, err := dialContextFunc(ctx, "tcp", c.ServerAddr())
+	if err != nil && c.fallbackPort != 0 {
+		// TODO: should we somehow log or append the previous error?
+		connection, err = dialContextFunc(ctx, "tcp", c.serverFallbackAddr())
+	}
+	if err != nil {
+		return nil, err
+	}
 
 	client, err := smtp.NewClient(connection, c.host)
 	if err != nil {
-		return err
+		return nil, err
 	}
-	if client == nil {
-		return fmt.Errorf("SMTP client is nil")
-	}
-	c.smtpClient = client
 
 	if c.logger != nil {
-		c.smtpClient.SetLogger(c.logger)
+		client.SetLogger(c.logger)
 	}
 	if c.useDebugLog {
-		c.smtpClient.SetDebugLog(true)
+		client.SetDebugLog(true)
 	}
 	if c.logAuthData {
-		c.smtpClient.SetLogAuthData()
+		client.SetLogAuthData()
 	}
-	if err = c.smtpClient.Hello(c.helo); err != nil {
+	if err = client.Hello(c.helo); err != nil {
-		return err
+		return nil, err
 	}
 
-	if err = c.tls(); err != nil {
+	if err = c.tls(client, &isEncrypted); err != nil {
-		return err
+		return nil, err
 	}
 
-	if err = c.auth(); err != nil {
+	if err = c.auth(client, isEncrypted); err != nil {
-		return err
+		return nil, err
 	}
 
-	return nil
+	return client, nil
 }
 
 // Close terminates the connection to the SMTP server, returning an error if the disconnection
@@ -999,10 +1052,27 @@ func (c *Client) DialWithContext(dialCtx context.Context) error {
 // Returns:
 //   - An error if the disconnection fails; otherwise, returns nil.
 func (c *Client) Close() error {
-	if c.smtpClient == nil || !c.smtpClient.HasConnection() {
+	return c.CloseWithSMTPClient(c.smtpClient)
+}
+
+// CloseWithSMTPClient terminates the connection of the provided smtp.Client to the SMTP server,
+// returning an error if the disconnection fails. If the connection is already closed, this
+// method is a no-op and disregards any error.
+//
+// This function checks if the smtp.Client connection is active. If not, it simply returns
+// without any action. If the connection is active, it attempts to gracefully close the
+// connection using the Quit method.
+//
+// Parameters:
+//   - client: A pointer to the smtp.Client that handles the connection to the server.
+//
+// Returns:
+//   - An error if the disconnection fails; otherwise, returns nil.
+func (c *Client) CloseWithSMTPClient(client *smtp.Client) error {
+	if client == nil || !client.HasConnection() {
 		return nil
 	}
-	if err := c.smtpClient.Quit(); err != nil {
+	if err := client.Quit(); err != nil {
 		return fmt.Errorf("failed to close SMTP client: %w", err)
 	}
 
@@ -1016,12 +1086,29 @@ func (c *Client) Close() error {
 // the command fails, an error is returned.
 //
 // Returns:
-//   - An error if the connection check fails or if sending the RSET command fails; otherwise, returns nil.
+//   - An error if the connection check fails or if sending the RSET command fails;
+//     otherwise, returns nil.
 func (c *Client) Reset() error {
-	if err := c.checkConn(); err != nil {
+	return c.ResetWithSMTPClient(c.smtpClient)
+}
+
+// ResetWithSMTPClient sends an SMTP RSET command to the provided smtp.Client, to reset
+// the state of the current SMTP session.
+//
+// This method checks the connection to the SMTP server and, if the connection is valid,
+// it sends an RSET command to reset the session state. If the connection is invalid or
+// the command fails, an error is returned.
+//
+// Parameters:
+//   - client: A pointer to the smtp.Client that handles the connection to the server.
+//
+// Returns:
+//   - An error if the connection check fails or if sending the RSET command fails; otherwise, returns nil.
+func (c *Client) ResetWithSMTPClient(client *smtp.Client) error {
+	if err := c.checkConn(client); err != nil {
 		return err
 	}
-	if err := c.smtpClient.Reset(); err != nil {
+	if err := client.Reset(); err != nil {
 		return fmt.Errorf("failed to send RSET to SMTP client: %w", err)
 	}
 
@@ -1061,24 +1148,47 @@ func (c *Client) DialAndSend(messages ...*Msg) error {
 //   - An error if the connection fails, if sending the messages fails, or if closing the
 //     connection fails; otherwise, returns nil.
 func (c *Client) DialAndSendWithContext(ctx context.Context, messages ...*Msg) error {
-	c.sendMutex.Lock()
+	client, err := c.DialToSMTPClientWithContext(ctx)
-	defer c.sendMutex.Unlock()
+	if err != nil {
-	if err := c.DialWithContext(ctx); err != nil {
 		return fmt.Errorf("dial failed: %w", err)
 	}
 	defer func() {
-		_ = c.Close()
+		_ = c.CloseWithSMTPClient(client)
 	}()
 
-	if err := c.Send(messages...); err != nil {
+	if err = c.SendWithSMTPClient(client, messages...); err != nil {
 		return fmt.Errorf("send failed: %w", err)
 	}
-	if err := c.Close(); err != nil {
+	if err = c.CloseWithSMTPClient(client); err != nil {
 		return fmt.Errorf("failed to close connection: %w", err)
 	}
 	return nil
 }
 
