Merge 4b60557518 into 077c85bea0

Bump sonarsource/sonarqube-scan-action from f885e52a7572cf7943f28637e75730227df2dbf2 to 884b79409bbd464b2a59edc326a4b77dc56b2195

.github/workflows/codecov.yml

@@ -36,10 +36,10 @@ jobs:
     strategy:
       matrix:
         os: [ubuntu-latest, macos-latest, windows-latest]
-        go: ['1.20', '1.21', '1.22', '1.23']
+        go: ['1.19', '1.20', '1.23']
     steps:
     - name: Harden Runner
-      uses: step-security/harden-runner@5c7944e73c4c2a096b17a9cb74d65b6c2bbafbde # v2.9.1
+      uses: step-security/harden-runner@91182cccc01eb5e619899d80e4e971d6181294a7 # v2.10.1
       with:
         egress-policy: audit
 

.github/workflows/codeql-analysis.yml

@@ -45,7 +45,7 @@ jobs:
 
     steps:
     - name: Harden Runner
-      uses: step-security/harden-runner@5c7944e73c4c2a096b17a9cb74d65b6c2bbafbde # v2.9.1
+      uses: step-security/harden-runner@91182cccc01eb5e619899d80e4e971d6181294a7 # v2.10.1
       with:
         egress-policy: audit
 
@@ -54,7 +54,7 @@ jobs:
 
     # Initializes the CodeQL tools for scanning.
     - name: Initialize CodeQL
-      uses: github/codeql-action/init@4dd16135b69a43b6c8efb853346f8437d92d3c93 # v3.26.6
+      uses: github/codeql-action/init@461ef6c76dfe95d5c364de2f431ddbd31a417628 # v3.26.9
       with:
         languages: ${{ matrix.language }}
         # If you wish to specify custom queries, you can do so here or in a config file.
@@ -65,7 +65,7 @@ jobs:
     # Autobuild attempts to build any compiled languages  (C/C++, C#, or Java).
     # If this step fails, then you should remove it and run the build manually (see below)
     - name: Autobuild
-      uses: github/codeql-action/autobuild@4dd16135b69a43b6c8efb853346f8437d92d3c93 # v3.26.6
+      uses: github/codeql-action/autobuild@461ef6c76dfe95d5c364de2f431ddbd31a417628 # v3.26.9
 
     # ℹ️ Command-line programs to run using the OS shell.
     # 📚 https://git.io/JvXDl
@@ -79,4 +79,4 @@ jobs:
     #   make release
 
     - name: Perform CodeQL Analysis
-      uses: github/codeql-action/analyze@4dd16135b69a43b6c8efb853346f8437d92d3c93 # v3.26.6
+      uses: github/codeql-action/analyze@461ef6c76dfe95d5c364de2f431ddbd31a417628 # v3.26.9

.github/workflows/dependency-review.yml

@@ -21,7 +21,7 @@ jobs:
     runs-on: ubuntu-latest
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@5c7944e73c4c2a096b17a9cb74d65b6c2bbafbde # v2.9.1
+        uses: step-security/harden-runner@91182cccc01eb5e619899d80e4e971d6181294a7 # v2.10.1
         with:
           egress-policy: audit
 

.github/workflows/golangci-lint.yml

@@ -20,7 +20,7 @@ jobs:
     runs-on: ubuntu-latest
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@5c7944e73c4c2a096b17a9cb74d65b6c2bbafbde # v2.9.1
+        uses: step-security/harden-runner@91182cccc01eb5e619899d80e4e971d6181294a7 # v2.10.1
         with:
           egress-policy: audit
 

.github/workflows/govulncheck.yml

@@ -14,7 +14,7 @@ jobs:
     runs-on: ubuntu-latest
     steps: 
     - name: Harden Runner
-      uses: step-security/harden-runner@5c7944e73c4c2a096b17a9cb74d65b6c2bbafbde # v2.9.1
+      uses: step-security/harden-runner@91182cccc01eb5e619899d80e4e971d6181294a7 # v2.10.1
       with:
         egress-policy: audit
     - name: Run govulncheck

.github/workflows/reuse.yml

@@ -14,7 +14,7 @@ jobs:
     runs-on: ubuntu-latest
     steps: 
     - name: Harden Runner
-      uses: step-security/harden-runner@5c7944e73c4c2a096b17a9cb74d65b6c2bbafbde # v2.9.1
+      uses: step-security/harden-runner@91182cccc01eb5e619899d80e4e971d6181294a7 # v2.10.1
       with:
         egress-policy: audit
 

.github/workflows/scorecards.yml

@@ -35,7 +35,7 @@ jobs:
 
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@5c7944e73c4c2a096b17a9cb74d65b6c2bbafbde # v2.9.1
+        uses: step-security/harden-runner@91182cccc01eb5e619899d80e4e971d6181294a7 # v2.10.1
         with:
           egress-policy: audit
 
@@ -75,6 +75,6 @@ jobs:
 
       # Upload the results to GitHub's code scanning dashboard.
       - name: "Upload to code-scanning"
-        uses: github/codeql-action/upload-sarif@4dd16135b69a43b6c8efb853346f8437d92d3c93 # v3.26.6
+        uses: github/codeql-action/upload-sarif@461ef6c76dfe95d5c364de2f431ddbd31a417628 # v3.26.9
         with:
           sarif_file: results.sarif

.github/workflows/sonarqube.yml

@@ -27,7 +27,7 @@ jobs:
     runs-on: ubuntu-latest
     steps:
       - name: Harden Runner
-        uses: step-security/harden-runner@5c7944e73c4c2a096b17a9cb74d65b6c2bbafbde # v2.9.1
+        uses: step-security/harden-runner@91182cccc01eb5e619899d80e4e971d6181294a7 # v2.10.1
         with:
           egress-policy: audit
 
@@ -44,7 +44,7 @@ jobs:
         run: |
           go test -v -race --coverprofile=./cov.out ./...
 
-      - uses: sonarsource/sonarqube-scan-action@0c0f3958d90fc466625f1d1af1f47bddd4cc6bd1 # master
+      - uses: sonarsource/sonarqube-scan-action@884b79409bbd464b2a59edc326a4b77dc56b2195 # master
         env:
           SONAR_TOKEN: ${{ secrets.SONAR_TOKEN }}
           SONAR_HOST_URL: ${{ secrets.SONAR_HOST_URL }}

client.go

@@ -787,3 +787,100 @@ func (c *Client) auth() error {
 	}
 	return nil
 }
+
+// sendSingleMsg sends out a single message and returns an error if the transmission/delivery fails.
+// It is invoked by the public Send methods
+func (c *Client) sendSingleMsg(message *Msg) error {
+	if message.encoding == NoEncoding {
+		if ok, _ := c.smtpClient.Extension("8BITMIME"); !ok {
+			return &SendError{Reason: ErrNoUnencoded, isTemp: false, affectedMsg: message}
+		}
+	}
+	from, err := message.GetSender(false)
+	if err != nil {
+		return &SendError{
+			Reason: ErrGetSender, errlist: []error{err}, isTemp: isTempError(err),
+			affectedMsg: message,
+		}
+	}
+	rcpts, err := message.GetRecipients()
+	if err != nil {
+		return &SendError{
+			Reason: ErrGetRcpts, errlist: []error{err}, isTemp: isTempError(err),
+			affectedMsg: message,
+		}
+	}
+
+	if c.dsn {
+		if c.dsnmrtype != "" {
+			c.smtpClient.SetDSNMailReturnOption(string(c.dsnmrtype))
+		}
+	}
+	if err = c.smtpClient.Mail(from); err != nil {
+		retError := &SendError{
+			Reason: ErrSMTPMailFrom, errlist: []error{err}, isTemp: isTempError(err),
+			affectedMsg: message,
+		}
+		if resetSendErr := c.smtpClient.Reset(); resetSendErr != nil {
+			retError.errlist = append(retError.errlist, resetSendErr)
+		}
+		return retError
+	}
+	hasError := false
+	rcptSendErr := &SendError{affectedMsg: message}
+	rcptSendErr.errlist = make([]error, 0)
+	rcptSendErr.rcpt = make([]string, 0)
+	rcptNotifyOpt := strings.Join(c.dsnrntype, ",")
+	c.smtpClient.SetDSNRcptNotifyOption(rcptNotifyOpt)
+	for _, rcpt := range rcpts {
+		if err = c.smtpClient.Rcpt(rcpt); err != nil {
+			rcptSendErr.Reason = ErrSMTPRcptTo
+			rcptSendErr.errlist = append(rcptSendErr.errlist, err)
+			rcptSendErr.rcpt = append(rcptSendErr.rcpt, rcpt)
+			rcptSendErr.isTemp = isTempError(err)
+			hasError = true
+		}
+	}
+	if hasError {
+		if resetSendErr := c.smtpClient.Reset(); resetSendErr != nil {
+			rcptSendErr.errlist = append(rcptSendErr.errlist, resetSendErr)
+		}
+		return rcptSendErr
+	}
+	writer, err := c.smtpClient.Data()
+	if err != nil {
+		return &SendError{
+			Reason: ErrSMTPData, errlist: []error{err}, isTemp: isTempError(err),
+			affectedMsg: message,
+		}
+	}
+	_, err = message.WriteTo(writer)
+	if err != nil {
+		return &SendError{
+			Reason: ErrWriteContent, errlist: []error{err}, isTemp: isTempError(err),
+			affectedMsg: message,
+		}
+	}
+	message.isDelivered = true
+
+	if err = writer.Close(); err != nil {
+		return &SendError{
+			Reason: ErrSMTPDataClose, errlist: []error{err}, isTemp: isTempError(err),
+			affectedMsg: message,
+		}
+	}
+
+	if err = c.Reset(); err != nil {
+		return &SendError{
+			Reason: ErrSMTPReset, errlist: []error{err}, isTemp: isTempError(err),
+			affectedMsg: message,
+		}
+	}
+	if err = c.checkConn(); err != nil {
+		return &SendError{
+			Reason: ErrConnCheck, errlist: []error{err}, isTemp: isTempError(err),
+			affectedMsg: message,
+		}
+	}
+	return nil
+}

client_119.go

@@ -7,111 +7,23 @@
 
 package mail
 
-import "strings"
+import "errors"
 
