diff --git a/app/core/jobs.py b/app/core/jobs.py
index aca10c4..717bd36 100644
--- a/app/core/jobs.py
+++ b/app/core/jobs.py
@@ -133,14 +133,17 @@ async def send_password_reset_email(
     msg.attach(MIMEText(text_body, "plain", "utf-8"))
     msg.attach(MIMEText(html_body, "html", "utf-8"))
 
-    # Send via SMTP
+    # Send via SMTP (port 465 = implicit TLS, port 587 = STARTTLS)
+    use_tls = settings.smtp_port == 465
+    start_tls = settings.smtp_use_tls and not use_tls
     await aiosmtplib.send(
         msg,
         hostname=settings.smtp_host,
         port=settings.smtp_port,
         username=settings.smtp_username,
         password=settings.smtp_password,
-        start_tls=settings.smtp_use_tls,
+        use_tls=use_tls,
+        start_tls=start_tls,
     )
     logger.info("Password reset email sent to %s for user %s", email, user_id)