+// Send attempts to send one or more Msg using the SMTP client that is assigned to the Client.
+// If the Client has no active connection to the server, Send will fail with an error. For
+// each of the provided Msg, it will associate a SendError with the Msg in case of a
+// transmission or delivery error.
+//
+// This method first checks for an active connection to the SMTP server. If the connection is
+// not valid, it returns a SendError. It then iterates over the provided messages, attempting
+// to send each one. If an error occurs during sending, the method records the error and
+// associates it with the corresponding Msg. If multiple errors are encountered, it aggregates
+// them into a single SendError to be returned.
+//
+// Parameters:
+//   - client: A pointer to the smtp.Client that holds the connection to the SMTP server
+//   - messages: A variadic list of pointers to Msg objects to be sent.
+//
+// Returns:
+//   - An error that represents the sending result, which may include multiple SendErrors if
+//     any occurred; otherwise, returns nil.
+func (c *Client) Send(messages ...*Msg) (returnErr error) {
+	c.sendMutex.Lock()
+	defer c.sendMutex.Unlock()
+	return c.SendWithSMTPClient(c.smtpClient, messages...)
+}
+
 // auth attempts to authenticate the client using SMTP AUTH mechanisms. It checks the connection,
 // determines the supported authentication methods, and applies the appropriate authentication
 // type. An error is returned if authentication fails.
@@ -1098,16 +1208,17 @@ func (c *Client) DialAndSendWithContext(ctx context.Context, messages ...*Msg) e
 // Returns:
 //   - An error if the connection check fails, if no supported authentication method is found,
 //     or if the authentication process fails.
-func (c *Client) auth() error {
+func (c *Client) auth(client *smtp.Client, isEnc bool) error {
+	var smtpAuth smtp.Auth
 	if c.smtpAuth == nil && c.smtpAuthType != SMTPAuthNoAuth {
-		hasSMTPAuth, smtpAuthType := c.smtpClient.Extension("AUTH")
+		hasSMTPAuth, smtpAuthType := client.Extension("AUTH")
 		if !hasSMTPAuth {
 			return fmt.Errorf("server does not support SMTP AUTH")
 		}
 
 		authType := c.smtpAuthType
 		if c.smtpAuthType == SMTPAuthAutoDiscover {
-			discoveredType, err := c.authTypeAutoDiscover(smtpAuthType)
+			discoveredType, err := c.authTypeAutoDiscover(smtpAuthType, isEnc)
 			if err != nil {
 				return err
 			}
@@ -1119,74 +1230,74 @@ func (c *Client) auth() error {
 			if !strings.Contains(smtpAuthType, string(SMTPAuthPlain)) {
 				return ErrPlainAuthNotSupported
 			}
-			c.smtpAuth = smtp.PlainAuth("", c.user, c.pass, c.host, false)
+			smtpAuth = smtp.PlainAuth("", c.user, c.pass, c.host, false)
 		case SMTPAuthPlainNoEnc:
 			if !strings.Contains(smtpAuthType, string(SMTPAuthPlain)) {
 				return ErrPlainAuthNotSupported
 			}
-			c.smtpAuth = smtp.PlainAuth("", c.user, c.pass, c.host, true)
+			smtpAuth = smtp.PlainAuth("", c.user, c.pass, c.host, true)
 		case SMTPAuthLogin:
 			if !strings.Contains(smtpAuthType, string(SMTPAuthLogin)) {
 				return ErrLoginAuthNotSupported
 			}
-			c.smtpAuth = smtp.LoginAuth(c.user, c.pass, c.host, false)
+			smtpAuth = smtp.LoginAuth(c.user, c.pass, c.host, false)
 		case SMTPAuthLoginNoEnc:
 			if !strings.Contains(smtpAuthType, string(SMTPAuthLogin)) {
 				return ErrLoginAuthNotSupported
 			}
-			c.smtpAuth = smtp.LoginAuth(c.user, c.pass, c.host, true)
+			smtpAuth = smtp.LoginAuth(c.user, c.pass, c.host, true)
 		case SMTPAuthCramMD5:
 			if !strings.Contains(smtpAuthType, string(SMTPAuthCramMD5)) {
 				return ErrCramMD5AuthNotSupported
 			}
-			c.smtpAuth = smtp.CRAMMD5Auth(c.user, c.pass)
+			smtpAuth = smtp.CRAMMD5Auth(c.user, c.pass)
 		case SMTPAuthXOAUTH2:
 			if !strings.Contains(smtpAuthType, string(SMTPAuthXOAUTH2)) {
 				return ErrXOauth2AuthNotSupported
 			}
-			c.smtpAuth = smtp.XOAuth2Auth(c.user, c.pass)
+			smtpAuth = smtp.XOAuth2Auth(c.user, c.pass)
 		case SMTPAuthSCRAMSHA1:
 			if !strings.Contains(smtpAuthType, string(SMTPAuthSCRAMSHA1)) {
 				return ErrSCRAMSHA1AuthNotSupported
 			}
-			c.smtpAuth = smtp.ScramSHA1Auth(c.user, c.pass)
+			smtpAuth = smtp.ScramSHA1Auth(c.user, c.pass)
 		case SMTPAuthSCRAMSHA256:
 			if !strings.Contains(smtpAuthType, string(SMTPAuthSCRAMSHA256)) {
 				return ErrSCRAMSHA256AuthNotSupported
 			}
-			c.smtpAuth = smtp.ScramSHA256Auth(c.user, c.pass)
+			smtpAuth = smtp.ScramSHA256Auth(c.user, c.pass)
 		case SMTPAuthSCRAMSHA1PLUS:
 			if !strings.Contains(smtpAuthType, string(SMTPAuthSCRAMSHA1PLUS)) {
 				return ErrSCRAMSHA1PLUSAuthNotSupported
 			}
-			tlsConnState, err := c.smtpClient.GetTLSConnectionState()
+			tlsConnState, err := client.GetTLSConnectionState()
 			if err != nil {
 				return err
 			}
-			c.smtpAuth = smtp.ScramSHA1PlusAuth(c.user, c.pass, tlsConnState)
+			smtpAuth = smtp.ScramSHA1PlusAuth(c.user, c.pass, tlsConnState)
 		case SMTPAuthSCRAMSHA256PLUS:
 			if !strings.Contains(smtpAuthType, string(SMTPAuthSCRAMSHA256PLUS)) {
 				return ErrSCRAMSHA256PLUSAuthNotSupported
 			}
-			tlsConnState, err := c.smtpClient.GetTLSConnectionState()
+			tlsConnState, err := client.GetTLSConnectionState()
 			if err != nil {
 				return err
 			}
-			c.smtpAuth = smtp.ScramSHA256PlusAuth(c.user, c.pass, tlsConnState)
+			smtpAuth = smtp.ScramSHA256PlusAuth(c.user, c.pass, tlsConnState)
 		default:
 			return fmt.Errorf("unsupported SMTP AUTH type %q", c.smtpAuthType)
 		}
 	}
 