 // Send sends out the mail message
 func (c *Client) Send(messages ...*Msg) error {
-	if cerr := c.checkConn(); cerr != nil {
-		return &SendError{Reason: ErrConnCheck, errlist: []error{cerr}, isTemp: isTempError(cerr)}
+	if err := c.checkConn(); err != nil {
+		return &SendError{Reason: ErrConnCheck, errlist: []error{err}, isTemp: isTempError(err)}
 	}
 	var errs []*SendError
-	for _, message := range messages {
-		message.sendError = nil
-		if message.encoding == NoEncoding {
-			if ok, _ := c.smtpClient.Extension("8BITMIME"); !ok {
-				sendErr := &SendError{Reason: ErrNoUnencoded, isTemp: false}
-				message.sendError = sendErr
-				errs = append(errs, sendErr)
-				continue
-			}
-		}
-		from, err := message.GetSender(false)
-		if err != nil {
-			sendErr := &SendError{Reason: ErrGetSender, errlist: []error{err}, isTemp: isTempError(err)}
-			message.sendError = sendErr
-			errs = append(errs, sendErr)
-			continue
-		}
-		rcpts, err := message.GetRecipients()
-		if err != nil {
-			sendErr := &SendError{Reason: ErrGetRcpts, errlist: []error{err}, isTemp: isTempError(err)}
-			message.sendError = sendErr
-			errs = append(errs, sendErr)
-			continue
-		}
+	for id, message := range messages {
+		if sendErr := c.sendSingleMsg(message); sendErr != nil {
+			messages[id].sendError = sendErr
 
-		if c.dsn {
-			if c.dsnmrtype != "" {
-				c.smtpClient.SetDSNMailReturnOption(string(c.dsnmrtype))
+			var msgSendErr *SendError
+			if errors.As(sendErr, &msgSendErr) {
+				errs = append(errs, msgSendErr)
 			}
 		}
-		if err = c.smtpClient.Mail(from); err != nil {
-			sendErr := &SendError{Reason: ErrSMTPMailFrom, errlist: []error{err}, isTemp: isTempError(err)}
-			if resetSendErr := c.smtpClient.Reset(); resetSendErr != nil {
-				sendErr.errlist = append(sendErr.errlist, resetSendErr)
-			}
-			message.sendError = sendErr
-			errs = append(errs, sendErr)
-			continue
-		}
-		failed := false
-		rcptSendErr := &SendError{}
-		rcptSendErr.errlist = make([]error, 0)
-		rcptSendErr.rcpt = make([]string, 0)
-		rcptNotifyOpt := strings.Join(c.dsnrntype, ",")
-		c.smtpClient.SetDSNRcptNotifyOption(rcptNotifyOpt)
-		for _, rcpt := range rcpts {
-			if err = c.smtpClient.Rcpt(rcpt); err != nil {
-				rcptSendErr.Reason = ErrSMTPRcptTo
-				rcptSendErr.errlist = append(rcptSendErr.errlist, err)
-				rcptSendErr.rcpt = append(rcptSendErr.rcpt, rcpt)
-				rcptSendErr.isTemp = isTempError(err)
-				failed = true
-			}
-		}
-		if failed {
-			if resetSendErr := c.smtpClient.Reset(); resetSendErr != nil {
-				rcptSendErr.errlist = append(rcptSendErr.errlist, err)
-			}
-			message.sendError = rcptSendErr
-			errs = append(errs, rcptSendErr)
-			continue
-		}
-		writer, err := c.smtpClient.Data()
-		if err != nil {
-			sendErr := &SendError{Reason: ErrSMTPData, errlist: []error{err}, isTemp: isTempError(err)}
-			message.sendError = sendErr
-			errs = append(errs, sendErr)
-			continue
-		}
-		_, err = message.WriteTo(writer)
-		if err != nil {
-			sendErr := &SendError{Reason: ErrWriteContent, errlist: []error{err}, isTemp: isTempError(err)}
-			message.sendError = sendErr
-			errs = append(errs, sendErr)
-			continue
-		}
-		message.isDelivered = true
-
-		if err = writer.Close(); err != nil {
-			sendErr := &SendError{Reason: ErrSMTPDataClose, errlist: []error{err}, isTemp: isTempError(err)}
-			message.sendError = sendErr
-			errs = append(errs, sendErr)
-			continue
-		}
-
-		if err = c.Reset(); err != nil {
-			sendErr := &SendError{Reason: ErrSMTPReset, errlist: []error{err}, isTemp: isTempError(err)}
-			message.sendError = sendErr
-			errs = append(errs, sendErr)
-			continue
-		}
-		if err = c.checkConn(); err != nil {
-			sendErr := &SendError{Reason: ErrConnCheck, errlist: []error{err}, isTemp: isTempError(err)}
-			message.sendError = sendErr
-			errs = append(errs, sendErr)
-			continue
-		}
 	}
 
 	if len(errs) > 0 {

client_120.go

@@ -9,7 +9,6 @@ package mail
 
 import (
 	"errors"
-	"strings"
 )
 
 // Send sends out the mail message
@@ -18,92 +17,16 @@ func (c *Client) Send(messages ...*Msg) (returnErr error) {
 		returnErr = &SendError{Reason: ErrConnCheck, errlist: []error{err}, isTemp: isTempError(err)}
 		return
 	}
-	for _, message := range messages {
-		message.sendError = nil
-		if message.encoding == NoEncoding {
-			if ok, _ := c.smtpClient.Extension("8BITMIME"); !ok {
-				message.sendError = &SendError{Reason: ErrNoUnencoded, isTemp: false}
-				returnErr = errors.Join(returnErr, message.sendError)
-				continue
-			}
-		}
-		from, err := message.GetSender(false)
-		if err != nil {
-			message.sendError = &SendError{Reason: ErrGetSender, errlist: []error{err}, isTemp: isTempError(err)}
-			returnErr = errors.Join(returnErr, message.sendError)
-			continue
-		}
-		rcpts, err := message.GetRecipients()
-		if err != nil {
-			message.sendError = &SendError{Reason: ErrGetRcpts, errlist: []error{err}, isTemp: isTempError(err)}
-			returnErr = errors.Join(returnErr, message.sendError)
-			continue
-		}
 
-		if c.dsn {
-			if c.dsnmrtype != "" {
-				c.smtpClient.SetDSNMailReturnOption(string(c.dsnmrtype))
-			}
-		}
-		if err = c.smtpClient.Mail(from); err != nil {
-			message.sendError = &SendError{Reason: ErrSMTPMailFrom, errlist: []error{err}, isTemp: isTempError(err)}
-			returnErr = errors.Join(returnErr, message.sendError)
-			if resetSendErr := c.smtpClient.Reset(); resetSendErr != nil {
-				returnErr = errors.Join(returnErr, resetSendErr)
-			}
-			continue
-		}
-		failed := false
-		rcptSendErr := &SendError{}
-		rcptSendErr.errlist = make([]error, 0)
-		rcptSendErr.rcpt = make([]string, 0)
-		rcptNotifyOpt := strings.Join(c.dsnrntype, ",")
-		c.smtpClient.SetDSNRcptNotifyOption(rcptNotifyOpt)
-		for _, rcpt := range rcpts {
-			if err = c.smtpClient.Rcpt(rcpt); err != nil {
-				rcptSendErr.Reason = ErrSMTPRcptTo
-				rcptSendErr.errlist = append(rcptSendErr.errlist, err)
-				rcptSendErr.rcpt = append(rcptSendErr.rcpt, rcpt)
-				rcptSendErr.isTemp = isTempError(err)
-				failed = true
-			}
-		}
-		if failed {
-			if resetSendErr := c.smtpClient.Reset(); resetSendErr != nil {
-				returnErr = errors.Join(returnErr, resetSendErr)
-			}
-			message.sendError = rcptSendErr
-			returnErr = errors.Join(returnErr, message.sendError)
-			continue
-		}
-		writer, err := c.smtpClient.Data()
-		if err != nil {
-			message.sendError = &SendError{Reason: ErrSMTPData, errlist: []error{err}, isTemp: isTempError(err)}
-			returnErr = errors.Join(returnErr, message.sendError)
-			continue
-		}
-		_, err = message.WriteTo(writer)
-		if err != nil {
-			message.sendError = &SendError{Reason: ErrWriteContent, errlist: []error{err}, isTemp: isTempError(err)}
-			returnErr = errors.Join(returnErr, message.sendError)
-			continue
-		}
-		message.isDelivered = true
+	var errs []error
+	defer func() {
+		returnErr = errors.Join(errs...)
+	}()
 
-		if err = writer.Close(); err != nil {
-			message.sendError = &SendError{Reason: ErrSMTPDataClose, errlist: []error{err}, isTemp: isTempError(err)}
-			returnErr = errors.Join(returnErr, message.sendError)
-			continue
-		}
-
-		if err = c.Reset(); err != nil {
-			message.sendError = &SendError{Reason: ErrSMTPReset, errlist: []error{err}, isTemp: isTempError(err)}
-			returnErr = errors.Join(returnErr, message.sendError)
-			continue
-		}
-		if err = c.checkConn(); err != nil {
-			message.sendError = &SendError{Reason: ErrConnCheck, errlist: []error{err}, isTemp: isTempError(err)}
-			returnErr = errors.Join(returnErr, message.sendError)
+	for id, message := range messages {
+		if sendErr := c.sendSingleMsg(message); sendErr != nil {
+			messages[id].sendError = sendErr
+			errs = append(errs, sendErr)
 		}
 	}
 

client_test.go

@@ -5,6 +5,7 @@
 package mail
 
 import (
+	"bufio"
 	"context"
 	"crypto/tls"
 	"errors"
@@ -21,11 +22,18 @@ import (
 	"github.com/wneessen/go-mail/smtp"
 )
 
+const (
 	// DefaultHost is used as default hostname for the Client
-const DefaultHost = "localhost"
-
-// TestRcpt
-const TestRcpt = "go-mail@mytrashmailer.com"
+	DefaultHost = "localhost"
+	// TestRcpt is a trash mail address to send test mails to
+	TestRcpt = "go-mail@mytrashmailer.com"
+	// TestServerProto is the protocol used for the simple SMTP test server
+	TestServerProto = "tcp"
+	// 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
+)
 
 // TestNewClient tests the NewClient() method with its default options
 func TestNewClient(t *testing.T) {
@@ -629,7 +637,7 @@ func TestClient_DialWithContext(t *testing.T) {
 // TestClient_DialWithContext_Fallback tests the Client.DialWithContext method with the fallback
 // port functionality
 func TestClient_DialWithContext_Fallback(t *testing.T) {
-	c, err := getTestConnection(true)
+	c, err := getTestConnectionNoTestPort(true)
 	if err != nil {
 		t.Skipf("failed to create test client: %s. Skipping tests", err)
 	}
@@ -1251,6 +1259,475 @@ func TestClient_DialAndSendWithContext_withSendError(t *testing.T) {
 	}
 }
 
