redesign

backend/tests/test_mailer.py

@@ -103,7 +103,7 @@ class MailerTests(unittest.TestCase):
         self.assertEqual(result["attempts"][1]["status"], "ok")
         fallback_smtp.send_message.assert_called_once()
 
-    def test_send_email_message_rejects_unauthorized_from_address(self) -> None:
+    def test_send_email_message_retries_with_smtp_username_when_from_is_rejected(self) -> None:
         settings = SimpleNamespace(
             smtp_host="smtp.example.com",
             smtp_port=587,
@@ -116,25 +116,30 @@ class MailerTests(unittest.TestCase):
             smtp_timeout=15,
         )
         smtp = MagicMock()
-        smtp.send_message.side_effect = smtplib.SMTPDataError(
-            551, b"5.7.1 Not authorised to send from this header address"
-        )
+        smtp.send_message.side_effect = [
+            smtplib.SMTPDataError(551, b"5.7.1 Not authorised to send from this header address"),
+            {},
+        ]
         smtp_factory = MagicMock(return_value=_SMTPContext(smtp))
 
         with patch("media_library_viewer_api.services.mailer.smtplib.SMTP", smtp_factory), patch(
             "media_library_viewer_api.services.mailer.smtplib.SMTP_SSL"
         ) as smtp_ssl:
-            with self.assertRaises(RuntimeError) as ctx:
-                send_email_message(
-                    settings,
-                    recipients=["alex@example.com"],
-                    subject="Hello",
-                    html_body="<p>Hello</p>",
-                )
+            result = send_email_message(
+                settings,
+                recipients=["alex@example.com"],
+                subject="Hello",
+                html_body="<p>Hello</p>",
+            )
 
         smtp_ssl.assert_not_called()
-        self.assertIn("authorized alias", str(ctx.exception).lower())
-        self.assertEqual(smtp.send_message.call_count, 1)
+        self.assertEqual(result["from_address"], "mailer@example.com")
+        self.assertEqual(smtp.send_message.call_count, 2)
+        first_message = smtp.send_message.call_args_list[0].args[0]
+        second_message = smtp.send_message.call_args_list[1].args[0]
+        self.assertEqual(first_message["From"], "Manage <alias@example.com>")
+        self.assertEqual(second_message["From"], "Manage <mailer@example.com>")
+        self.assertEqual(second_message["Reply-To"], "alias@example.com")
 
     def test_describe_smtp_error_handles_timeout(self) -> None:
         detail = describe_smtp_error(TimeoutError("timed out"))