-	if c.smtpAuth != nil {
+	if smtpAuth != nil {
-		if err := c.smtpClient.Auth(c.smtpAuth); err != nil {
+		if err := client.Auth(smtpAuth); err != nil {
 			return fmt.Errorf("SMTP AUTH failed: %w", err)
 		}
 	}
 	return nil
 }
 
-func (c *Client) authTypeAutoDiscover(supported string) (SMTPAuthType, error) {
+func (c *Client) authTypeAutoDiscover(supported string, isEnc bool) (SMTPAuthType, error) {
 	if supported == "" {
 		return "", ErrNoSupportedAuthDiscovered
 	}
@@ -1194,7 +1305,7 @@ func (c *Client) authTypeAutoDiscover(supported string) (SMTPAuthType, error) {
 		SMTPAuthSCRAMSHA256PLUS, SMTPAuthSCRAMSHA256, SMTPAuthSCRAMSHA1PLUS, SMTPAuthSCRAMSHA1,
 		SMTPAuthXOAUTH2, SMTPAuthCramMD5, SMTPAuthPlain, SMTPAuthLogin,
 	}
-	if !c.isEncrypted {
+	if !isEnc {
 		preferList = []SMTPAuthType{SMTPAuthSCRAMSHA256, SMTPAuthSCRAMSHA1, SMTPAuthXOAUTH2, SMTPAuthCramMD5}
 	}
 	mechs := strings.Split(supported, " ")
@@ -1231,13 +1342,13 @@ func sliceContains(slice []string, item string) bool {
 //
 // Returns:
 //   - An error if any part of the sending process fails; otherwise, returns nil.
-func (c *Client) sendSingleMsg(message *Msg) error {
+func (c *Client) sendSingleMsg(client *smtp.Client, message *Msg) error {
-	c.mutex.Lock()
+	c.mutex.RLock()
-	defer c.mutex.Unlock()
+	defer c.mutex.RUnlock()
-	escSupport, _ := c.smtpClient.Extension("ENHANCEDSTATUSCODES")
+	escSupport, _ := client.Extension("ENHANCEDSTATUSCODES")
 
 	if message.encoding == NoEncoding {
-		if ok, _ := c.smtpClient.Extension("8BITMIME"); !ok {
+		if ok, _ := client.Extension("8BITMIME"); !ok {
 			return &SendError{Reason: ErrNoUnencoded, isTemp: false, affectedMsg: message}
 		}
 	}
@@ -1260,16 +1371,16 @@ func (c *Client) sendSingleMsg(message *Msg) error {
 