+func TestClient_SendErrorNoEncoding(t *testing.T) {
+	ctx, cancel := context.WithCancel(context.Background())
+	defer cancel()
+
+	featureSet := "250-AUTH PLAIN\r\n250-DSN\r\n250 SMTPUTF8"
+	serverPort := TestServerPortBase + 1
+	go func() {
+		if err := simpleSMTPServer(ctx, featureSet, false, serverPort); err != nil {
+			t.Errorf("failed to start test server: %s", err)
+			return
+		}
+	}()
+	time.Sleep(time.Millisecond * 300)
+
+	message := NewMsg()
+	if err := message.From("valid-from@domain.tld"); err != nil {
+		t.Errorf("failed to set FROM address: %s", err)
+		return
+	}
+	if err := message.To("valid-to@domain.tld"); err != nil {
+		t.Errorf("failed to set TO address: %s", err)
+		return
+	}
+	message.Subject("Test subject")
+	message.SetBodyString(TypeTextPlain, "Test body")
+	message.SetMessageIDWithValue("this.is.a.message.id")
+	message.SetEncoding(NoEncoding)
+
+	client, err := NewClient(TestServerAddr, WithPort(serverPort),
+		WithTLSPortPolicy(NoTLS), WithSMTPAuth(SMTPAuthPlain),
+		WithUsername("toni@tester.com"),
+		WithPassword("V3ryS3cr3t+"))
+	if err != nil {
+		t.Errorf("unable to create new client: %s", err)
+	}
+	if err = client.DialWithContext(context.Background()); err != nil {
+		t.Errorf("failed to dial to test server: %s", err)
+	}
+	if err = client.Send(message); err == nil {
+		t.Error("expected Send() to fail but didn't")
+	}
+
+	var sendErr *SendError
+	if !errors.As(err, &sendErr) {
+		t.Errorf("expected *SendError type as returned error, but got %T", sendErr)
+	}
+	if errors.As(err, &sendErr) {
+		if sendErr.IsTemp() {
+			t.Errorf("expected permanent error but IsTemp() returned true")
+		}
+		if sendErr.Reason != ErrNoUnencoded {
+			t.Errorf("expected ErrNoUnencoded error, but got %s", sendErr.Reason)
+		}
+		if !strings.EqualFold(sendErr.MessageID(), "<this.is.a.message.id>") {
+			t.Errorf("expected message ID: %q, but got %q", "<this.is.a.message.id>",
+				sendErr.MessageID())
+		}
+		if sendErr.Msg() == nil {
+			t.Errorf("expected message to be set, but got nil")
+		}
+	}
+
+	if err = client.Close(); err != nil {
+		t.Errorf("failed to close server connection: %s", err)
+	}
+}
+
+func TestClient_SendErrorMailFrom(t *testing.T) {
+	ctx, cancel := context.WithCancel(context.Background())
+	defer cancel()
+
+	serverPort := TestServerPortBase + 2
+	featureSet := "250-AUTH PLAIN\r\n250-8BITMIME\r\n250-DSN\r\n250 SMTPUTF8"
+	go func() {
+		if err := simpleSMTPServer(ctx, featureSet, false, serverPort); err != nil {
+			t.Errorf("failed to start test server: %s", err)
+			return
+		}
+	}()
+	time.Sleep(time.Millisecond * 300)
+
+	message := NewMsg()
+	if err := message.From("invalid-from@domain.tld"); err != nil {
+		t.Errorf("failed to set FROM address: %s", err)
+		return
+	}
+	if err := message.To("valid-to@domain.tld"); err != nil {
+		t.Errorf("failed to set TO address: %s", err)
+		return
+	}
+	message.Subject("Test subject")
+	message.SetBodyString(TypeTextPlain, "Test body")
+	message.SetMessageIDWithValue("this.is.a.message.id")
+
+	client, err := NewClient(TestServerAddr, WithPort(serverPort),
+		WithTLSPortPolicy(NoTLS), WithSMTPAuth(SMTPAuthPlain),
+		WithUsername("toni@tester.com"),
+		WithPassword("V3ryS3cr3t+"))
+	if err != nil {
+		t.Errorf("unable to create new client: %s", err)
+	}
+	if err = client.DialWithContext(context.Background()); err != nil {
+		t.Errorf("failed to dial to test server: %s", err)
+	}
+	if err = client.Send(message); err == nil {
+		t.Error("expected Send() to fail but didn't")
+	}
+
+	var sendErr *SendError
+	if !errors.As(err, &sendErr) {
+		t.Errorf("expected *SendError type as returned error, but got %T", sendErr)
+	}
+	if errors.As(err, &sendErr) {
+		if sendErr.IsTemp() {
+			t.Errorf("expected permanent error but IsTemp() returned true")
+		}
+		if sendErr.Reason != ErrSMTPMailFrom {
+			t.Errorf("expected ErrSMTPMailFrom error, but got %s", sendErr.Reason)
+		}
+		if !strings.EqualFold(sendErr.MessageID(), "<this.is.a.message.id>") {
+			t.Errorf("expected message ID: %q, but got %q", "<this.is.a.message.id>",
+				sendErr.MessageID())
+		}
+		if sendErr.Msg() == nil {
+			t.Errorf("expected message to be set, but got nil")
+		}
+	}
+
+	if err = client.Close(); err != nil {
+		t.Errorf("failed to close server connection: %s", err)
+	}
+}
+
+func TestClient_SendErrorMailFromReset(t *testing.T) {
+	ctx, cancel := context.WithCancel(context.Background())
+	defer cancel()
+
+	serverPort := TestServerPortBase + 3
+	featureSet := "250-AUTH PLAIN\r\n250-8BITMIME\r\n250-DSN\r\n250 SMTPUTF8"
+	go func() {
+		if err := simpleSMTPServer(ctx, featureSet, true, serverPort); err != nil {
+			t.Errorf("failed to start test server: %s", err)
+			return
+		}
+	}()
+	time.Sleep(time.Millisecond * 300)
+
+	message := NewMsg()
+	if err := message.From("invalid-from@domain.tld"); err != nil {
+		t.Errorf("failed to set FROM address: %s", err)
+		return
+	}
+	if err := message.To("valid-to@domain.tld"); err != nil {
+		t.Errorf("failed to set TO address: %s", err)
+		return
+	}
+	message.Subject("Test subject")
+	message.SetBodyString(TypeTextPlain, "Test body")
+	message.SetMessageIDWithValue("this.is.a.message.id")
+
+	client, err := NewClient(TestServerAddr, WithPort(serverPort),
+		WithTLSPortPolicy(NoTLS), WithSMTPAuth(SMTPAuthPlain),
+		WithUsername("toni@tester.com"),
+		WithPassword("V3ryS3cr3t+"))
+	if err != nil {
+		t.Errorf("unable to create new client: %s", err)
+	}
+	if err = client.DialWithContext(context.Background()); err != nil {
+		t.Errorf("failed to dial to test server: %s", err)
+	}
+	if err = client.Send(message); err == nil {
+		t.Error("expected Send() to fail but didn't")
+	}
+
+	var sendErr *SendError
+	if !errors.As(err, &sendErr) {
+		t.Errorf("expected *SendError type as returned error, but got %T", sendErr)
+	}
+	if errors.As(err, &sendErr) {
+		if sendErr.IsTemp() {
+			t.Errorf("expected permanent error but IsTemp() returned true")
+		}
+		if sendErr.Reason != ErrSMTPMailFrom {
+			t.Errorf("expected ErrSMTPMailFrom error, but got %s", sendErr.Reason)
+		}
+		if !strings.EqualFold(sendErr.MessageID(), "<this.is.a.message.id>") {
+			t.Errorf("expected message ID: %q, but got %q", "<this.is.a.message.id>",
+				sendErr.MessageID())
+		}
+		if len(sendErr.errlist) != 2 {
+			t.Errorf("expected 2 errors, but got %d", len(sendErr.errlist))
+			return
+		}
+		if !strings.EqualFold(sendErr.errlist[0].Error(), "503 5.1.2 Invalid from: <invalid-from@domain.tld>") {
+			t.Errorf("expected error: %q, but got %q",
+				"503 5.1.2 Invalid from: <invalid-from@domain.tld>", sendErr.errlist[0].Error())
+		}
+		if !strings.EqualFold(sendErr.errlist[1].Error(), "500 5.1.2 Error: reset failed") {
+			t.Errorf("expected error: %q, but got %q",
+				"500 5.1.2 Error: reset failed", sendErr.errlist[1].Error())
+		}
+	}
+
+	if err = client.Close(); err != nil {
+		t.Errorf("failed to close server connection: %s", err)
+	}
+}
+
+func TestClient_SendErrorToReset(t *testing.T) {
+	ctx, cancel := context.WithCancel(context.Background())
+	defer cancel()
+
+	serverPort := TestServerPortBase + 4
+	featureSet := "250-AUTH PLAIN\r\n250-8BITMIME\r\n250-DSN\r\n250 SMTPUTF8"
+	go func() {
+		if err := simpleSMTPServer(ctx, featureSet, true, serverPort); err != nil {
+			t.Errorf("failed to start test server: %s", err)
+			return
+		}
+	}()
+	time.Sleep(time.Millisecond * 300)
+
+	message := NewMsg()
+	if err := message.From("valid-from@domain.tld"); err != nil {
+		t.Errorf("failed to set FROM address: %s", err)
+		return
+	}
+	if err := message.To("invalid-to@domain.tld"); err != nil {
+		t.Errorf("failed to set TO address: %s", err)
+		return
+	}
+	message.Subject("Test subject")
+	message.SetBodyString(TypeTextPlain, "Test body")
+	message.SetMessageIDWithValue("this.is.a.message.id")
+
+	client, err := NewClient(TestServerAddr, WithPort(serverPort),
+		WithTLSPortPolicy(NoTLS), WithSMTPAuth(SMTPAuthPlain),
+		WithUsername("toni@tester.com"),
+		WithPassword("V3ryS3cr3t+"))
+	if err != nil {
+		t.Errorf("unable to create new client: %s", err)
+	}
+	if err = client.DialWithContext(context.Background()); err != nil {
+		t.Errorf("failed to dial to test server: %s", err)
+	}
+	if err = client.Send(message); err == nil {
+		t.Error("expected Send() to fail but didn't")
+	}
+
+	var sendErr *SendError
+	if !errors.As(err, &sendErr) {
+		t.Errorf("expected *SendError type as returned error, but got %T", sendErr)
+	}
+	if errors.As(err, &sendErr) {
+		if sendErr.IsTemp() {
+			t.Errorf("expected permanent error but IsTemp() returned true")
+		}
+		if sendErr.Reason != ErrSMTPRcptTo {
+			t.Errorf("expected ErrSMTPRcptTo error, but got %s", sendErr.Reason)
+		}
+		if !strings.EqualFold(sendErr.MessageID(), "<this.is.a.message.id>") {
+			t.Errorf("expected message ID: %q, but got %q", "<this.is.a.message.id>",
+				sendErr.MessageID())
+		}
+		if len(sendErr.errlist) != 2 {
+			t.Errorf("expected 2 errors, but got %d", len(sendErr.errlist))
+			return
+		}
+		if !strings.EqualFold(sendErr.errlist[0].Error(), "500 5.1.2 Invalid to: <invalid-to@domain.tld>") {
+			t.Errorf("expected error: %q, but got %q",
+				"500 5.1.2 Invalid to: <invalid-to@domain.tld>", sendErr.errlist[0].Error())
+		}
+		if !strings.EqualFold(sendErr.errlist[1].Error(), "500 5.1.2 Error: reset failed") {
+			t.Errorf("expected error: %q, but got %q",
+				"500 5.1.2 Error: reset failed", sendErr.errlist[1].Error())
+		}
+	}
+
+	if err = client.Close(); err != nil {
+		t.Errorf("failed to close server connection: %s", err)
+	}
+}
+
+func TestClient_SendErrorDataClose(t *testing.T) {
+	ctx, cancel := context.WithCancel(context.Background())
+	defer cancel()
+
+	serverPort := TestServerPortBase + 5
+	featureSet := "250-AUTH PLAIN\r\n250-8BITMIME\r\n250-DSN\r\n250 SMTPUTF8"
+	go func() {
+		if err := simpleSMTPServer(ctx, featureSet, false, serverPort); err != nil {
+			t.Errorf("failed to start test server: %s", err)
+			return
+		}
+	}()
+	time.Sleep(time.Millisecond * 300)
+
+	message := NewMsg()
+	if err := message.From("valid-from@domain.tld"); err != nil {
+		t.Errorf("failed to set FROM address: %s", err)
+		return
+	}
+	if err := message.To("valid-to@domain.tld"); err != nil {
+		t.Errorf("failed to set TO address: %s", err)
+		return
+	}
+	message.Subject("Test subject")
+	message.SetBodyString(TypeTextPlain, "DATA close should fail")
+	message.SetMessageIDWithValue("this.is.a.message.id")
+
+	client, err := NewClient(TestServerAddr, WithPort(serverPort),
+		WithTLSPortPolicy(NoTLS), WithSMTPAuth(SMTPAuthPlain),
+		WithUsername("toni@tester.com"),
+		WithPassword("V3ryS3cr3t+"))
+	if err != nil {
+		t.Errorf("unable to create new client: %s", err)
+	}
+	if err = client.DialWithContext(context.Background()); err != nil {
+		t.Errorf("failed to dial to test server: %s", err)
+	}
+	if err = client.Send(message); err == nil {
+		t.Error("expected Send() to fail but didn't")
+	}
+
+	var sendErr *SendError
+	if !errors.As(err, &sendErr) {
+		t.Errorf("expected *SendError type as returned error, but got %T", sendErr)
+	}
+	if errors.As(err, &sendErr) {
+		if sendErr.IsTemp() {
+			t.Errorf("expected permanent error but IsTemp() returned true")
+		}
+		if sendErr.Reason != ErrSMTPDataClose {
+			t.Errorf("expected ErrSMTPDataClose error, but got %s", sendErr.Reason)
+		}
+		if !strings.EqualFold(sendErr.MessageID(), "<this.is.a.message.id>") {
+			t.Errorf("expected message ID: %q, but got %q", "<this.is.a.message.id>",
+				sendErr.MessageID())
+		}
+	}
+
+	if err = client.Close(); err != nil {
+		t.Errorf("failed to close server connection: %s", err)
+	}
+}
+
+func TestClient_SendErrorDataWrite(t *testing.T) {
+	ctx, cancel := context.WithCancel(context.Background())
+	defer cancel()
+
+	serverPort := TestServerPortBase + 6
+	featureSet := "250-AUTH PLAIN\r\n250-8BITMIME\r\n250-DSN\r\n250 SMTPUTF8"
+	go func() {
+		if err := simpleSMTPServer(ctx, featureSet, false, serverPort); err != nil {
+			t.Errorf("failed to start test server: %s", err)
+			return
+		}
+	}()
+	time.Sleep(time.Millisecond * 300)
+
+	message := NewMsg()
+	if err := message.From("valid-from@domain.tld"); err != nil {
+		t.Errorf("failed to set FROM address: %s", err)
+		return
+	}
+	if err := message.To("valid-to@domain.tld"); err != nil {
+		t.Errorf("failed to set TO address: %s", err)
+		return
+	}
+	message.Subject("Test subject")
+	message.SetBodyString(TypeTextPlain, "DATA write should fail")
+	message.SetMessageIDWithValue("this.is.a.message.id")
+	message.SetGenHeader("X-Test-Header", "DATA write should fail")
+
+	client, err := NewClient(TestServerAddr, WithPort(serverPort),
+		WithTLSPortPolicy(NoTLS), WithSMTPAuth(SMTPAuthPlain),
+		WithUsername("toni@tester.com"),
+		WithPassword("V3ryS3cr3t+"))
+	if err != nil {
+		t.Errorf("unable to create new client: %s", err)
+	}
+	if err = client.DialWithContext(context.Background()); err != nil {
+		t.Errorf("failed to dial to test server: %s", err)
+	}
+	if err = client.Send(message); err == nil {
+		t.Error("expected Send() to fail but didn't")
+	}
+
+	var sendErr *SendError
+	if !errors.As(err, &sendErr) {
+		t.Errorf("expected *SendError type as returned error, but got %T", sendErr)
+	}
+	if errors.As(err, &sendErr) {
+		if sendErr.IsTemp() {
+			t.Errorf("expected permanent error but IsTemp() returned true")
+		}
+		if sendErr.Reason != ErrSMTPDataClose {
+			t.Errorf("expected ErrSMTPDataClose error, but got %s", sendErr.Reason)
+		}
+		if !strings.EqualFold(sendErr.MessageID(), "<this.is.a.message.id>") {
+			t.Errorf("expected message ID: %q, but got %q", "<this.is.a.message.id>",
+				sendErr.MessageID())
+		}
+	}
+}
+
+func TestClient_SendErrorReset(t *testing.T) {
+	ctx, cancel := context.WithCancel(context.Background())
+	defer cancel()
+
+	serverPort := TestServerPortBase + 7
+	featureSet := "250-AUTH PLAIN\r\n250-8BITMIME\r\n250-DSN\r\n250 SMTPUTF8"
+	go func() {
+		if err := simpleSMTPServer(ctx, featureSet, true, serverPort); err != nil {
+			t.Errorf("failed to start test server: %s", err)
+			return
+		}
+	}()
+	time.Sleep(time.Millisecond * 300)
+
+	message := NewMsg()
+	if err := message.From("valid-from@domain.tld"); err != nil {
+		t.Errorf("failed to set FROM address: %s", err)
+		return
+	}
+	if err := message.To("valid-to@domain.tld"); err != nil {
+		t.Errorf("failed to set TO address: %s", err)
+		return
+	}
+	message.Subject("Test subject")
+	message.SetBodyString(TypeTextPlain, "Test body")
+	message.SetMessageIDWithValue("this.is.a.message.id")
+
+	client, err := NewClient(TestServerAddr, WithPort(serverPort),
+		WithTLSPortPolicy(NoTLS), WithSMTPAuth(SMTPAuthPlain),
+		WithUsername("toni@tester.com"),
+		WithPassword("V3ryS3cr3t+"))
+	if err != nil {
+		t.Errorf("unable to create new client: %s", err)
+	}
+	if err = client.DialWithContext(context.Background()); err != nil {
+		t.Errorf("failed to dial to test server: %s", err)
+	}
+	if err = client.Send(message); err == nil {
+		t.Error("expected Send() to fail but didn't")
+	}
+
+	var sendErr *SendError
+	if !errors.As(err, &sendErr) {
+		t.Errorf("expected *SendError type as returned error, but got %T", sendErr)
+	}
+	if errors.As(err, &sendErr) {
+		if sendErr.IsTemp() {
+			t.Errorf("expected permanent error but IsTemp() returned true")
+		}
+		if sendErr.Reason != ErrSMTPReset {
+			t.Errorf("expected ErrSMTPReset error, but got %s", sendErr.Reason)
+		}
+		if !strings.EqualFold(sendErr.MessageID(), "<this.is.a.message.id>") {
+			t.Errorf("expected message ID: %q, but got %q", "<this.is.a.message.id>",
+				sendErr.MessageID())
+		}
+	}
+
+	if err = client.Close(); err != nil {
+		t.Errorf("failed to close server connection: %s", err)
+	}
+}
+
 // 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) {
@@ -1302,6 +1779,50 @@ func getTestConnection(auth bool) (*Client, error) {
 	return c, nil
 }
 
