Merge pull request #91 from wneessen/feature/90_provide-a-way-of-knowing-which-emails-failedsucceeded-in-sending

Introduction of new error type for sending errors

client_119.go

@@ -7,89 +7,118 @@
 
 package mail
 
-import (
-	"fmt"
-)
-
 // Send sends out the mail message
 func (c *Client) Send(ml ...*Msg) error {
-	var errs []error
+	if cerr := c.checkConn(); cerr != nil {
-	if err := c.checkConn(); err != nil {
+		return &SendError{Reason: ErrConnCheck, errlist: []error{cerr}, isTemp: isTempError(cerr)}
-		return fmt.Errorf("failed to send mail: %w", err)
 	}
+	var errs []*SendError
 	for _, m := range ml {
+		m.sendError = nil
 		if m.encoding == NoEncoding {
 			if ok, _ := c.sc.Extension("8BITMIME"); !ok {
-				errs = append(errs, ErrServerNoUnencoded)
+				se := &SendError{Reason: ErrNoUnencoded, isTemp: false}
+				m.sendError = se
+				errs = append(errs, se)
 				continue
 			}
 		}
 		f, err := m.GetSender(false)
 		if err != nil {
-			errs = append(errs, err)
+			se := &SendError{Reason: ErrGetSender, errlist: []error{err}, isTemp: isTempError(err)}
+			m.sendError = se
+			errs = append(errs, se)
 			continue
 		}
 		rl, err := m.GetRecipients()
 		if err != nil {
-			errs = append(errs, err)
+			se := &SendError{Reason: ErrGetRcpts, errlist: []error{err}, isTemp: isTempError(err)}
+			m.sendError = se
+			errs = append(errs, se)
 			continue
 		}
 
 		if err := c.mail(f); err != nil {
-			errs = append(errs, fmt.Errorf("sending MAIL FROM command failed: %w", err))
+			se := &SendError{Reason: ErrSMTPMailFrom, errlist: []error{err}, isTemp: isTempError(err)}
 			if reserr := c.sc.Reset(); reserr != nil {
-				errs = append(errs, reserr)
+				se.errlist = append(se.errlist, reserr)
 			}
+			m.sendError = se
+			errs = append(errs, se)
 			continue
 		}
 		failed := false
+		rse := &SendError{}
+		rse.errlist = make([]error, 0)
+		rse.rcpt = make([]string, 0)
 		for _, r := range rl {
 			if err := c.rcpt(r); err != nil {
-				errs = append(errs, fmt.Errorf("sending RCPT TO command failed: %w", err))
+				rse.Reason = ErrSMTPRcptTo
+				rse.errlist = append(rse.errlist, err)
+				rse.rcpt = append(rse.rcpt, r)
+				rse.isTemp = isTempError(err)
 				failed = true
 			}
 		}
 		if failed {
 			if reserr := c.sc.Reset(); reserr != nil {
-				errs = append(errs, reserr)
+				rse.errlist = append(rse.errlist, err)
 			}
+			m.sendError = rse
+			errs = append(errs, rse)
 			continue
 		}
 		w, err := c.sc.Data()
 		if err != nil {
-			errs = append(errs, fmt.Errorf("sending DATA command failed: %w", err))
+			se := &SendError{Reason: ErrSMTPData, errlist: []error{err}, isTemp: isTempError(err)}
+			m.sendError = se
+			errs = append(errs, se)
 			continue
 		}
 		_, err = m.WriteTo(w)
 		if err != nil {
-			errs = append(errs, fmt.Errorf("sending mail content failed: %w", err))
+			se := &SendError{Reason: ErrWriteContent, errlist: []error{err}, isTemp: isTempError(err)}
+			m.sendError = se
+			errs = append(errs, se)
 			continue
 		}
 
 		if err := w.Close(); err != nil {
-			errs = append(errs, fmt.Errorf("failed to close DATA writer: %w", err))
+			se := &SendError{Reason: ErrSMTPDataClose, errlist: []error{err}, isTemp: isTempError(err)}
+			m.sendError = se
+			errs = append(errs, se)
 			continue
 		}
 