 	if c.requestDSN {
 		if c.dsnReturnType != "" {
-			c.smtpClient.SetDSNMailReturnOption(string(c.dsnReturnType))
+			client.SetDSNMailReturnOption(string(c.dsnReturnType))
 		}
 	}
-	if err = c.smtpClient.Mail(from); err != nil {
+	if err = client.Mail(from); err != nil {
 		retError := &SendError{
 			Reason: ErrSMTPMailFrom, errlist: []error{err}, isTemp: isTempError(err),
 			affectedMsg: message, errcode: errorCode(err),
 			enhancedStatusCode: enhancedStatusCode(err, escSupport),
 		}
-		if resetSendErr := c.smtpClient.Reset(); resetSendErr != nil {
+		if resetSendErr := client.Reset(); resetSendErr != nil {
 			retError.errlist = append(retError.errlist, resetSendErr)
 		}
 		return retError
@@ -1279,9 +1390,9 @@ func (c *Client) sendSingleMsg(message *Msg) error {
 	rcptSendErr.errlist = make([]error, 0)
 	rcptSendErr.rcpt = make([]string, 0)
 	rcptNotifyOpt := strings.Join(c.dsnRcptNotifyType, ",")
-	c.smtpClient.SetDSNRcptNotifyOption(rcptNotifyOpt)
+	client.SetDSNRcptNotifyOption(rcptNotifyOpt)
 	for _, rcpt := range rcpts {
-		if err = c.smtpClient.Rcpt(rcpt); err != nil {
+		if err = client.Rcpt(rcpt); err != nil {
 			rcptSendErr.Reason = ErrSMTPRcptTo
 			rcptSendErr.errlist = append(rcptSendErr.errlist, err)
 			rcptSendErr.rcpt = append(rcptSendErr.rcpt, rcpt)
@@ -1292,12 +1403,12 @@ func (c *Client) sendSingleMsg(message *Msg) error {
 		}
 	}
 	if hasError {
-		if resetSendErr := c.smtpClient.Reset(); resetSendErr != nil {
+		if resetSendErr := client.Reset(); resetSendErr != nil {
 			rcptSendErr.errlist = append(rcptSendErr.errlist, resetSendErr)
 		}
 		return rcptSendErr
 	}
-	writer, err := c.smtpClient.Data()
+	writer, err := client.Data()
 	if err != nil {
 		return &SendError{
 			Reason: ErrSMTPData, errlist: []error{err}, isTemp: isTempError(err),
@@ -1322,7 +1433,7 @@ func (c *Client) sendSingleMsg(message *Msg) error {
 	}
 	message.isDelivered = true
 
-	if err = c.Reset(); err != nil {
+	if err = c.ResetWithSMTPClient(client); err != nil {
 		return &SendError{
 			Reason: ErrSMTPReset, errlist: []error{err}, isTemp: isTempError(err),
 			affectedMsg: message, errcode: errorCode(err),
@@ -1344,21 +1455,24 @@ func (c *Client) sendSingleMsg(message *Msg) error {
 // Returns:
 //   - An error if there is no active connection, if the NOOP command fails, or if extending
 //     the deadline fails; otherwise, returns nil.
-func (c *Client) checkConn() error {
+func (c *Client) checkConn(client *smtp.Client) error {
-	if c.smtpClient == nil {
+	if client == nil {
 		return ErrNoActiveConnection
 	}
-	if !c.smtpClient.HasConnection() {
+	if !client.HasConnection() {
 		return ErrNoActiveConnection
 	}
 
-	if !c.noNoop {
+	c.mutex.RLock()
-		if err := c.smtpClient.Noop(); err != nil {
+	noNoop := c.noNoop
+	c.mutex.RUnlock()
+	if !noNoop {
+		if err := client.Noop(); err != nil {
 			return ErrNoActiveConnection
 		}
 	}
 
-	if err := c.smtpClient.UpdateDeadline(c.connTimeout); err != nil {
+	if err := client.UpdateDeadline(c.connTimeout); err != nil {
 		return ErrDeadlineExtendFailed
 	}
 	return nil
@@ -1405,10 +1519,10 @@ func (c *Client) setDefaultHelo() error {
 // Returns:
 //   - An error if there is no active connection, if STARTTLS is required but not supported,
 //     or if there are issues during the TLS handshake; otherwise, returns nil.
-func (c *Client) tls() error {
+func (c *Client) tls(client *smtp.Client, isEnc *bool) error {
 	if !c.useSSL && c.tlspolicy != NoTLS {
 		hasStartTLS := false
-		extension, _ := c.smtpClient.Extension("STARTTLS")
+		extension, _ := client.Extension("STARTTLS")
 		if c.tlspolicy == TLSMandatory {
 			hasStartTLS = true
 			if !extension {
@@ -1422,21 +1536,21 @@ func (c *Client) tls() error {
 			}
 		}
 		if hasStartTLS {
-			if err := c.smtpClient.StartTLS(c.tlsconfig); err != nil {
+			if err := client.StartTLS(c.tlsconfig); err != nil {
 				return err
 			}
 		}
-		tlsConnState, err := c.smtpClient.GetTLSConnectionState()
+		tlsConnState, err := client.GetTLSConnectionState()
 		if err != nil {
 			switch {
 			case errors.Is(err, smtp.ErrNonTLSConnection):
-				c.isEncrypted = false
+				*isEnc = false
 				return nil
 			default:
 				return fmt.Errorf("failed to get TLS connection state: %w", err)
 			}
 		}
-		c.isEncrypted = tlsConnState.HandshakeComplete
+		*isEnc = tlsConnState.HandshakeComplete
 	}
 	return nil
 }

client_119.go

@@ -7,12 +7,16 @@
 
 package mail
 
-import "errors"
+import (
+	"errors"
 