+// getTestConnectionNoTestPort takes environment variables (except the port) to establish a
+// connection to a real SMTP server to test all functionality that requires a connection
+func getTestConnectionNoTestPort(auth bool) (*Client, error) {
+	if os.Getenv("TEST_SKIP_ONLINE") != "" {
+		return nil, fmt.Errorf("env variable TEST_SKIP_ONLINE is set. Skipping online tests")
+	}
+	th := os.Getenv("TEST_HOST")
+	if th == "" {
+		return nil, fmt.Errorf("no TEST_HOST set")
+	}
+	sv := false
+	if sve := os.Getenv("TEST_TLS_SKIP_VERIFY"); sve != "" {
+		sv = true
+	}
+	c, err := NewClient(th)
+	if err != nil {
+		return c, err
+	}
+	c.tlsconfig.InsecureSkipVerify = sv
+	if auth {
+		st := os.Getenv("TEST_SMTPAUTH_TYPE")
+		if st != "" {
+			c.SetSMTPAuth(SMTPAuthType(st))
+		}
+		u := os.Getenv("TEST_SMTPAUTH_USER")
+		if u != "" {
+			c.SetUsername(u)
+		}
+		p := os.Getenv("TEST_SMTPAUTH_PASS")
+		if p != "" {
+			c.SetPassword(p)
+		}
+		// We don't want to log authentication data in tests
+		c.SetDebugLog(false)
+	}
+	if err := c.DialWithContext(context.Background()); err != nil {
+		return c, fmt.Errorf("connection to test server failed: %w", err)
+	}
+	if err := c.Close(); err != nil {
+		return c, fmt.Errorf("disconnect from test server failed: %w", err)
+	}
+	return c, nil
+}
+
 // getTestClient takes environment variables to establish a client without connecting
 // to the SMTP server
 func getTestClient(auth bool) (*Client, error) {
@@ -1357,7 +1878,14 @@ func getTestConnectionWithDSN(auth bool) (*Client, error) {
 	if th == "" {
 		return nil, fmt.Errorf("no TEST_HOST set")
 	}
-	c, err := NewClient(th, WithDSN())
+	tp := 25
+	if tps := os.Getenv("TEST_PORT"); tps != "" {
+		tpi, err := strconv.Atoi(tps)
+		if err == nil {
+			tp = tpi
+		}
+	}
+	c, err := NewClient(th, WithDSN(), WithPort(tp))
 	if err != nil {
 		return c, err
 	}
@@ -1494,3 +2022,155 @@ func (f faker) RemoteAddr() net.Addr             { return nil }
 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 }
+
+// simpleSMTPServer starts a simple TCP server that resonds to SMTP commands.
+// The provided featureSet represents in what the server responds to EHLO command
+// failReset controls if a RSET succeeds
+func simpleSMTPServer(ctx context.Context, featureSet string, failReset bool, port int) error {
+	listener, err := net.Listen(TestServerProto, fmt.Sprintf("%s:%d", TestServerAddr, port))
+	if err != nil {
+		return fmt.Errorf("unable to listen on %s://%s: %w", TestServerProto, TestServerAddr, err)
+	}
+
+	defer func() {
+		if err := listener.Close(); err != nil {
+			fmt.Printf("unable to close listener: %s\n", err)
+			os.Exit(1)
+		}
+	}()
+
+	for {
+		select {
+		case <-ctx.Done():
+			return nil
+		default:
+			connection, err := listener.Accept()
+			var opErr *net.OpError
+			if err != nil {
+				if errors.As(err, &opErr) && opErr.Temporary() {
+					continue
+				}
+				return fmt.Errorf("unable to accept connection: %w", err)
+			}
+			handleTestServerConnection(connection, featureSet, failReset)
+		}
+	}
+}
+
+func handleTestServerConnection(connection net.Conn, featureSet string, failReset bool) {
+	defer func() {
+		if err := connection.Close(); err != nil {
+			fmt.Printf("unable to close connection: %s\n", err)
+		}
+	}()
+
+	reader := bufio.NewReader(connection)
+	writer := bufio.NewWriter(connection)
+
+	writeLine := func(data string) error {
+		_, err := writer.WriteString(data + "\r\n")
+		if err != nil {
+			return fmt.Errorf("unable to write line: %w", err)
+		}
+		return writer.Flush()
+	}
+	writeOK := func() {
+		_ = writeLine("250 2.0.0 OK")
+	}
+
+	if err := writeLine("220 go-mail test server ready ESMTP"); err != nil {
+		fmt.Printf("unable to write to client: %s\n", err)
+		return
+	}
+
+	data, err := reader.ReadString('\n')
+	if err != nil {
+		fmt.Printf("unable to read from connection: %s\n", err)
+		return
+	}
+	if !strings.HasPrefix(data, "EHLO") && !strings.HasPrefix(data, "HELO") {
+		fmt.Printf("expected EHLO, got %q", data)
+		return
+	}
+	if err = writeLine("250-localhost.localdomain\r\n" + featureSet); err != nil {
+		fmt.Printf("unable to write to connection: %s\n", err)
+		return
+	}
+
+	for {
+		data, err = reader.ReadString('\n')
+		if err != nil {
+			if errors.Is(err, io.EOF) {
+				break
+			}
+			fmt.Println("Error reading data:", err)
+			break
+		}
+
+		var datastring string
+		data = strings.TrimSpace(data)
+		switch {
+		case strings.HasPrefix(data, "MAIL FROM:"):
+			from := strings.TrimPrefix(data, "MAIL FROM:")
+			from = strings.ReplaceAll(from, "BODY=8BITMIME", "")
+			from = strings.ReplaceAll(from, "SMTPUTF8", "")
+			from = strings.TrimSpace(from)
+			if !strings.EqualFold(from, "<valid-from@domain.tld>") {
+				_ = writeLine(fmt.Sprintf("503 5.1.2 Invalid from: %s", from))
+				break
+			}
+			writeOK()
+		case strings.HasPrefix(data, "RCPT TO:"):
+			to := strings.TrimPrefix(data, "RCPT TO:")
+			to = strings.TrimSpace(to)
+			if !strings.EqualFold(to, "<valid-to@domain.tld>") {
+				_ = writeLine(fmt.Sprintf("500 5.1.2 Invalid to: %s", to))
+				break
+			}
+			writeOK()
+		case strings.HasPrefix(data, "AUTH PLAIN"):
+			auth := strings.TrimPrefix(data, "AUTH PLAIN ")
+			if !strings.EqualFold(auth, "AHRvbmlAdGVzdGVyLmNvbQBWM3J5UzNjcjN0Kw==") {
+				_ = writeLine("535 5.7.8 Error: authentication failed")
+				break
+			}
+			_ = writeLine("235 2.7.0 Authentication successful")
+		case strings.EqualFold(data, "DATA"):
+			_ = writeLine("354 End data with <CR><LF>.<CR><LF>")
+			for {
+				ddata, derr := reader.ReadString('\n')
+				if derr != nil {
+					fmt.Printf("failed to read DATA data from connection: %s\n", derr)
+					break
+				}
+				ddata = strings.TrimSpace(ddata)
+				if strings.EqualFold(ddata, "DATA write should fail") {
+					_ = writeLine("500 5.0.0 Error during DATA transmission")
+					break
+				}
+				if ddata == "." {
+					if strings.Contains(datastring, "DATA close should fail") {
+						_ = writeLine("500 5.0.0 Error during DATA closing")
+						break
+					}
+					_ = writeLine("250 2.0.0 Ok: queued as 1234567890")
+					break
+				}
+				datastring += ddata + "\n"
+			}
+		case strings.EqualFold(data, "noop"),
+			strings.EqualFold(data, "vrfy"):
+			writeOK()
+		case strings.EqualFold(data, "rset"):
+			if failReset {
+				_ = writeLine("500 5.1.2 Error: reset failed")
+				break
+			}
+			writeOK()
+		case strings.EqualFold(data, "quit"):
+			_ = writeLine("221 2.0.0 Bye")
+		default:
+			_ = writeLine("500 5.5.2 Error: bad syntax")
+		}
+	}
+}

