diff --git a/.github/workflows/close-stale-issues.yml b/.github/workflows/close-stale-issues.yml
index d5bcb05..8f09675 100644
--- a/.github/workflows/close-stale-issues.yml
+++ b/.github/workflows/close-stale-issues.yml
@@ -10,7 +10,7 @@ jobs:
       issues: write
       pull-requests: write
     steps:
-      - uses: actions/stale@v8.0.0
+      - uses: actions/stale@v9.0.0
         with:
           days-before-issue-stale: 21
           days-before-issue-close: 7
diff --git a/.github/workflows/codeql-analysis.yml b/.github/workflows/codeql-analysis.yml
index 60c92dd..847bbea 100644
--- a/.github/workflows/codeql-analysis.yml
+++ b/.github/workflows/codeql-analysis.yml
@@ -42,7 +42,7 @@ jobs:
 
     # Initializes the CodeQL tools for scanning.
     - name: Initialize CodeQL
-      uses: github/codeql-action/init@v2
+      uses: github/codeql-action/init@v3
       with:
         languages: ${{ matrix.language }}
         # If you wish to specify custom queries, you can do so here or in a config file.
@@ -56,7 +56,7 @@ 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@v2
+      uses: github/codeql-action/autobuild@v3
 
     # ℹ️ Command-line programs to run using the OS shell.
     # 📚 See https://docs.github.com/en/actions/using-workflows/workflow-syntax-for-github-actions#jobsjob_idstepsrun
@@ -69,4 +69,4 @@ jobs:
     #   ./location_of_script_within_repo/buildscript.sh
 
     - name: Perform CodeQL Analysis
-      uses: github/codeql-action/analyze@v2
+      uses: github/codeql-action/analyze@v3
diff --git a/.github/workflows/release-build.yml b/.github/workflows/release-build.yml
index 112e92b..c9a9a6e 100644
--- a/.github/workflows/release-build.yml
+++ b/.github/workflows/release-build.yml
@@ -21,7 +21,7 @@ jobs:
     - uses: actions/checkout@v4
 
     # build the binaries
-    - uses: wangyoucao577/go-release-action@v1.40
+    - uses: wangyoucao577/go-release-action@v1.51
       with:
         github_token: ${{ secrets.GITHUB_TOKEN }}
         goos: ${{ matrix.goos }}
diff --git a/cmd/mailer.go b/cmd/mailer.go
index e1d3385..ee2c679 100644
--- a/cmd/mailer.go
+++ b/cmd/mailer.go
@@ -1,17 +1,27 @@
 package cmd
 
 import (
+	"bytes"
 	"crypto/tls"
 	"fmt"
-	"io"
+	"net/mail"
 	"net/smtp"
 	"os"
+	"regexp"
+	"strconv"
 	"strings"
 	"time"
+
+	"github.com/lithammer/shortuuid"
 )
 
 // SMTP wrapper will send and optionally log the transaction
-func smtpWrapper(from string, to []string, msg []byte) error {
+func smtpWrapper(from string, to []string, message []byte) error {
+	msg, err := injectHeaders(message)
+	if err != nil {
+		return err
+	}
+
 	code, response, err := smtpSend(from, to, msg)
 
 	if config.LogFile != "" {
@@ -21,11 +31,15 @@ func smtpWrapper(from string, to []string, msg []byte) error {
 		if config.STARTTLS {
 			tls = "on"
 		}
+		if err != nil {
+			code, response = smtpErrParser(err.Error())
+		}
+
 		recipients := strings.Join(to, ",")
 		logMsg := fmt.Sprintf("%s host=%s tls=%s from=%s, recipients=%s mailsize=%d, smtpstatus=%d smtpmsg='%s'\n", ts, config.SMTPHost, tls, from, recipients, len(msg), code, response)
 
 		file, err := os.OpenFile(config.LogFile, os.O_CREATE|os.O_APPEND|os.O_WRONLY, 0666) // #nosec
-		// silently fail if the file cannot be opened
+		// silently fail if the log file cannot be opened
 		if err == nil {
 			defer file.Close()
 			_, _ = file.Write([]byte(logMsg))
@@ -75,6 +89,7 @@ func smtpSend(from string, to []string, msg []byte) (int, string, error) {
 			return 0, "", err
 		}
 	}
+
 	if err = c.Mail(from); err != nil {
 		return 0, "", err
 	}
@@ -85,41 +100,79 @@ func smtpSend(from string, to []string, msg []byte) (int, string, error) {
 		}
 	}
 
-	w, err := c.Data()
+	code, message, err := dataWithResponse(c, msg)
 	if err != nil {
 		return 0, "", err
 	}
 
-	if _, err := w.Write(msg); err != nil {
+	return code, message, c.Quit()
+}
+
+// Go's net/smtp Data() only returns an error message. This custom function
+// also returns the server's response message so it can be logged.
+//
+// @see https://github.com/axllent/sndmail/issues/10#issuecomment-2214807859
+func dataWithResponse(c *smtp.Client, msg []byte) (int, string, error) {
+	id, err := c.Text.Cmd("DATA")
+	if err != nil {
 		return 0, "", err
 	}
 