-// Send attempts to send one or more Msg using the Client connection to the SMTP server.
+	"github.com/wneessen/go-mail/smtp"
-// If the Client has no active connection to the server, Send will fail with an error. For each
+)
-// of the provided Msg, it will associate a SendError with the Msg in case of a transmission
+
-// or delivery error.
+// SendWithSMTPClient attempts to send one or more Msg using a provided smtp.Client with an
+// established connection to the SMTP server. If the smtp.Client has no active connection to
+// the server, SendWithSMTPClient will fail with an error. For each of the provided Msg, it
+// will associate a SendError with the Msg in case of a transmission or delivery error.
 //
 // This method first checks for an active connection to the SMTP server. If the connection is
 // not valid, it returns a SendError. It then iterates over the provided messages, attempting
@@ -21,17 +25,18 @@ import "errors"
 // them into a single SendError to be returned.
 //
 // Parameters:
+//   - client: A pointer to the smtp.Client that holds the connection to the SMTP server
 //   - messages: A variadic list of pointers to Msg objects to be sent.
 //
 // Returns:
 //   - An error that represents the sending result, which may include multiple SendErrors if
 //     any occurred; otherwise, returns nil.
-func (c *Client) Send(messages ...*Msg) error {
+func (c *Client) SendWithSMTPClient(client *smtp.Client, messages ...*Msg) error {
 	escSupport := false
-	if c.smtpClient != nil {
+	if client != nil {
-		escSupport, _ = c.smtpClient.Extension("ENHANCEDSTATUSCODES")
+		escSupport, _ = client.Extension("ENHANCEDSTATUSCODES")
 	}
-	if err := c.checkConn(); err != nil {
+	if err := c.checkConn(client); err != nil {
 		return &SendError{
 			Reason: ErrConnCheck, errlist: []error{err}, isTemp: isTempError(err),
 			errcode: errorCode(err), enhancedStatusCode: enhancedStatusCode(err, escSupport),
@@ -39,7 +44,7 @@ func (c *Client) Send(messages ...*Msg) error {
 	}
 	var errs []*SendError
 	for id, message := range messages {
-		if sendErr := c.sendSingleMsg(message); sendErr != nil {
+		if sendErr := c.sendSingleMsg(client, message); sendErr != nil {
 			messages[id].sendError = sendErr
 
 			var msgSendErr *SendError

client_120.go

@@ -9,29 +9,34 @@ package mail
 
 import (
 	"errors"
+
+	"github.com/wneessen/go-mail/smtp"
 )
 
-// Send attempts to send one or more Msg using the Client connection to the SMTP server.
+// SendWithSMTPClient attempts to send one or more Msg using a provided smtp.Client with an
-// If the Client has no active connection to the server, Send will fail with an error. For each
+// established connection to the SMTP server. If the smtp.Client has no active connection to
-// of the provided Msg, it will associate a SendError with the Msg in case of a transmission
+// the server, SendWithSMTPClient will fail with an error. For each of the provided Msg, it
-// or delivery error.
+// will associate a SendError with the Msg in case of a transmission or delivery error.
 //
 // This method first checks for an active connection to the SMTP server. If the connection is
-// not valid, it returns an error wrapped in a SendError. It then iterates over the provided
+// not valid, it returns a SendError. It then iterates over the provided messages, attempting
-// messages, attempting to send each one. If an error occurs during sending, the method records
+// to send each one. If an error occurs during sending, the method records the error and
-// the error and associates it with the corresponding Msg.
+// associates it with the corresponding Msg. If multiple errors are encountered, it aggregates
+// them into a single SendError to be returned.
 //
 // Parameters:
+//   - client: A pointer to the smtp.Client that holds the connection to the SMTP server
 //   - messages: A variadic list of pointers to Msg objects to be sent.
 //
 // Returns:
-//   - An error that aggregates any SendErrors encountered during the sending process; otherwise, returns nil.
+//   - An error that represents the sending result, which may include multiple SendErrors if
-func (c *Client) Send(messages ...*Msg) (returnErr error) {
+//     any occurred; otherwise, returns nil.
+func (c *Client) SendWithSMTPClient(client *smtp.Client, messages ...*Msg) (returnErr error) {
 	escSupport := false
-	if c.smtpClient != nil {
+	if client != nil {
-		escSupport, _ = c.smtpClient.Extension("ENHANCEDSTATUSCODES")
+		escSupport, _ = client.Extension("ENHANCEDSTATUSCODES")
 	}
-	if err := c.checkConn(); err != nil {
+	if err := c.checkConn(client); err != nil {
 		returnErr = &SendError{
 			Reason: ErrConnCheck, errlist: []error{err}, isTemp: isTempError(err),
 			errcode: errorCode(err), enhancedStatusCode: enhancedStatusCode(err, escSupport),
@@ -45,7 +50,7 @@ func (c *Client) Send(messages ...*Msg) (returnErr error) {
 	}()
 
 	for id, message := range messages {
-		if sendErr := c.sendSingleMsg(message); sendErr != nil {
+		if sendErr := c.sendSingleMsg(client, message); sendErr != nil {
 			messages[id].sendError = sendErr
 			errs = append(errs, sendErr)
 		}