dummy-chain-cert.pem

@@ -0,0 +1,62 @@
+-----BEGIN CERTIFICATE-----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+1QIDAQABo0IwQDAdBgNVHQ4EFgQUS8+HouVQ94SdgI3kV3L8Jm53P6YwHwYDVR0j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+-----END CERTIFICATE-----
+-----BEGIN CERTIFICATE-----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=
+-----END CERTIFICATE-----

dummy-child-key.pem

@@ -0,0 +1,52 @@
+-----BEGIN PRIVATE KEY-----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+-----END PRIVATE KEY-----

msg.go

@@ -7,8 +7,7 @@ package mail
 import (
 	"bytes"
 	"context"
-	"crypto/rsa"
-	"crypto/x509"
+	"crypto/tls"
 	"embed"
 	"errors"
 	"fmt"
@@ -208,8 +207,8 @@ func WithNoDefaultUserAgent() MsgOption {
 }
 
 // SignWithSMime configures the Msg to be signed with S/MIME
-func (m *Msg) SignWithSMime(privateKey *rsa.PrivateKey, certificate *x509.Certificate) error {
-	sMime, err := NewSMime(privateKey, certificate)
+func (m *Msg) SignWithSMime(keyPair *tls.Certificate) error {
+	sMime, err := newSMime(keyPair)
 	if err != nil {
 		return err
 	}
@@ -482,8 +481,8 @@ func (m *Msg) SetMessageID() {
 	if err != nil {
 		hostname = "localhost.localdomain"
 	}
-	randNumPrimary, _ := randNum(100000000)
-	randNumSecondary, _ := randNum(10000)
+	randNumPrimary := randNum(100000000)
+	randNumSecondary := randNum(10000)
 	randString, _ := randomStringSecure(17)
 	procID := os.Getpid() * randNumSecondary
 	messageID := fmt.Sprintf("%d.%d%d.%s@%s", procID, randNumPrimary, randNumSecondary,
@@ -491,6 +490,17 @@ func (m *Msg) SetMessageID() {
 	m.SetMessageIDWithValue(messageID)
 }
 
+// GetMessageID returns the message ID of the Msg as string value. If no message ID
+// is set, an empty string will be returned
+func (m *Msg) GetMessageID() string {
+	if msgidheader, ok := m.genHeader[HeaderMessageID]; ok {
+		if len(msgidheader) > 0 {
+			return msgidheader[0]
+		}
+	}
+	return ""
+}
+
 // SetMessageIDWithValue sets the message id for the mail
 func (m *Msg) SetMessageIDWithValue(messageID string) {
 	m.SetGenHeader(HeaderMessageID, fmt.Sprintf("<%s>", messageID))
@@ -985,28 +995,31 @@ func (m *Msg) applyMiddlewares(msg *Msg) *Msg {
 
 // signMessage sign the Msg with S/MIME
 func (m *Msg) signMessage(msg *Msg) (*Msg, error) {
-	currentPart := m.GetParts()[0]
-	currentPart.SetEncoding(EncodingUSASCII)
-	currentPart.SetContentType(TypeTextPlain)
-	content, err := currentPart.GetContent()
+	signedPart := msg.GetParts()[0]
+	body, err := signedPart.GetContent()
 	if err != nil {
-		return nil, errors.New("failed to extract content from part")
+		return nil, err
 	}
 
-	signedContent, err := m.sMime.Sign(content)
+	signaturePart, err := m.createSignaturePart(signedPart.GetEncoding(), signedPart.GetContentType(), signedPart.GetCharset(), body)
 	if err != nil {
-		return nil, errors.New("failed to sign message")
+		return nil, err
 	}
 
-	signedPart := msg.newPart(
-		typeSMimeSigned,
-		WithPartEncoding(EncodingB64),
-		WithContentDisposition(DispositionSMime),
-	)
-	signedPart.SetContent(*signedContent)
-	msg.parts = append(msg.parts, signedPart)
+	m.parts = append(m.parts, signaturePart)
 
-	return msg, nil
+	return m, err
+}
+
+func (m *Msg) createSignaturePart(encoding Encoding, contentType ContentType, charSet Charset, body []byte) (*Part, error) {
+	message := m.sMime.createMessage(encoding, contentType, charSet, body)
+	signaturePart := m.newPart(typeSMimeSigned, WithPartEncoding(EncodingB64), WithSMimeSinging())
+
+	if err := m.sMime.sign(signaturePart, message); err != nil {
+		return nil, err
+	}
+
+	return signaturePart, nil
 }
 
 // WriteTo writes the formated Msg into a give io.Writer and satisfies the io.WriteTo interface
@@ -1014,7 +1027,7 @@ func (m *Msg) WriteTo(writer io.Writer) (int64, error) {
 	mw := &msgWriter{writer: writer, charset: m.charset, encoder: m.encoder}
 	msg := m.applyMiddlewares(m)
 
-	if m.sMime != nil {
+	if m.hasSMime() {
 		signedMsg, err := m.signMessage(msg)
 		if err != nil {
 			return 0, err
@@ -1210,7 +1223,7 @@ func (m *Msg) hasAlt() bool {
 			count++
 		}
 	}
-	return count > 1 && m.pgptype == 0
+	return count > 1 && m.pgptype == 0 && !m.hasSMime()
 }
 