 		if err := c.Reset(); err != nil {
-			errs = append(errs, fmt.Errorf("sending RSET command failed: %w", err))
+			se := &SendError{Reason: ErrSMTPReset, errlist: []error{err}, isTemp: isTempError(err)}
+			m.sendError = se
+			errs = append(errs, se)
 			continue
 		}
 		if err := c.checkConn(); err != nil {
-			errs = append(errs, fmt.Errorf("failed to check server connection: %w", err))
+			se := &SendError{Reason: ErrConnCheck, errlist: []error{err}, isTemp: isTempError(err)}
+			m.sendError = se
+			errs = append(errs, se)
 			continue
 		}
 	}
 
 	if len(errs) > 0 {
-		errtxt := ""
+		if len(errs) > 1 {
+			re := &SendError{Reason: ErrAmbiguous}
 			for i := range errs {
-			errtxt += fmt.Sprintf("%s", errs[i])
+				re.errlist = append(re.errlist, errs[i].errlist...)
-			if i < len(errs) {
+				re.rcpt = append(re.rcpt, errs[i].rcpt...)
-				errtxt += "\n"
 			}
+
+			// We assume that the isTemp flag from the last error we received should be the
+			// indicator for the returned isTemp flag as well
+			re.isTemp = errs[len(errs)-1].isTemp
+
+			return re
 		}
-		return fmt.Errorf("%s", errtxt)
+		return errs[0]
 	}
 	return nil
 }

client_120.go

@@ -9,44 +9,54 @@ package mail
 
 import (
 	"errors"
-	"fmt"
 )
 
 // Send sends out the mail message
 func (c *Client) Send(ml ...*Msg) (rerr error) {
 	if err := c.checkConn(); err != nil {
-		rerr = fmt.Errorf("failed to send mail: %w", err)
+		rerr = &SendError{Reason: ErrConnCheck, errlist: []error{err}, isTemp: isTempError(err)}
 		return
 	}
 	for _, m := range ml {
+		m.sendError = nil
 		if m.encoding == NoEncoding {
 			if ok, _ := c.sc.Extension("8BITMIME"); !ok {
-				rerr = errors.Join(rerr, ErrServerNoUnencoded)
+				m.sendError = &SendError{Reason: ErrNoUnencoded, isTemp: false}
+				rerr = errors.Join(rerr, m.sendError)
 				continue
 			}
 		}
 		f, err := m.GetSender(false)
 		if err != nil {
-			rerr = errors.Join(rerr, err)
+			m.sendError = &SendError{Reason: ErrGetSender, errlist: []error{err}, isTemp: isTempError(err)}
+			rerr = errors.Join(rerr, m.sendError)
 			continue
 		}
 		rl, err := m.GetRecipients()
 		if err != nil {
-			rerr = errors.Join(rerr, err)
+			m.sendError = &SendError{Reason: ErrGetRcpts, errlist: []error{err}, isTemp: isTempError(err)}
+			rerr = errors.Join(rerr, m.sendError)
 			continue
 		}
 
 		if err := c.mail(f); err != nil {
-			rerr = errors.Join(rerr, fmt.Errorf("sending MAIL FROM command failed: %w", err))
+			m.sendError = &SendError{Reason: ErrSMTPMailFrom, errlist: []error{err}, isTemp: isTempError(err)}
+			rerr = errors.Join(rerr, m.sendError)
 			if reserr := c.sc.Reset(); reserr != nil {
 				rerr = errors.Join(rerr, reserr)
 			}
 			continue
 		}
 		failed := false
+		rse := &SendError{}
+		rse.errlist = make([]error, 0)
+		rse.rcpt = make([]string, 0)
 		for _, r := range rl {
 			if err := c.rcpt(r); err != nil {
-				rerr = errors.Join(rerr, fmt.Errorf("sending RCPT TO command failed: %w", err))
+				rse.Reason = ErrSMTPRcptTo
+				rse.errlist = append(rse.errlist, err)
+				rse.rcpt = append(rse.rcpt, r)
+				rse.isTemp = isTempError(err)
 				failed = true
 			}
 		}
@@ -54,30 +64,37 @@ func (c *Client) Send(ml ...*Msg) (rerr error) {
 			if reserr := c.sc.Reset(); reserr != nil {
 				rerr = errors.Join(rerr, reserr)
 			}
+			m.sendError = rse
+			rerr = errors.Join(rerr, m.sendError)
 			continue
 		}
 		w, err := c.sc.Data()
 		if err != nil {
-			rerr = errors.Join(rerr, fmt.Errorf("sending DATA command failed: %w", err))
+			m.sendError = &SendError{Reason: ErrSMTPData, errlist: []error{err}, isTemp: isTempError(err)}
+			rerr = errors.Join(rerr, m.sendError)
 			continue
 		}
 		_, err = m.WriteTo(w)
 		if err != nil {
-			rerr = errors.Join(rerr, fmt.Errorf("sending mail content failed: %w", err))
+			m.sendError = &SendError{Reason: ErrWriteContent, errlist: []error{err}, isTemp: isTempError(err)}
+			rerr = errors.Join(rerr, m.sendError)
 			continue
 		}
 