client_test.go

@@ -1772,11 +1772,8 @@ func TestClient_DialWithContext(t *testing.T) {
 				t.Errorf("failed to close the client: %s", err)
 			}
 		})
-		if client.smtpClient == nil {
+		if client.smtpClient != nil {
-			t.Errorf("client with invalid HELO should still have a smtp client, got nil")
+			t.Error("client with invalid HELO should not have a smtp client")
-		}
-		if !client.smtpClient.HasConnection() {
-			t.Errorf("client with invalid HELO should still have a smtp client connection, got nil")
 		}
 	})
 	t.Run("fail on base port and fallback", func(t *testing.T) {
@@ -1825,11 +1822,8 @@ func TestClient_DialWithContext(t *testing.T) {
 		if err = client.DialWithContext(ctxDial); err == nil {
 			t.Fatalf("connection was supposed to fail, but didn't")
 		}
-		if client.smtpClient == nil {
+		if client.smtpClient != nil {
-			t.Fatalf("client has no smtp client")
+			t.Fatalf("client is not supposed to have a smtp client")
-		}
-		if !client.smtpClient.HasConnection() {
-			t.Errorf("client has no connection")
 		}
 	})
 	t.Run("connect with failing auth", func(t *testing.T) {
@@ -2297,6 +2291,7 @@ func TestClient_DialAndSendWithContext(t *testing.T) {
 			t.Errorf("client was supposed to fail on dial")
 		}
 	})
+	// https://github.com/wneessen/go-mail/issues/380
 	t.Run("concurrent sending via DialAndSendWithContext", func(t *testing.T) {
 		ctx, cancel := context.WithCancel(context.Background())
 		defer cancel()
@@ -2336,6 +2331,44 @@ func TestClient_DialAndSendWithContext(t *testing.T) {
 		}
 		wg.Wait()
 	})
+	// https://github.com/wneessen/go-mail/issues/385
+	t.Run("concurrent sending via DialAndSendWithContext on receiver func", func(t *testing.T) {
+		ctx, cancel := context.WithCancel(context.Background())
+		defer cancel()
+		PortAdder.Add(1)
+		serverPort := int(TestServerPortBase + PortAdder.Load())
+		featureSet := "250-8BITMIME\r\n250-DSN\r\n250 SMTPUTF8"
+		go func() {
+			if err := simpleSMTPServer(ctx, t, &serverProps{
+				FeatureSet: featureSet,
+				ListenPort: serverPort,
+			}); err != nil {
+				t.Errorf("failed to start test server: %s", err)
+				return
+			}
+		}()
+		time.Sleep(time.Millisecond * 30)
+
+		client, err := NewClient(DefaultHost, WithPort(serverPort), WithTLSPolicy(NoTLS))
+		if err != nil {
+			t.Fatalf("failed to create new client: %s", err)
+		}
+		sender := testSender{client}
+
+		ctxDial := context.Background()
+		wg := sync.WaitGroup{}
+		for i := 0; i < 5; i++ {
+			wg.Add(1)
+			msg := testMessage(t)
+			go func() {
+				defer wg.Done()
+				if goroutineErr := sender.Send(ctxDial, msg); goroutineErr != nil {
+					t.Errorf("failed to send message: %s", goroutineErr)
+				}
+			}()
+		}
+		wg.Wait()
+	})
 }
 
 func TestClient_auth(t *testing.T) {
@@ -2574,8 +2607,8 @@ func TestClient_authTypeAutoDiscover(t *testing.T) {
 	}
 	for _, tt := range tests {
 		t.Run("AutoDiscover selects the strongest auth type: "+string(tt.expect), func(t *testing.T) {
-			client := &Client{smtpAuthType: SMTPAuthAutoDiscover, isEncrypted: tt.tls}
+			client := &Client{smtpAuthType: SMTPAuthAutoDiscover}
-			authType, err := client.authTypeAutoDiscover(tt.supported)
+			authType, err := client.authTypeAutoDiscover(tt.supported, tt.tls)
 			if err != nil && !tt.shouldFail {
 				t.Fatalf("failed to auto discover auth type: %s", err)
 			}
@@ -2709,6 +2742,82 @@ func TestClient_Send(t *testing.T) {
 	})
 }
 