 // hasMixed returns true if the Msg has mixed parts

msg_nowin_test.go

@@ -61,3 +61,25 @@ func TestMsg_WriteToSendmail(t *testing.T) {
 		t.Errorf("WriteToSendmail failed: %s", err)
 	}
 }
+
+func TestMsg_WriteToTempFileFailed(t *testing.T) {
+	m := NewMsg()
+	_ = m.From("Toni Tester <tester@example.com>")
+	_ = m.To("Ellenor Tester <ellinor@example.com>")
+	m.SetBodyString(TypeTextPlain, "This is a test")
+
+	curTmpDir := os.Getenv("TMPDIR")
+	defer func() {
+		if err := os.Setenv("TMPDIR", curTmpDir); err != nil {
+			t.Errorf("failed to set TMPDIR environment variable: %s", err)
+		}
+	}()
+
+	if err := os.Setenv("TMPDIR", "/invalid/directory/that/does/not/exist"); err != nil {
+		t.Errorf("failed to set TMPDIR environment variable: %s", err)
+	}
+	_, err := m.WriteToTempFile()
+	if err == nil {
+		t.Errorf("WriteToTempFile() did not fail as expected")
+	}
+}

msg_test.go

@@ -786,13 +786,11 @@ func TestMsg_SetMessageIDWithValue(t *testing.T) {
 // TestMsg_SetMessageIDRandomness tests the randomness of Msg.SetMessageID methods
 func TestMsg_SetMessageIDRandomness(t *testing.T) {
 	var mids []string
-	for i := 0; i < 100; i++ {
+	for i := 0; i < 50_000; i++ {
 		m := NewMsg()
 		m.SetMessageID()
-		mid := m.GetGenHeader(HeaderMessageID)
-		if len(mid) > 0 {
-			mids = append(mids, mid[0])
-		}
+		mid := m.GetMessageID()
+		mids = append(mids, mid)
 	}
 	c := make(map[string]int)
 	for i := range mids {
@@ -805,6 +803,21 @@ func TestMsg_SetMessageIDRandomness(t *testing.T) {
 	}
 }
 
+func TestMsg_GetMessageID(t *testing.T) {
+	expected := "this.is.a.message.id"
+	msg := NewMsg()
+	msg.SetMessageIDWithValue(expected)
+	val := msg.GetMessageID()
+	if !strings.EqualFold(val, fmt.Sprintf("<%s>", expected)) {
+		t.Errorf("GetMessageID() failed. Expected: %s, got: %s", fmt.Sprintf("<%s>", expected), val)
+	}
+	msg.genHeader[HeaderMessageID] = nil
+	val = msg.GetMessageID()
+	if val != "" {
+		t.Errorf("GetMessageID() failed. Expected empty string, got: %s", val)
+	}
+}
+
 // TestMsg_FromFormat tests the FromFormat and EnvelopeFrom methods for the Msg object
 func TestMsg_FromFormat(t *testing.T) {
 	tests := []struct {
@@ -1894,6 +1907,23 @@ func TestMsg_hasAlt(t *testing.T) {
 	}
 }
 
+// TestMsg_hasAlt tests the hasAlt() method of the Msg with active S/MIME
+func TestMsg_hasAltWithSMime(t *testing.T) {
+	keyPair, err := getDummyCertificate()
+	if err != nil {
+		t.Errorf("failed to load dummy certificate. Cause: %v", err)
+	}
+	m := NewMsg()
+	m.SetBodyString(TypeTextPlain, "Plain")
+	m.AddAlternativeString(TypeTextHTML, "<b>HTML</b>")
+	if err := m.SignWithSMime(keyPair); err != nil {
+		t.Errorf("set of certificate was not successful")
+	}
+	if m.hasAlt() {
+		t.Errorf("mail has alternative parts and S/MIME is active, but hasAlt() returned true")
+	}
+}
+
 // TestMsg_hasRelated tests the hasRelated() method of the Msg
 func TestMsg_hasRelated(t *testing.T) {
 	m := NewMsg()
@@ -3233,32 +3263,33 @@ func TestNewMsgWithNoDefaultUserAgent(t *testing.T) {
 	}
 }
 
-// TestWithSMimeSinging_ValidPrivateKey tests WithSMimeSinging with given privateKey
-func TestWithSMimeSinging_ValidPrivateKey(t *testing.T) {
-	privateKey, err := getDummyPrivateKey()
+// TestSignWithSMime_ValidKeyPair tests WithSMimeSinging with given key pair
+func TestSignWithSMime_ValidKeyPair(t *testing.T) {
+	keyPair, err := getDummyCertificate()
 	if err != nil {
-		t.Errorf("failed to load dummy private key: %s", err)
+		t.Errorf("failed to load dummy certificate. Cause: %v", err)
 	}
-	certificate, err := getDummyCertificate(privateKey)
-	if err != nil {
-		t.Errorf("failed to load dummy certificate: %s", err)
-	}
-
 	m := NewMsg()
-	if err := m.SignWithSMime(privateKey, certificate); err != nil {
+	if err := m.SignWithSMime(keyPair); err != nil {
 		t.Errorf("failed to set sMime. Cause: %v", err)
 	}
-	if m.sMime.privateKey != privateKey {
-		t.Errorf("WithSMimeSinging. Expected %v, got: %v", privateKey, m.sMime.privateKey)
+	if m.sMime.privateKey == nil {
+		t.Errorf("WithSMimeSinging() - no private key is given")
+	}
+	if m.sMime.certificate == nil {
+		t.Errorf("WithSMimeSinging() - no certificate is given")
+	}
+	if len(m.sMime.parentCertificates) != len(keyPair.Certificate[:1]) {
+		t.Errorf("WithSMimeSinging() - no certificate is given")
 	}
 }
 
-// TestWithSMimeSinging_InvalidPrivateKey tests WithSMimeSinging with given invalid privateKey
-func TestWithSMimeSinging_InvalidPrivateKey(t *testing.T) {
+// TestSignWithSMime_InvalidKeyPair tests WithSMimeSinging with given invalid key pair
+func TestSignWithSMime_InvalidKeyPair(t *testing.T) {
 	m := NewMsg()
 
-	err := m.SignWithSMime(nil, nil)
-	if !errors.Is(err, ErrInvalidPrivateKey) {
+	err := m.SignWithSMime(nil)
+	if !errors.Is(err, ErrInvalidKeyPair) {
 		t.Errorf("failed to check sMimeAuthConfig values correctly: %s", err)
 	}
 }
@@ -3290,3 +3321,84 @@ func FuzzMsg_From(f *testing.F) {
 		m.Reset()
 	})
 }
+
+// TestMsg_createSignaturePart tests the Msg.createSignaturePart method
+func TestMsg_createSignaturePart(t *testing.T) {
+	keyPair, err := getDummyCertificate()
+	if err != nil {
+		t.Errorf("failed to load dummy certificate. Cause: %v", err)
+	}
+	m := NewMsg()
+	if err := m.SignWithSMime(keyPair); err != nil {
+		t.Errorf("set of certificate was not successful")
+	}
+	body := []byte("This is the body")
+	part, err := m.createSignaturePart(EncodingQP, TypeTextPlain, CharsetUTF7, body)
+	if err != nil {
+		t.Errorf("createSignaturePart() method failed.")
+	}
+
+	if part.GetEncoding() != EncodingB64 {
+		t.Errorf("createSignaturePart() method failed. Expected encoding: %s, got: %s", EncodingB64, part.GetEncoding())
+	}
+	if part.GetContentType() != typeSMimeSigned {
+		t.Errorf("createSignaturePart() method failed. Expected content type: %s, got: %s", typeSMimeSigned, part.GetContentType())
+	}
+	if part.GetCharset() != CharsetUTF8 {
+		t.Errorf("createSignaturePart() method failed. Expected charset: %s, got: %s", CharsetUTF8, part.GetCharset())
+	}
+	if content, err := part.GetContent(); err != nil || len(content) == len(body) {
+		t.Errorf("createSignaturePart() method failed. Expected content should not be equal: %s, got: %s", body, part.GetEncoding())
+	}
+}
+
+// TestMsg_signMessage tests the Msg.signMessage method
+func TestMsg_signMessage(t *testing.T) {
+	keyPair, err := getDummyCertificate()
+	if err != nil {
+		t.Errorf("failed to load dummy certificate. Cause: %v", err)
+	}
+	body := []byte("This is the body")
+	m := NewMsg()
+	m.SetBodyString(TypeTextPlain, string(body))
+	if err := m.SignWithSMime(keyPair); err != nil {
+		t.Errorf("set of certificate was not successful")
+	}
+	msg, err := m.signMessage(m)
+	if err != nil {
+		t.Errorf("createSignaturePart() method failed.")
+	}
+
+	parts := msg.GetParts()
+	if len(parts) != 2 {
+		t.Errorf("createSignaturePart() method failed. Expected 2 parts, got: %d", len(parts))
+	}
+
+	signedPart := parts[0]
+	if signedPart.GetEncoding() != EncodingQP {
+		t.Errorf("createSignaturePart() method failed. Expected encoding: %s, got: %s", EncodingB64, signedPart.GetEncoding())
+	}
+	if signedPart.GetContentType() != TypeTextPlain {
+		t.Errorf("createSignaturePart() method failed. Expected content type: %s, got: %s", typeSMimeSigned, signedPart.GetContentType())
+	}
+	if signedPart.GetCharset() != CharsetUTF8 {
+		t.Errorf("createSignaturePart() method failed. Expected charset: %s, got: %s", CharsetUTF8, signedPart.GetCharset())
+	}
+	if content, err := signedPart.GetContent(); err != nil || len(content) != len(body) {
+		t.Errorf("createSignaturePart() method failed. Expected content should be equal: %s, got: %s", body, content)
+	}
+
+	signaturePart := parts[1]
+	if signaturePart.GetEncoding() != EncodingB64 {
+		t.Errorf("createSignaturePart() method failed. Expected encoding: %s, got: %s", EncodingB64, signaturePart.GetEncoding())
+	}
+	if signaturePart.GetContentType() != typeSMimeSigned {
+		t.Errorf("createSignaturePart() method failed. Expected content type: %s, got: %s", typeSMimeSigned, signaturePart.GetContentType())
+	}
+	if signaturePart.GetCharset() != CharsetUTF8 {
+		t.Errorf("createSignaturePart() method failed. Expected charset: %s, got: %s", CharsetUTF8, signaturePart.GetCharset())
+	}
+	if content, err := signaturePart.GetContent(); err != nil || len(content) == len(body) {
+		t.Errorf("createSignaturePart() method failed. Expected content should not be equal: %s, got: %s", body, signaturePart.GetEncoding())
+	}
+}

msgwriter.go

@@ -100,7 +100,7 @@ func (mw *msgWriter) writeMsg(msg *Msg) {
 		mw.startMP(MIMERelated, msg.boundary)
 		mw.writeString(DoubleNewLine)
 	}
-	if msg.hasAlt() && !msg.hasSMime() {
+	if msg.hasAlt() {
 		mw.startMP(MIMEAlternative, msg.boundary)
 		mw.writeString(DoubleNewLine)
 	}
@@ -241,7 +241,7 @@ func (mw *msgWriter) addFiles(files []*File, isAttachment bool) {
 		}
 
 		if mw.err == nil {
-			mw.writeBody(file.Writer, encoding)
+			mw.writeBody(file.Writer, encoding, false)
 		}
 	}
 }
@@ -273,7 +273,7 @@ func (mw *msgWriter) writePart(part *Part, charset Charset) {
 		mimeHeader.Add(string(HeaderContentTransferEnc), contentTransferEnc)
 		mw.newPart(mimeHeader)
 	}
-	mw.writeBody(part.writeFunc, part.encoding)
+	mw.writeBody(part.writeFunc, part.encoding, part.smime)
 }
 