 		if err := w.Close(); err != nil {
-			rerr = errors.Join(rerr, fmt.Errorf("failed to close DATA writer: %w", err))
+			m.sendError = &SendError{Reason: ErrSMTPDataClose, errlist: []error{err}, isTemp: isTempError(err)}
+			rerr = errors.Join(rerr, m.sendError)
 			continue
 		}
 
 		if err := c.Reset(); err != nil {
-			rerr = errors.Join(rerr, fmt.Errorf("sending RSET command failed: %w", err))
+			m.sendError = &SendError{Reason: ErrSMTPReset, errlist: []error{err}, isTemp: isTempError(err)}
+			rerr = errors.Join(rerr, m.sendError)
 			continue
 		}
 		if err := c.checkConn(); err != nil {
-			rerr = errors.Join(rerr, fmt.Errorf("failed to check server connection: %w", err))
+			m.sendError = &SendError{Reason: ErrConnCheck, errlist: []error{err}, isTemp: isTempError(err)}
+			rerr = errors.Join(rerr, m.sendError)
 		}
 	}
 

client_test.go

@@ -7,6 +7,7 @@ package mail
 import (
 	"context"
 	"crypto/tls"
+	"errors"
 	"fmt"
 	"net/smtp"
 	"os"
@@ -989,6 +990,93 @@ func TestValidateLine(t *testing.T) {
 	}
 }
 
