From 21e6ff3e9e5be6d99984e84f8cdacaa07a5dadfc Mon Sep 17 00:00:00 2001
From: Joe Julian <me@joejulian.name>
Date: Sat, 28 Mar 2026 16:35:34 -0700
Subject: [PATCH] Fix SMTP submission HELO handling

---
 README.md    |  1 +
 main.go      | 30 ++++++++++++++++++++++++++++++
 main_test.go |  9 +++++++++
 3 files changed, 40 insertions(+)

diff --git a/README.md b/README.md
index b75d09a..aeb0ea3 100644
--- a/README.md
+++ b/README.md
@@ -21,6 +21,7 @@ Recommended settings:
 - `ALMA_PASSWORD`
 - `SMTP_PORT=587`
 - `SMTP_STARTTLS=true`
+- `SMTP_HELO_NAME=mailer.example.invalid`
 - `SMTP_USERNAME`
 - `SMTP_PASSWORD`
 - `PRINT_REPORT=true`
diff --git a/main.go b/main.go
index f6c0de2..dc08098 100644
--- a/main.go
+++ b/main.go
@@ -39,6 +39,7 @@ type Config struct {
 	SMTPUsername   string
 	SMTPPassword   string
 	SMTPStartTLS   bool
+	SMTPHeloName   string
 	EmailFrom      string
 	EmailTo        []string
 	PrintReport    bool
@@ -172,6 +173,10 @@ func loadConfig() (Config, error) {
 		return Config{}, err
 	}
 	smtpStartTLS := readBool("SMTP_STARTTLS", true)
+	smtpHeloName, err := readValue("SMTP_HELO_NAME", "", false)
+	if err != nil {
+		return Config{}, err
+	}
 	emailFrom, err := readValue("EMAIL_FROM", "", false)
 	if err != nil {
 		return Config{}, err
@@ -204,6 +209,7 @@ func loadConfig() (Config, error) {
 		SMTPUsername:   smtpUsername,
 		SMTPPassword:   smtpPassword,
 		SMTPStartTLS:   smtpStartTLS,
+		SMTPHeloName:   normalizeSMTPHeloName(smtpHeloName),
 		EmailFrom:      emailFrom,
 		EmailTo:        emailTo,
 		PrintReport:    printReport,
@@ -594,11 +600,18 @@ func sendEmail(cfg Config, subject, body string) error {
 	defer conn.Close()
 
 	host := cfg.SMTPHost
+	heloName := normalizeSMTPHeloName(cfg.SMTPHeloName)
+	if err := conn.Hello(heloName); err != nil {
+		return err
+	}
 	if cfg.SMTPStartTLS {
 		if ok, _ := conn.Extension("STARTTLS"); ok {
 			if err := conn.StartTLS(&tls.Config{ServerName: host, MinVersion: tls.VersionTLS12}); err != nil {
 				return err
 			}
+			if err := conn.Hello(heloName); err != nil {
+				return err
+			}
 		}
 	}
 	if cfg.SMTPUsername != "" {
@@ -641,6 +654,23 @@ func sendEmail(cfg Config, subject, body string) error {
 	return conn.Quit()
 }
 
+func normalizeSMTPHeloName(value string) string {
+	value = strings.TrimSpace(value)
+	if value == "" {
+		hostname, err := os.Hostname()
+		if err == nil {
+			value = strings.TrimSpace(hostname)
+		}
+	}
+	if value == "" {
+		return "localhost.localdomain"
+	}
+	if strings.Contains(value, ".") {
+		return value
+	}
+	return value + ".localdomain"
+}
+
 func inferAssignmentDate(monthDay string, now time.Time) time.Time {
 	return inferDate(monthDay, now, false)
 }
diff --git a/main_test.go b/main_test.go
index 9f3589c..50088c2 100644
--- a/main_test.go
+++ b/main_test.go
@@ -132,6 +132,15 @@ func TestLoadAlmaCredsFromFile(t *testing.T) {
 	}
 }
 
+func TestNormalizeSMTPHeloName(t *testing.T) {
+	if got := normalizeSMTPHeloName("mail.example.invalid"); got != "mail.example.invalid" {
+		t.Fatalf("got %q", got)
+	}
+	if got := normalizeSMTPHeloName("mailer"); got != "mailer.localdomain" {
+		t.Fatalf("got %q", got)
+	}
+}
+
 func mustParseHTML(text string) *html.Node {
 	doc, err := html.Parse(strings.NewReader(text))
 	if err != nil {