 // writeString writes a string into the msgWriter's io.Writer interface
@@ -322,7 +322,7 @@ func (mw *msgWriter) writeHeader(key Header, values ...string) {
 }
 
 // writeBody writes an io.Reader into an io.Writer using provided Encoding
-func (mw *msgWriter) writeBody(writeFunc func(io.Writer) (int64, error), encoding Encoding) {
+func (mw *msgWriter) writeBody(writeFunc func(io.Writer) (int64, error), encoding Encoding, singingWithSMime bool) {
 	var writer io.Writer
 	var encodedWriter io.WriteCloser
 	var n int64
@@ -337,12 +337,11 @@ func (mw *msgWriter) writeBody(writeFunc func(io.Writer) (int64, error), encodin
 	lineBreaker := Base64LineBreaker{}
 	lineBreaker.out = &writeBuffer
 
-	switch encoding {
-	case EncodingQP:
+	if encoding == EncodingQP {
 		encodedWriter = quotedprintable.NewWriter(&writeBuffer)
-	case EncodingB64:
+	} else if encoding == EncodingB64 && !singingWithSMime {
 		encodedWriter = base64.NewEncoder(base64.StdEncoding, &lineBreaker)
-	case NoEncoding:
+	} else if encoding == NoEncoding {
 		_, err = writeFunc(&writeBuffer)
 		if err != nil {
 			mw.err = fmt.Errorf("bodyWriter function: %w", err)
@@ -355,7 +354,7 @@ func (mw *msgWriter) writeBody(writeFunc func(io.Writer) (int64, error), encodin
 			mw.bytesWritten += n
 		}
 		return
-	default:
+	} else {
 		encodedWriter = quotedprintable.NewWriter(writer)
 	}
 

msgwriter_test.go

@@ -154,3 +154,26 @@ func TestMsgWriter_writeMsg_PGP(t *testing.T) {
 		t.Errorf("writeMsg failed. Expected PGP encoding header but didn't find it in message output")
 	}
 }
+
+// TestMsgWriter_writeMsg_SMime tests the writeMsg method of the msgWriter with S/MIME types set
+func TestMsgWriter_writeMsg_SMime(t *testing.T) {
+	keyPair, err := getDummyCertificate()
+	if err != nil {
+		t.Errorf("failed to load dummy certificate. Cause: %v", err)
+	}
+	m := NewMsg()
+	if err := m.SignWithSMime(keyPair); err != nil {
+		t.Errorf("set of certificate was not successful")
+	}
+	_ = m.From(`"Toni Tester" <test@example.com>`)
+	_ = m.To(`"Toni Receiver" <receiver@example.com>`)
+	m.Subject("This is a subject")
+	m.SetBodyString(TypeTextPlain, "This is the body")
+	buf := bytes.Buffer{}
+	mw := &msgWriter{writer: &buf, charset: CharsetUTF8, encoder: mime.QEncoding}
+	mw.writeMsg(m)
+	ms := buf.String()
+	if !strings.Contains(ms, `multipart/signed; protocol="application/pkcs7-signature"; micalg=sha256;`) {
+		t.Errorf("writeMsg failed. Expected PGP encoding header but didn't find it in message output")
+	}
+}

part_test.go

@@ -275,6 +275,7 @@ func TestPart_IsSMimeSigned(t *testing.T) {
 	for _, tt := range tests {
 		t.Run(tt.name, func(t *testing.T) {
 			m := NewMsg()
+			m.SetBodyString(TypeTextPlain, "This is a body!")
 			pl, err := getPartList(m)
 			if err != nil {
 				t.Errorf("failed: %s", err)

random.go

@@ -7,8 +7,6 @@ package mail
 import (
 	"crypto/rand"
 	"encoding/binary"
-	"fmt"
-	"math/big"
 	"strings"
 )
 
@@ -52,23 +50,3 @@ func randomStringSecure(length int) (string, error) {
 
 	return randString.String(), nil
 }
-
-// randNum returns a random number with a maximum value of length
-func randNum(length int) (int, error) {
-	if length <= 0 {
-		return 0, fmt.Errorf("provided number is <= 0: %d", length)
-	}
-	length64 := big.NewInt(int64(length))
-	if !length64.IsUint64() {
-		return 0, fmt.Errorf("big.NewInt() generation returned negative value: %d", length64)
-	}
-	randNum64, err := rand.Int(rand.Reader, length64)
-	if err != nil {
-		return 0, err
-	}
-	randomNum := int(randNum64.Int64())
-	if randomNum < 0 {
-		return 0, fmt.Errorf("generated random number does not fit as int64: %d", randNum64)
-	}
-	return randomNum, nil
-}

random_119.go

@@ -0,0 +1,22 @@
+// SPDX-FileCopyrightText: 2022-2023 The go-mail Authors
+//
+// SPDX-License-Identifier: MIT
+
+//go:build go1.19 && !go1.20
+// +build go1.19,!go1.20
+
+package mail
+
+import (
+	"math/rand"
+	"time"
+)
+
+// randNum returns a random number with a maximum value of length
+func randNum(maxval int) int {
+	if maxval <= 0 {
+		return 0
+	}
+	rand.Seed(time.Now().UnixNano())
+	return rand.Intn(maxval)
+}

random_121.go

@@ -0,0 +1,20 @@
+// SPDX-FileCopyrightText: 2022-2023 The go-mail Authors
+//
+// SPDX-License-Identifier: MIT
+
+//go:build go1.20 && !go1.22
+// +build go1.20,!go1.22
+
+package mail
+
+import (
+	"math/rand"
+)
+
+// randNum returns a random number with a maximum value of length
+func randNum(maxval int) int {
+	if maxval <= 0 {
+		return 0
+	}
+	return rand.Intn(maxval)
+}

random_122.go

@@ -0,0 +1,22 @@
+// SPDX-FileCopyrightText: 2022-2023 The go-mail Authors
+//
+// SPDX-License-Identifier: MIT
+
+//go:build go1.22
+// +build go1.22
+
+package mail
+
+import (
+	"math/rand/v2"
+)
+
+// randNum returns a random number with a maximum value of maxval.
+// go-mail compiled with Go 1.22+ will make use of the novel math/rand/v2 interface
+// Older versions of Go will use math/rand
+func randNum(maxval int) int {
+	if maxval <= 0 {
+		return 0
+	}
+	return rand.IntN(maxval)
+}

random_test.go

@@ -55,16 +55,17 @@ func TestRandomNum(t *testing.T) {
 
 	for _, tc := range tt {
 		t.Run(tc.testName, func(t *testing.T) {
-			rn, err := randNum(tc.max)
-			if err != nil {
-				t.Errorf("random number generation failed: %s", err)
-			}
-			if rn < 0 {
-				t.Errorf("random number generation failed: %d is smaller than zero", rn)
-			}
+			rn := randNum(tc.max)
 			if rn > tc.max {
 				t.Errorf("random number generation failed: %d is bigger than given value %d", rn, tc.max)
 			}
 		})
 	}
 }
+
+func TestRandomNumZero(t *testing.T) {
+	rn := randNum(0)
+	if rn != 0 {
+		t.Errorf("random number generation failed: %d is not zero", rn)
+	}
+}

senderror.go

@@ -56,10 +56,11 @@ const (
 
 // SendError is an error wrapper for delivery errors of the Msg
 type SendError struct {
-	Reason  SendErrReason
-	isTemp  bool
+	affectedMsg *Msg
 	errlist     []error
+	isTemp      bool
 	rcpt        []string
+	Reason      SendErrReason
 }
 
 // SendErrReason represents a comparable reason on why the delivery failed
@@ -92,6 +93,11 @@ func (e *SendError) Error() string {
 			}
 		}
 	}
+	if e.affectedMsg != nil && e.affectedMsg.GetMessageID() != "" {
+		errMessage.WriteString(", affected message ID: ")
+		errMessage.WriteString(e.affectedMsg.GetMessageID())
+	}
+
 	return errMessage.String()
 }
 
@@ -112,6 +118,23 @@ func (e *SendError) IsTemp() bool {
 	return e.isTemp
 }
 
+// MessageID returns the message ID of the affected Msg that caused the error
+// If no message ID was set for the Msg, an empty string will be returned
+func (e *SendError) MessageID() string {
+	if e == nil || e.affectedMsg == nil {
+		return ""
+	}
+	return e.affectedMsg.GetMessageID()
+}
+
+// Msg returns the pointer to the affected message that caused the error
+func (e *SendError) Msg() *Msg {
+	if e == nil || e.affectedMsg == nil {
+		return nil
+	}
+	return e.affectedMsg
+}
+
 // String implements the Stringer interface for the SendErrReason
 func (r SendErrReason) String() string {
 	switch r {