+// TestClient_Send_MsgSendError tests the Client.Send method with a broken recipient and verifies
+// that the SendError type works properly
+func TestClient_Send_MsgSendError(t *testing.T) {
+	if os.Getenv("TEST_ALLOW_SEND") == "" {
+		t.Skipf("TEST_ALLOW_SEND is not set. Skipping mail sending test")
+	}
+	var msgs []*Msg
+	rcpts := []string{"invalid@domain.tld", "invalid@address.invalid"}
+	for _, rcpt := range rcpts {
+		m := NewMsg()
+		_ = m.FromFormat("go-mail Test Mailer", os.Getenv("TEST_FROM"))
+		_ = m.To(rcpt)
+		m.Subject(fmt.Sprintf("This is a test mail from go-mail/v%s", VERSION))
+		m.SetBulk()
+		m.SetDate()
+		m.SetMessageID()
+		m.SetBodyString(TypeTextPlain, "This is a test mail from the go-mail library")
+		msgs = append(msgs, m)
+	}
+
+	c, err := getTestConnection(true)
+	if err != nil {
+		t.Skipf("failed to create test client: %s. Skipping tests", err)
+	}
+
+	ctx, cfn := context.WithTimeout(context.Background(), DefaultTimeout)
+	defer cfn()
+	if err := c.DialWithContext(ctx); err != nil {
+		t.Errorf("failed to dial to sending server: %s", err)
+	}
+	if err := c.Send(msgs...); err == nil {
+		t.Errorf("sending messages with broken recipients was supposed to fail but didn't")
+	}
+	if err := c.Close(); err != nil {
+		t.Errorf("failed to close client connection: %s", err)
+	}
+	for _, m := range msgs {
+		if !m.HasSendError() {
+			t.Errorf("message was expected to have a send error, but didn't")
+		}
+		se := &SendError{Reason: ErrSMTPRcptTo}
+		if !errors.Is(m.SendError(), se) {
+			t.Errorf("error mismatch, expected: %s, got: %s", se, m.SendError())
+		}
+		if m.SendErrorIsTemp() {
+			t.Errorf("message was not expected to be a temporary error, but reported as such")
+		}
+	}
+}
+
+// TestClient_DialAndSendWithContext_withSendError tests the Client.DialAndSendWithContext method
+// with a broken recipient to make sure that the returned error satisfies the Msg.SendError type
+func TestClient_DialAndSendWithContext_withSendError(t *testing.T) {
+	if os.Getenv("TEST_ALLOW_SEND") == "" {
+		t.Skipf("TEST_ALLOW_SEND is not set. Skipping mail sending test")
+	}
+	m := NewMsg()
+	_ = m.FromFormat("go-mail Test Mailer", os.Getenv("TEST_FROM"))
+	_ = m.To("invalid@domain.tld")
+	m.Subject(fmt.Sprintf("This is a test mail from go-mail/v%s", VERSION))
+	m.SetBulk()
+	m.SetDate()
+	m.SetMessageID()
+	m.SetBodyString(TypeTextPlain, "This is a test mail from the go-mail library")
+
+	c, err := getTestConnection(true)
+	if err != nil {
+		t.Skipf("failed to create test client: %s. Skipping tests", err)
+	}
+	ctx, cfn := context.WithTimeout(context.Background(), DefaultTimeout)
+	defer cfn()
+	err = c.DialAndSendWithContext(ctx, m)
+	if err == nil {
+		t.Errorf("expected DialAndSendWithContext with broken mail recipient to fail, but didn't")
+		return
+	}
+	var se *SendError
+	if !errors.As(err, &se) {
+		t.Errorf("expected *SendError type as returned error, but didn't")
+		return
+	}
+	if se.IsTemp() {
+		t.Errorf("expected permanent error but IsTemp() returned true")
+		return
+	}
+}
+
 // getTestConnection takes environment variables to establish a connection to a real
 // SMTP server to test all functionality that requires a connection
 func getTestConnection(auth bool) (*Client, error) {

doc.go

@@ -6,4 +6,4 @@
 package mail
 
 // VERSION is used in the default user agent string
-const VERSION = "0.3.6"
+const VERSION = "0.3.7"

msg.go

@@ -90,6 +90,9 @@ type Msg struct {
 
 	// middlewares is the list of middlewares to apply to the Msg before sending in FIFO order
 	middlewares []Middleware
+
+	// sendError holds the SendError in case a Msg could not be delivered during the Client.Send operation
+	sendError error
 }
 
 // SendmailPath is the default system path to the sendmail binary
@@ -957,6 +960,27 @@ func (m *Msg) UpdateReader(r *Reader) {
 	r.err = err
 }
 
+// HasSendError returns true if the Msg experienced an error during the message delivery and the
+// sendError field of the Msg is not nil
+func (m *Msg) HasSendError() bool {
+	return m.sendError != nil
+}
+
+// SendErrorIsTemp returns true if the Msg experienced an error during the message delivery and the
+// corresponding error was of temporary nature and should be retried later
+func (m *Msg) SendErrorIsTemp() bool {
+	var e *SendError
+	if errors.As(m.sendError, &e) {
+		return e.isTemp
+	}
+	return false
+}
+
+// SendError returns the sendError field of the Msg
+func (m *Msg) SendError() error {
+	return m.sendError
+}
+
 // encodeString encodes a string based on the configured message encoder and the corresponding
 // charset for the Msg
 func (m *Msg) encodeString(s string) string {

