From f8e3b34a8a38367857567dcc5cde0724f55fc9fc Mon Sep 17 00:00:00 2001
From: "Rodrigo Rodriguez (Pragmatismo)" <me@rodrigorodriguez.com>
Date: Sat, 4 Apr 2026 20:25:59 -0300
Subject: [PATCH] fix: use builder_dangerous for port 25 (local Stalwart),
 starttls_relay for 465/587

---
 src/email/types.rs | 24 ++++++++++++++++--------
 1 file changed, 16 insertions(+), 8 deletions(-)

diff --git a/src/email/types.rs b/src/email/types.rs
index 6161f02c..a42fc047 100644
--- a/src/email/types.rs
+++ b/src/email/types.rs
@@ -353,16 +353,20 @@ impl EmailService {
             .body(body.to_string())
             .map_err(|e| format!("Failed to build email: {}", e))?;
 
-        let mailer = if !smtp_user.is_empty() && !smtp_pass.is_empty() {
+        let mailer = if smtp_port == 465 {
+            SmtpTransport::starttls_relay(&smtp_host)
+                .map_err(|e| format!("SMTP relay error: {}", e))?
+                .port(smtp_port)
+                .build()
+        } else if !smtp_user.is_empty() && !smtp_pass.is_empty() {
             let creds = Credentials::new(smtp_user, smtp_pass);
-            SmtpTransport::relay(&smtp_host)
+            SmtpTransport::starttls_relay(&smtp_host)
                 .map_err(|e| format!("SMTP relay error: {}", e))?
                 .port(smtp_port)
                 .credentials(creds)
                 .build()
         } else {
-            SmtpTransport::relay(&smtp_host)
-                .map_err(|e| format!("SMTP relay error: {}", e))?
+            SmtpTransport::builder_dangerous(&smtp_host)
                 .port(smtp_port)
                 .build()
         };
@@ -439,16 +443,20 @@ impl EmailService {
             )
             .map_err(|e| format!("Failed to build email: {}", e))?;
 
-        let mailer = if !smtp_user.is_empty() && !smtp_pass.is_empty() {
+        let mailer = if smtp_port == 465 {
+            SmtpTransport::starttls_relay(&smtp_host)
+                .map_err(|e| format!("SMTP relay error: {}", e))?
+                .port(smtp_port)
+                .build()
+        } else if !smtp_user.is_empty() && !smtp_pass.is_empty() {
             let creds = Credentials::new(smtp_user, smtp_pass);
-            SmtpTransport::relay(&smtp_host)
+            SmtpTransport::starttls_relay(&smtp_host)
                 .map_err(|e| format!("SMTP relay error: {}", e))?
                 .port(smtp_port)
                 .credentials(creds)
                 .build()
         } else {
-            SmtpTransport::relay(&smtp_host)
-                .map_err(|e| format!("SMTP relay error: {}", e))?
+            SmtpTransport::builder_dangerous(&smtp_host)
                 .port(smtp_port)
                 .build()
         };