+func TestClient_DialToSMTPClientWithContext(t *testing.T) {
+	t.Run("establish a new client connection", func(t *testing.T) {
+		ctx, cancel := context.WithCancel(context.Background())
+		defer cancel()
+		PortAdder.Add(1)
+		serverPort := int(TestServerPortBase + PortAdder.Load())
+		featureSet := "250-8BITMIME\r\n250-DSN\r\n250 SMTPUTF8"
+		go func() {
+			if err := simpleSMTPServer(ctx, t, &serverProps{
+				FeatureSet: featureSet,
+				ListenPort: serverPort,
+			}); err != nil {
+				t.Errorf("failed to start test server: %s", err)
+				return
+			}
+		}()
+		time.Sleep(time.Millisecond * 30)
+
+		ctxDial, cancelDial := context.WithTimeout(ctx, time.Millisecond*500)
+		t.Cleanup(cancelDial)
+
+		client, err := NewClient(DefaultHost, WithPort(serverPort), WithTLSPolicy(NoTLS))
+		if err != nil {
+			t.Fatalf("failed to create new client: %s", err)
+		}
+		smtpClient, err := client.DialToSMTPClientWithContext(ctxDial)
+		if err != nil {
+			var netErr net.Error
+			if errors.As(err, &netErr) && netErr.Timeout() {
+				t.Skip("failed to connect to the test server due to timeout")
+			}
+			t.Fatalf("failed to connect to test server: %s", err)
+		}
+		t.Cleanup(func() {
+			if err := client.CloseWithSMTPClient(smtpClient); err != nil {
+				var netErr net.Error
+				if errors.As(err, &netErr) && netErr.Timeout() {
+					t.Skip("failed to close the test server connection due to timeout")
+				}
+				t.Errorf("failed to close client: %s", err)
+			}
+		})
+		if smtpClient == nil {
+			t.Fatal("expected SMTP client, got nil")
+		}
+		if !smtpClient.HasConnection() {
+			t.Fatal("expected connection on smtp client")
+		}
+		if ok, _ := smtpClient.Extension("DSN"); !ok {
+			t.Error("expected DSN extension but it was not found")
+		}
+	})
+	t.Run("dial to SMTP server fails on first client writeFile", func(t *testing.T) {
+		var fake faker
+		fake.ReadWriter = struct {
+			io.Reader
+			io.Writer
+		}{
+			failReadWriteSeekCloser{},
+			failReadWriteSeekCloser{},
+		}
+
+		ctxDial, cancelDial := context.WithTimeout(context.Background(), time.Millisecond*500)
+		t.Cleanup(cancelDial)
+
+		client, err := NewClient(DefaultHost, WithDialContextFunc(getFakeDialFunc(fake)))
+		if err != nil {
+			t.Fatalf("failed to create new client: %s", err)
+		}
+		_, err = client.DialToSMTPClientWithContext(ctxDial)
+		if err == nil {
+			t.Fatal("expected connection to fake to fail")
+		}
+	})
+}
+
 func TestClient_sendSingleMsg(t *testing.T) {
 	t.Run("connect and send email", func(t *testing.T) {
 		ctx, cancel := context.WithCancel(context.Background())
@@ -2748,7 +2857,7 @@ func TestClient_sendSingleMsg(t *testing.T) {
 				t.Errorf("failed to close client: %s", err)
 			}
 		})
-		if err = client.sendSingleMsg(message); err != nil {
+		if err = client.sendSingleMsg(client.smtpClient, message); err != nil {
 			t.Errorf("failed to send message: %s", err)
 		}
 	})
@@ -2791,7 +2900,7 @@ func TestClient_sendSingleMsg(t *testing.T) {
 				t.Errorf("failed to close client: %s", err)
 			}
 		})
-		if err = client.sendSingleMsg(message); err == nil {
+		if err = client.sendSingleMsg(client.smtpClient, message); err == nil {
 			t.Errorf("client should have failed to send message")
 		}
 	})
@@ -2836,7 +2945,7 @@ func TestClient_sendSingleMsg(t *testing.T) {
 				t.Errorf("failed to close client: %s", err)
 			}
 		})
-		if err = client.sendSingleMsg(message); err == nil {
+		if err = client.sendSingleMsg(client.smtpClient, message); err == nil {
 			t.Errorf("client should have failed to send message")
 		}
 		var sendErr *SendError
@@ -2886,7 +2995,7 @@ func TestClient_sendSingleMsg(t *testing.T) {
 				t.Errorf("failed to close client: %s", err)
 			}
 		})
-		if err = client.sendSingleMsg(message); err == nil {
+		if err = client.sendSingleMsg(client.smtpClient, message); err == nil {
 			t.Errorf("client should have failed to send message")
 		}
 		var sendErr *SendError
@@ -2936,7 +3045,7 @@ func TestClient_sendSingleMsg(t *testing.T) {
 				t.Errorf("failed to close client: %s", err)
 			}
 		})
-		if err = client.sendSingleMsg(message); err == nil {
+		if err = client.sendSingleMsg(client.smtpClient, message); err == nil {
 			t.Errorf("client should have failed to send message")
 		}
 		var sendErr *SendError
@@ -2986,7 +3095,7 @@ func TestClient_sendSingleMsg(t *testing.T) {
 				t.Errorf("failed to close client: %s", err)
 			}
 		})
-		if err = client.sendSingleMsg(message); err != nil {
+		if err = client.sendSingleMsg(client.smtpClient, message); err != nil {
 			t.Errorf("failed to send message: %s", err)
 		}
 	})
@@ -3029,7 +3138,7 @@ func TestClient_sendSingleMsg(t *testing.T) {
 				t.Errorf("failed to close client: %s", err)
 			}
 		})
-		if err = client.sendSingleMsg(message); err == nil {
+		if err = client.sendSingleMsg(client.smtpClient, message); err == nil {
 			t.Errorf("client should have failed to send message")
 		}
 		var sendErr *SendError
@@ -3080,7 +3189,7 @@ func TestClient_sendSingleMsg(t *testing.T) {
 				t.Errorf("failed to close client: %s", err)
 			}
 		})
-		if err = client.sendSingleMsg(message); err == nil {
+		if err = client.sendSingleMsg(client.smtpClient, message); err == nil {
 			t.Errorf("client should have failed to send message")
 		}
 		var sendErr *SendError
@@ -3131,7 +3240,7 @@ func TestClient_sendSingleMsg(t *testing.T) {
 				t.Errorf("failed to close client: %s", err)
 			}
 		})
-		if err = client.sendSingleMsg(message); err == nil {
+		if err = client.sendSingleMsg(client.smtpClient, message); err == nil {
 			t.Errorf("client should have failed to send message")
 		}
 		var sendErr *SendError
@@ -3181,7 +3290,7 @@ func TestClient_sendSingleMsg(t *testing.T) {
 				t.Errorf("failed to close client: %s", err)
 			}
 		})
-		if err = client.sendSingleMsg(message); err == nil {
+		if err = client.sendSingleMsg(client.smtpClient, message); err == nil {
 			t.Errorf("client should have failed to send message")
 		}
 		var sendErr *SendError
@@ -3231,7 +3340,7 @@ func TestClient_sendSingleMsg(t *testing.T) {
 				t.Errorf("failed to close client: %s", err)
 			}
 		})
-		if err = client.sendSingleMsg(message); err == nil {
+		if err = client.sendSingleMsg(client.smtpClient, message); err == nil {
 			t.Errorf("client should have failed to send message")
 		}
 		var sendErr *SendError
@@ -3281,7 +3390,7 @@ func TestClient_sendSingleMsg(t *testing.T) {
 				t.Errorf("failed to close client: %s", err)
 			}
 		})
-		if err = client.sendSingleMsg(message); err == nil {
+		if err = client.sendSingleMsg(client.smtpClient, message); err == nil {
 			t.Error("expected mail delivery to fail")
 		}
 		var sendErr *SendError
@@ -3334,7 +3443,7 @@ func TestClient_checkConn(t *testing.T) {
 				t.Errorf("failed to close client: %s", err)
 			}
 		})
-		if err = client.checkConn(); err != nil {
+		if err = client.checkConn(client.smtpClient); err != nil {
 			t.Errorf("failed to check connection: %s", err)
 		}
 	})
@@ -3375,7 +3484,7 @@ func TestClient_checkConn(t *testing.T) {
 				t.Errorf("failed to close client: %s", err)
 			}
 		})
-		if err = client.checkConn(); err == nil {
+		if err = client.checkConn(client.smtpClient); err == nil {
 			t.Errorf("client should have failed on connection check")
 		}
 		if !errors.Is(err, ErrNoActiveConnection) {
@@ -3387,7 +3496,7 @@ func TestClient_checkConn(t *testing.T) {
 		if err != nil {
 			t.Fatalf("failed to create new client: %s", err)
 		}
-		if err = client.checkConn(); err == nil {
+		if err = client.checkConn(client.smtpClient); err == nil {
 			t.Errorf("client should have failed on connection check")
 		}
 		if !errors.Is(err, ErrNoActiveConnection) {
@@ -3611,24 +3720,20 @@ func TestClient_XOAuth2OnFaker(t *testing.T) {
 		}
 		if err = c.DialWithContext(context.Background()); err == nil {
 			t.Fatal("expected dial error got nil")
-		} else {
+		}
-			if !errors.Is(err, ErrXOauth2AuthNotSupported) {
+		if !errors.Is(err, ErrXOauth2AuthNotSupported) {
-				t.Fatalf("expected %v; got %v", ErrXOauth2AuthNotSupported, err)
+			t.Fatalf("expected %v; got %v", ErrXOauth2AuthNotSupported, err)
-			}
 		}
 		if err = c.Close(); err != nil {
 			t.Fatalf("disconnect from test server failed: %v", err)
 		}
 		client := strings.Split(wrote.String(), "\r\n")
-		if len(client) != 3 {
+		if len(client) != 2 {
-			t.Fatalf("unexpected number of client requests got %d; want 3", len(client))
+			t.Fatalf("unexpected number of client requests got %d; want 2", len(client))
 		}
 		if !strings.HasPrefix(client[0], "EHLO") {
 			t.Fatalf("expected EHLO, got %q", client[0])
 		}
-		if client[1] != "QUIT" {
-			t.Fatalf("expected QUIT, got %q", client[3])
-		}
 	})
 }
 