-	defer c.Quit()
+	c.Text.StartResponse(id)
 
-	code, message, err := closeData(c)
+	code, message, err := c.Text.ReadResponse(354)
+	if err != nil {
+		return code, message, err
+	}
 
-	return code, message, err
-}
+	c.Text.EndResponse(id)
+
+	w := c.Text.DotWriter()
 
-// CloseData wil ensure the SMTP server response is returned
-// @see https://stackoverflow.com/a/70925659
-func closeData(client *smtp.Client) (int, string, error) {
-	d := &dataCloser{
-		c:           client,
-		WriteCloser: client.Text.DotWriter(),
+	if _, err := w.Write(msg); err != nil {
+		return 0, "", err
+	}
+
+	if err := w.Close(); err != nil {
+		return 0, "", err
 	}
 
-	return d.Close()
+	return c.Text.ReadResponse(250)
 }
 
-type dataCloser struct {
-	c *smtp.Client
-	io.WriteCloser
+// Inject Message-Id and Date if missing
+func injectHeaders(body []byte) ([]byte, error) {
+	msg, err := mail.ReadMessage(bytes.NewReader(body))
+	if err != nil {
+		return nil, err
+	}
+
+	// add message ID if missing
+	if msg.Header.Get("Message-Id") == "" {
+		messageID := shortuuid.New() + "@sndmail"
+		body = append([]byte("Message-Id: <"+messageID+">\r\n"), body...)
+	}
+
+	// add date if missing
+	if msg.Header.Get("Date") == "" {
+		now := time.Now().Format("Mon, 02 Jan 2006 15:04:05 -0700 (MST)")
+		body = append([]byte("Date: "+now+"\r\n"), body...)
+	}
+
+	return body, nil
 }
 
-func (d *dataCloser) Close() (int, string, error) {
-	d.WriteCloser.Close() // #nosec make sure WriterCloser gets closed
-	code, message, err := d.c.Text.ReadResponse(250)
+// error parser for SMTP response messages
+func smtpErrParser(s string) (int, string) {
+	var re = regexp.MustCompile(`(\d\d\d) (.*)`)
+	if re.MatchString(s) {
+		matches := re.FindAllStringSubmatch(s, -1)
+		for _, m := range matches {
+			i, _ := strconv.Atoi(m[1])
+
+			return i, m[2]
+		}
+	}
 
-	return code, message, err
+	return 0, s
 }
diff --git a/cmd/main.go b/cmd/main.go
index 839b7ec..d6b8656 100644
--- a/cmd/main.go
+++ b/cmd/main.go
@@ -32,7 +32,3 @@ func Exec() {
 		sendmail()
 	}
 }
-
-// func main() {
-// 	Cmd()
-// }
diff --git a/cmd/sendmail.go b/cmd/sendmail.go
index b45b497..31addef 100644
--- a/cmd/sendmail.go
+++ b/cmd/sendmail.go
@@ -27,7 +27,7 @@ func sendmail() {
 
 	msg, err := mail.ReadMessage(bytes.NewReader(body))
 	if err != nil {
-		// create blank message to lookups don't fail
+		// create blank message so lookups don't fail
 		msg = &mail.Message{}
 
 		// inject a new blank line below body
diff --git a/go.mod b/go.mod
index 9078384..df4922c 100644
--- a/go.mod
+++ b/go.mod
@@ -2,4 +2,9 @@ module github.com/axllent/sndmail
 
 go 1.19
 
-require github.com/spf13/pflag v1.0.5
+require (
+	github.com/lithammer/shortuuid v3.0.0+incompatible
+	github.com/spf13/pflag v1.0.5
+)
+
+require github.com/google/uuid v1.6.0 // indirect
diff --git a/go.sum b/go.sum
index 287f6fa..e73f3c8 100644
--- a/go.sum
+++ b/go.sum
@@ -1,2 +1,6 @@
+github.com/google/uuid v1.6.0 h1:NIvaJDMOsjHA8n1jAhLSgzrAzy1Hgr+hNrb57e+94F0=
+github.com/google/uuid v1.6.0/go.mod h1:TIyPZe4MgqvfeYDBFedMoGGpEw/LqOeaOT+nhxU+yHo=
+github.com/lithammer/shortuuid v3.0.0+incompatible h1:NcD0xWW/MZYXEHa6ITy6kaXN5nwm/V115vj2YXfhS0w=
+github.com/lithammer/shortuuid v3.0.0+incompatible/go.mod h1:FR74pbAuElzOUuenUHTK2Tciko1/vKuIKS9dSkDrA4w=
 github.com/spf13/pflag v1.0.5 h1:iy+VFUOCP1a+8yFto/drg2CJ5u0yRoB7fZw3DKv/JXA=
 github.com/spf13/pflag v1.0.5/go.mod h1:McXfInJRrz4CZXVZOBLb0bTZqETkiAhM9Iw0y3An2Bg=