senderror.go

@@ -0,0 +1,145 @@
+// SPDX-FileCopyrightText: 2022 Winni Neessen <winni@neessen.dev>
+//
+// SPDX-License-Identifier: MIT
+
+package mail
+
+import (
+	"errors"
+	"strings"
+)
+
+// List of SendError reasons
+const (
+	// ErrGetSender is returned if the Msg.GetSender method fails during a Client.Send
+	ErrGetSender SendErrReason = iota
+
+	// ErrGetRcpts is returned if the Msg.GetRecipients method fails during a Client.Send
+	ErrGetRcpts
+
+	// ErrSMTPMailFrom is returned if the Msg delivery failed when sending the MAIL FROM command
+	// to the sending SMTP server
+	ErrSMTPMailFrom
+
+	// ErrSMTPRcptTo is returned if the Msg delivery failed when sending the RCPT TO command
+	// to the sending SMTP server
+	ErrSMTPRcptTo
+
+	// ErrSMTPData is returned if the Msg delivery failed when sending the DATA command
+	// to the sending SMTP server
+	ErrSMTPData
+
+	// ErrSMTPDataClose is returned if the Msg delivery failed when trying to close the
+	// Client data writer
+	ErrSMTPDataClose
+
+	// ErrSMTPReset is returned if the Msg delivery failed when sending the RSET command
+	// to the sending SMTP server
+	ErrSMTPReset
+
+	// ErrWriteContent is returned if the Msg delivery failed when sending Msg content
+	// to the Client writer
+	ErrWriteContent
+
+	// ErrConnCheck is returned if the Msg delivery failed when checking if the SMTP
+	// server connection is still working
+	ErrConnCheck
+
+	// ErrNoUnencoded is returned if the Msg delivery failed when the Msg is configured for
+	// unencoded delivery but the server does not support this
+	ErrNoUnencoded
+
+	// ErrAmbiguous is a generalized delivery error for the SendError type that is
+	// returned if the exact reason for the delivery failure is ambiguous
+	ErrAmbiguous
+)
+
+// SendError is an error wrapper for delivery errors of the Msg
+type SendError struct {
+	Reason  SendErrReason
+	isTemp  bool
+	errlist []error
+	rcpt    []string
+}
+
+// SendErrReason represents a comparable reason on why the delivery failed
+type SendErrReason int
+
+// Error implements the error interface for the SendError type
+func (e *SendError) Error() string {
+	if e.Reason > 10 {
+		return "unknown reason"
+	}
+
+	var em strings.Builder
+	em.WriteString(e.Reason.String())
+	if len(e.errlist) > 0 {
+		em.WriteRune(':')
+		for i := range e.errlist {
+			em.WriteRune(' ')
+			em.WriteString(e.errlist[i].Error())
+			if i != len(e.errlist)-1 {
+				em.WriteString(", ")
+			}
+		}
+	}
+	if len(e.rcpt) > 0 {
+		em.WriteString(", affected recipient(s): ")
+		for i := range e.rcpt {
+			em.WriteString(e.rcpt[i])
+			if i != len(e.rcpt)-1 {
+				em.WriteString(", ")
+			}
+		}
+	}
+	return em.String()
+}
+
+// Is implements the errors.Is functionality and compares the SendErrReason
+func (e *SendError) Is(et error) bool {
+	var t *SendError
+	if errors.As(et, &t) {
+		return e.Reason == t.Reason && e.isTemp == t.isTemp
+	}
+	return false
+}
+
+// IsTemp returns true if the delivery error is of temporary nature and can be retried
+func (e *SendError) IsTemp() bool {
+	return e.isTemp
+}
+
+// String implements the Stringer interface for the SendErrReason
+func (r SendErrReason) String() string {
+	switch r {
+	case ErrGetSender:
+		return "getting sender address"
+	case ErrGetRcpts:
+		return "getting recipient addresses"
+	case ErrSMTPMailFrom:
+		return "sending SMTP MAIL FROM command"
+	case ErrSMTPRcptTo:
+		return "sending SMTP RCPT TO command"
+	case ErrSMTPData:
+		return "sending SMTP DATA command"
+	case ErrSMTPDataClose:
+		return "closing SMTP DATA writer"
+	case ErrSMTPReset:
+		return "sending SMTP RESET command"
+	case ErrWriteContent:
+		return "sending message content"
+	case ErrConnCheck:
+		return "checking SMTP connection"
+	case ErrNoUnencoded:
+		return ErrServerNoUnencoded.Error()
+	case ErrAmbiguous:
+		return "ambiguous reason, check Msg.SendError for message specific reasons"
+	}
+	return "unknown reason"
+}
+
+// isTempError checks the given SMTP error and returns true if the given error is of temporary nature
+// and should be retried
+func isTempError(e error) bool {
+	return e.Error()[0] == '4'
+}