@@ -3652,6 +3757,17 @@ func (f faker) SetDeadline(time.Time) error      { return nil }
 func (f faker) SetReadDeadline(time.Time) error  { return nil }
 func (f faker) SetWriteDeadline(time.Time) error { return nil }
 
+type testSender struct {
+	client *Client
+}
+
+func (t *testSender) Send(ctx context.Context, m *Msg) error {
+	if err := t.client.DialAndSendWithContext(ctx, m); err != nil {
+		return fmt.Errorf("failed to dial and send mail: %w", err)
+	}
+	return nil
+}
+
 // parseJSONLog parses a JSON encoded log from the provided buffer and returns a slice of logLine structs.
 // In case of a decode error, it reports the error to the testing framework.
 func parseJSONLog(t *testing.T, buf *bytes.Buffer) logData {

smtp/smtp.go

@@ -601,12 +601,16 @@ func (c *Client) SetLogAuthData() {
 
 // SetDSNMailReturnOption sets the DSN mail return option for the Mail method
 func (c *Client) SetDSNMailReturnOption(d string) {
+	c.mutex.Lock()
 	c.dsnmrtype = d
+	c.mutex.Unlock()
 }
 
 // SetDSNRcptNotifyOption sets the DSN recipient notify option for the Mail method
 func (c *Client) SetDSNRcptNotifyOption(d string) {
+	c.mutex.Lock()
 	c.dsnrntype = d
+	c.mutex.Unlock()
 }
 
 // HasConnection checks if the client has an active connection.