senderror_test.go

@@ -83,7 +83,96 @@ func TestSendError_IsTemp(t *testing.T) {
 	}
 }
 
+func TestSendError_IsTempNil(t *testing.T) {
+	var se *SendError
+	if se.IsTemp() {
+		t.Error("expected false on nil-senderror")
+	}
+}
+
+func TestSendError_MessageID(t *testing.T) {
+	var se *SendError
+	err := returnSendError(ErrAmbiguous, false)
+	if !errors.As(err, &se) {
+		t.Errorf("error mismatch, expected error to be of type *SendError")
+		return
+	}
+	if errors.As(err, &se) {
+		if se.MessageID() == "" {
+			t.Errorf("sendError expected message-id, but got empty string")
+		}
+		if !strings.EqualFold(se.MessageID(), "<this.is.a.message.id>") {
+			t.Errorf("sendError message-id expected: %s, but got: %s", "<this.is.a.message.id>",
+				se.MessageID())
+		}
+	}
+}
+
+func TestSendError_MessageIDNil(t *testing.T) {
+	var se *SendError
+	if se.MessageID() != "" {
+		t.Error("expected empty string on nil-senderror")
+	}
+}
+
+func TestSendError_Msg(t *testing.T) {
+	var se *SendError
+	err := returnSendError(ErrAmbiguous, false)
+	if !errors.As(err, &se) {
+		t.Errorf("error mismatch, expected error to be of type *SendError")
+		return
+	}
+	if errors.As(err, &se) {
+		if se.Msg() == nil {
+			t.Errorf("sendError expected msg pointer, but got nil")
+		}
+		from := se.Msg().GetFromString()
+		if len(from) == 0 {
+			t.Errorf("sendError expected msg from, but got empty string")
+			return
+		}
+		if !strings.EqualFold(from[0], "<toni.tester@domain.tld>") {
+			t.Errorf("sendError message from expected: %s, but got: %s", "<toni.tester@domain.tld>",
+				from[0])
+		}
+	}
+}
+
+func TestSendError_MsgNil(t *testing.T) {
+	var se *SendError
+	if se.Msg() != nil {
+		t.Error("expected nil on nil-senderror")
+	}
+}
+
+func TestSendError_IsFail(t *testing.T) {
+	err1 := returnSendError(ErrAmbiguous, false)
+	err2 := returnSendError(ErrSMTPMailFrom, false)
+	if errors.Is(err1, err2) {
+		t.Errorf("error mismatch, ErrAmbiguous should not be equal to ErrSMTPMailFrom")
+	}
+}
+
+func TestSendError_ErrorMulti(t *testing.T) {
+	expected := `ambiguous reason, check Msg.SendError for message specific reasons, ` +
+		`affected recipient(s): <email1@domain.tld>, <email2@domain.tld>`
+	err := &SendError{
+		Reason: ErrAmbiguous, isTemp: false, affectedMsg: nil,
+		rcpt: []string{"<email1@domain.tld>", "<email2@domain.tld>"},
+	}
+	if err.Error() != expected {
+		t.Errorf("error mismatch, expected: %s, got: %s", expected, err.Error())
+	}
+}
+
 // 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}
+	message := NewMsg()
+	_ = message.From("toni.tester@domain.tld")
+	_ = message.To("tina.tester@domain.tld")
+	message.Subject("This is the subject")
+	message.SetBodyString(TypeTextPlain, "This is the message body")
+	message.SetMessageIDWithValue("this.is.a.message.id")
+
+	return &SendError{Reason: r, isTemp: t, affectedMsg: message}
 }

sime.go

@@ -1,18 +1,20 @@
 package mail
 
 import (
+	"bytes"
 	"crypto/rsa"
+	"crypto/tls"
 	"crypto/x509"
+	"encoding/pem"
 	"errors"
+	"fmt"
 	"go.mozilla.org/pkcs7"
+	"strings"
 )
 
 var (
-	// ErrInvalidPrivateKey should be used if private key is invalid
-	ErrInvalidPrivateKey = errors.New("invalid private key")
-
-	// ErrInvalidCertificate should be used if certificate is invalid
-	ErrInvalidCertificate = errors.New("invalid certificate")
+	// ErrInvalidKeyPair should be used if key pair is invalid
+	ErrInvalidKeyPair = errors.New("invalid key pair")
 
 	// ErrCouldNotInitialize should be used if the signed data could not initialize
 	ErrCouldNotInitialize = errors.New("could not initialize signed data")
@@ -22,49 +24,136 @@ var (
 
 	// ErrCouldNotFinishSigning should be used if the signing could not be finished
 	ErrCouldNotFinishSigning = errors.New("could not finish signing")
+
+	// ErrCouldNoEncodeToPEM should be used if the signature could not be encoded to PEM
+	ErrCouldNoEncodeToPEM = errors.New("could not encode to PEM")
 )
 
 // SMime is used to sign messages with S/MIME
 type SMime struct {
 	privateKey         *rsa.PrivateKey
 	certificate        *x509.Certificate
+	parentCertificates []*x509.Certificate
 }
 
-// NewSMime construct a new instance of SMime with a provided *rsa.PrivateKey
-func NewSMime(privateKey *rsa.PrivateKey, certificate *x509.Certificate) (*SMime, error) {
-	if privateKey == nil {
-		return nil, ErrInvalidPrivateKey
+// NewSMime construct a new instance of SMime with a provided *tls.Certificate
+func newSMime(keyPair *tls.Certificate) (*SMime, error) {
+	if keyPair == nil {
+		return nil, ErrInvalidKeyPair
 	}
 
-	if certificate == nil {
-		return nil, ErrInvalidCertificate
+	parentCertificates := make([]*x509.Certificate, 0)
+	for _, cert := range keyPair.Certificate[1:] {
+		c, err := x509.ParseCertificate(cert)
+		if err != nil {
+			return nil, err
+		}
+		parentCertificates = append(parentCertificates, c)
 	}
 
 	return &SMime{
-		privateKey:  privateKey,
-		certificate: certificate,
+		privateKey:         keyPair.PrivateKey.(*rsa.PrivateKey),
+		certificate:        keyPair.Leaf,
+		parentCertificates: parentCertificates,
 	}, nil
 }
 
-// Sign the content with the given privateKey of the method NewSMime
-func (sm *SMime) Sign(content []byte) (*string, error) {
-	toBeSigned, err := pkcs7.NewSignedData(content)
+// sign with the S/MIME method the message of the actual *Part
+func (sm *SMime) sign(signaturePart *Part, message string) error {
+	lines := parseLines([]byte(message))
+	toBeSigned := lines.bytesFromLines([]byte("\r\n"))
 
-	toBeSigned.SetDigestAlgorithm(pkcs7.OIDDigestAlgorithmSHA256)
+	tmp, err := pkcs7.NewSignedData(toBeSigned)
+	tmp.SetDigestAlgorithm(pkcs7.OIDDigestAlgorithmSHA256)
 	if err != nil {
-		return nil, ErrCouldNotInitialize
+		return ErrCouldNotInitialize
 	}
 
-	if err = toBeSigned.AddSigner(sm.certificate, sm.privateKey, pkcs7.SignerInfoConfig{}); err != nil {
-		return nil, ErrCouldNotAddSigner
+	if err = tmp.AddSignerChain(sm.certificate, sm.privateKey, sm.parentCertificates, pkcs7.SignerInfoConfig{}); err != nil {
+		return ErrCouldNotAddSigner
 	}
 
-	signed, err := toBeSigned.Finish()
+	signatureDER, err := tmp.Finish()
 	if err != nil {
-		return nil, ErrCouldNotFinishSigning
+		return ErrCouldNotFinishSigning
 	}
 
-	signedData := string(signed)
-
-	return &signedData, nil
+	pemMsg, err := encodeToPEM(signatureDER)
+	if err != nil {
+		return ErrCouldNoEncodeToPEM
+	}
+	signaturePart.SetContent(*pemMsg)
+
+	return nil
+}
+
+// createMessage prepares the message that will be used for the sign method later
+func (sm *SMime) createMessage(encoding Encoding, contentType ContentType, charset Charset, body []byte) string {
+	return fmt.Sprintf("Content-Transfer-Encoding: %v\r\nContent-Type: %v; charset=%v\r\n\r\n%v", encoding, contentType, charset, string(body))
+}
+
+// encodeToPEM uses the method pem.Encode from the standard library but cuts the typical PEM preamble
+func encodeToPEM(msg []byte) (*string, error) {
+	block := &pem.Block{Bytes: msg}
+
+	var arrayBuffer bytes.Buffer
+	if err := pem.Encode(&arrayBuffer, block); err != nil {
+		return nil, err
+	}
+
+	r := arrayBuffer.String()
+	r = strings.ReplaceAll(r, "-----BEGIN -----\n", "")
+	r = strings.ReplaceAll(r, "-----END -----\n", "")
+
+	return &r, nil
+}
+
+// line is the representation of one line of the message that will be used for signing purposes
+type line struct {
+	line      []byte
+	endOfLine []byte
+}
+
+// lines is the representation of a message that will be used for signing purposes
+type lines []line
+
+// bytesFromLines creates the line representation with the given endOfLine char
+func (ls lines) bytesFromLines(sep []byte) []byte {
+	var raw []byte
+	for i := range ls {
+		raw = append(raw, ls[i].line...)
+		if len(ls[i].endOfLine) != 0 && sep != nil {
+			raw = append(raw, sep...)
+		} else {
+			raw = append(raw, ls[i].endOfLine...)
+		}
+	}
+	return raw
+}
+
+// parseLines constructs the lines representation of a given message
+func parseLines(raw []byte) lines {
+	oneLine := line{raw, nil}
+	lines := lines{oneLine}
+	lines = lines.splitLine([]byte("\r\n"))
+	lines = lines.splitLine([]byte("\r"))
+	lines = lines.splitLine([]byte("\n"))
+	return lines
+}
+
+// splitLine uses the given endOfLine to split the given line
+func (ls lines) splitLine(sep []byte) lines {
+	nl := lines{}
+	for _, l := range ls {
+		split := bytes.Split(l.line, sep)
+		if len(split) > 1 {
+			for i := 0; i < len(split)-1; i++ {
+				nl = append(nl, line{split[i], sep})
+			}
+			nl = append(nl, line{split[len(split)-1], l.endOfLine})
+		} else {
+			nl = append(nl, l)
+		}
+	}
+	return nl
 }

util_test.go

@@ -1,41 +1,22 @@
 package mail
 
 import (
-	"crypto/rand"
-	"crypto/rsa"
+	"crypto/tls"
 	"crypto/x509"
-	"crypto/x509/pkix"
-	"math/big"
-	"time"
 )
 
-func getDummyPrivateKey() (*rsa.PrivateKey, error) {
-	privateKey, err := rsa.GenerateKey(rand.Reader, 2048)
-	if err != nil {
-		return nil, err
-	}
-	return privateKey, nil
-}
+const (
+	certFilePath = "dummy-chain-cert.pem"
+	keyFilePath  = "dummy-child-key.pem"
+)
 
-func getDummyCertificate(privateKey *rsa.PrivateKey) (*x509.Certificate, error) {
-	template := &x509.Certificate{
-		SerialNumber: big.NewInt(1234),
-		Subject:      pkix.Name{Organization: []string{"My Organization"}},
-		NotBefore:    time.Now(),
-		NotAfter:     time.Now().AddDate(1, 0, 0),
-		KeyUsage:     x509.KeyUsageDigitalSignature,
-		ExtKeyUsage:  []x509.ExtKeyUsage{x509.ExtKeyUsageServerAuth},
-	}
-
-	certDER, err := x509.CreateCertificate(rand.Reader, template, template, &privateKey.PublicKey, privateKey)
+func getDummyCertificate() (*tls.Certificate, error) {
+	keyPair, err := tls.LoadX509KeyPair(certFilePath, keyFilePath)
 	if err != nil {
 		return nil, err
 	}
 
-	cert, err := x509.ParseCertificate(certDER)
-	if err != nil {
-		return nil, err
-	}
+	keyPair.Leaf, err = x509.ParseCertificate(keyPair.Certificate[0])
 
-	return cert, nil
+	return &keyPair, nil
 }