From 80660982427349b473acdbf96b9c01c5cae8628a Mon Sep 17 00:00:00 2001
From: Richard Bergsma <richard@365devnet.eu>
Date: Sat, 7 Jun 2025 02:04:38 +0200
Subject: [PATCH] Update email handler to improve from address handling and
 enhance error logging

- Modify the from address logic to use a default 'noreply' address if SMTP_USER is not set in production.
- Add debug logging for email sending details, including connection target and sender/recipient information.
- Simplify error logging by removing specific SMTP error messages while retaining the full error stack for troubleshooting.
---
 src/utils/email-handler.ts | 29 ++++++-----------------------
 1 file changed, 6 insertions(+), 23 deletions(-)

diff --git a/src/utils/email-handler.ts b/src/utils/email-handler.ts
index a600d16..69e1246 100644
--- a/src/utils/email-handler.ts
+++ b/src/utils/email-handler.ts
@@ -170,8 +170,7 @@ export async function sendEmail(to: string, subject: string, html: string, text:
   }
 
   try {
-    // Ensure from address matches SMTP_USER for ProtonMail
-    const fromAddress = isProduction ? `"${WEBSITE_NAME}" <${SMTP_USER}>` : `"${WEBSITE_NAME}" <${ADMIN_EMAIL}>`;
+    const fromAddress = isProduction ? `"${WEBSITE_NAME}" <${SMTP_USER || 'noreply@' + WEBSITE_NAME}>` : `"${WEBSITE_NAME}" <${ADMIN_EMAIL}>`;
 
     const mailOptions = {
       from: fromAddress,
@@ -181,33 +180,17 @@ export async function sendEmail(to: string, subject: string, html: string, text:
       text,
     };
 
+    // Log the connection target
+    console.log(`[MAILER DEBUG] Sending via: ${SMTP_HOST}:${SMTP_PORT}`);
+    console.log(`[MAILER DEBUG] From: ${fromAddress} → To: ${to}`);
+
     await transporter.sendMail(mailOptions);
 
     logEmailAttempt(true, to, subject);
     return true;
   } catch (error) {
     logEmailAttempt(false, to, subject, error as Error);
-
-    // Enhanced error logging for SMTP issues
-    if (isProduction) {
-      console.error('Error sending email:', error);
-
-      // Log more detailed information for SMTP errors
-      if (error instanceof Error) {
-        console.error('Error name:', error.name);
-        console.error('Error message:', error.message);
-
-        // Log additional details for specific error types
-        if (error.name === 'Error' && error.message.includes('ECONNREFUSED')) {
-          console.error('SMTP Connection Refused: Check if the SMTP server is reachable and the port is correct');
-        } else if (error.message.includes('Invalid login')) {
-          console.error('SMTP Authentication Failed: Check your username and password');
-        } else if (error.message.includes('certificate')) {
-          console.error('SSL/TLS Certificate Error: There might be an issue with the server certificate');
-        }
-      }
-    }
-
+    console.error('Full SMTP error stack:', error);
     return false;
   }
 }