diff --git a/backend/app/api/notifications.py b/backend/app/api/notifications.py
index 36ef944..4a82963 100644
--- a/backend/app/api/notifications.py
+++ b/backend/app/api/notifications.py
@@ -216,8 +216,13 @@ async def test_email(
         msg["From"] = from_addr
         msg["To"] = email_addr
 
-        with smtplib.SMTP(app_settings.SMTP_HOST, app_settings.SMTP_PORT, timeout=10) as s:
-            if app_settings.SMTP_STARTTLS:
+        use_ssl = app_settings.SMTP_PORT == 465
+        if use_ssl:
+            ctx = smtplib.SMTP_SSL(app_settings.SMTP_HOST, app_settings.SMTP_PORT, timeout=10)
+        else:
+            ctx = smtplib.SMTP(app_settings.SMTP_HOST, app_settings.SMTP_PORT, timeout=10)
+        with ctx as s:
+            if not use_ssl and app_settings.SMTP_STARTTLS:
                 s.starttls()
             if app_settings.SMTP_USER:
                 s.login(app_settings.SMTP_USER, app_settings.SMTP_PASSWORD)
diff --git a/backend/app/workers/notification_dispatcher.py b/backend/app/workers/notification_dispatcher.py
index 5209dcd..de9d7dc 100644
--- a/backend/app/workers/notification_dispatcher.py
+++ b/backend/app/workers/notification_dispatcher.py
@@ -339,8 +339,13 @@ def _send_email(
         msg["List-Unsubscribe-Post"] = "List-Unsubscribe=One-Click"
     msg.attach(MIMEText(body, "plain", "utf-8"))
 
-    with smtplib.SMTP(app_settings.SMTP_HOST, app_settings.SMTP_PORT, timeout=10) as s:
-        if app_settings.SMTP_STARTTLS:
+    use_ssl = app_settings.SMTP_PORT == 465
+    if use_ssl:
+        smtp_ctx = smtplib.SMTP_SSL(app_settings.SMTP_HOST, app_settings.SMTP_PORT, timeout=10)
+    else:
+        smtp_ctx = smtplib.SMTP(app_settings.SMTP_HOST, app_settings.SMTP_PORT, timeout=10)
+    with smtp_ctx as s:
+        if not use_ssl and app_settings.SMTP_STARTTLS:
             s.starttls()
         if app_settings.SMTP_USER:
             s.login(app_settings.SMTP_USER, app_settings.SMTP_PASSWORD)