senderror_test.go

@@ -0,0 +1,89 @@
+// SPDX-FileCopyrightText: 2022 Winni Neessen <winni@neessen.dev>
+//
+// SPDX-License-Identifier: MIT
+
+package mail
+
+import (
+	"errors"
+	"fmt"
+	"strings"
+	"testing"
+)
+
+// TestSendError_Error tests the SendError and SendErrReason error handling methods
+func TestSendError_Error(t *testing.T) {
+	tl := []struct {
+		n  string
+		r  SendErrReason
+		te bool
+	}{
+		{"ErrGetSender/temp", ErrGetSender, true},
+		{"ErrGetSender/perm", ErrGetSender, false},
+		{"ErrGetRcpts/temp", ErrGetRcpts, true},
+		{"ErrGetRcpts/perm", ErrGetRcpts, false},
+		{"ErrSMTPMailFrom/temp", ErrSMTPMailFrom, true},
+		{"ErrSMTPMailFrom/perm", ErrSMTPMailFrom, false},
+		{"ErrSMTPRcptTo/temp", ErrSMTPRcptTo, true},
+		{"ErrSMTPRcptTo/perm", ErrSMTPRcptTo, false},
+		{"ErrSMTPData/temp", ErrSMTPData, true},
+		{"ErrSMTPData/perm", ErrSMTPData, false},
+		{"ErrSMTPDataClose/temp", ErrSMTPDataClose, true},
+		{"ErrSMTPDataClose/perm", ErrSMTPDataClose, false},
+		{"ErrSMTPReset/temp", ErrSMTPReset, true},
+		{"ErrSMTPReset/perm", ErrSMTPReset, false},
+		{"ErrWriteContent/temp", ErrWriteContent, true},
+		{"ErrWriteContent/perm", ErrWriteContent, false},
+		{"ErrConnCheck/temp", ErrConnCheck, true},
+		{"ErrConnCheck/perm", ErrConnCheck, false},
+		{"ErrNoUnencoded/temp", ErrNoUnencoded, true},
+		{"ErrNoUnencoded/perm", ErrNoUnencoded, false},
+		{"ErrAmbiguous/temp", ErrAmbiguous, true},
+		{"ErrAmbiguous/perm", ErrAmbiguous, false},
+		{"Unknown/temp", 9999, true},
+		{"Unknown/perm", 9999, false},
+	}
+
+	for _, tt := range tl {
+		t.Run(tt.n, func(t *testing.T) {
+			if err := returnSendError(tt.r, tt.te); err != nil {
+				exp := &SendError{Reason: tt.r, isTemp: tt.te}
+				if !errors.Is(err, exp) {
+					t.Errorf("error mismatch, expected: %s (temp: %t), got: %s (temp: %t)", tt.r, tt.te,
+						exp.Error(), exp.isTemp)
+				}
+				if !strings.Contains(fmt.Sprintf("%s", err), tt.r.String()) {
+					t.Errorf("error string mismatch, expected: %s, got: %s",
+						tt.r.String(), fmt.Sprintf("%s", err))
+				}
+			}
+		})
+	}
+}
+
+func TestSendError_IsTemp(t *testing.T) {
+	var se *SendError
+	err1 := returnSendError(ErrAmbiguous, true)
+	if !errors.As(err1, &se) {
+		t.Errorf("error mismatch, expected error to be of type *SendError")
+		return
+	}
+	if errors.As(err1, &se) && !se.IsTemp() {
+		t.Errorf("error mismatch, expected temporary error")
+		return
+	}
+	err2 := returnSendError(ErrAmbiguous, false)
+	if !errors.As(err2, &se) {
+		t.Errorf("error mismatch, expected error to be of type *SendError")
+		return
+	}
+	if errors.As(err2, &se) && se.IsTemp() {
+		t.Errorf("error mismatch, expected non-temporary error")
+		return
+	}
+}
+
+// returnSendError is a helper method to retunr a SendError with a specific reason
+func returnSendError(r SendErrReason, t bool) error {
+	return &SendError{Reason: r, isTemp: t}
+}