Process 1 build 0203261953

backend/app/services/diagnostics.py

@@ -18,7 +18,7 @@ from ..clients.sonarr import SonarrClient
 from ..config import settings as env_settings
 from ..db import run_integrity_check
 from ..runtime import get_runtime_settings
-from .invite_email import send_test_email, smtp_email_config_ready
+from .invite_email import send_test_email, smtp_email_config_ready, smtp_email_delivery_warning
 
 
 DiagnosticRunner = Callable[[], Awaitable[Dict[str, Any]]]
@@ -302,6 +302,13 @@ async def _run_jellyfin_check(runtime) -> Dict[str, Any]:
 async def _run_email_check(recipient_email: Optional[str] = None) -> Dict[str, Any]:
     result = await send_test_email(recipient_email=recipient_email)
     recipient = _clean_text(result.get("recipient_email"), "configured recipient")
+    warning = _clean_text(result.get("warning"))
+    if warning:
+        return {
+            "status": "degraded",
+            "message": f"SMTP relay accepted a test for {recipient}, but delivery is not guaranteed.",
+            "detail": result,
+        }
     return {"message": f"Test email sent to {recipient}", "detail": result}
 
 
@@ -425,6 +432,7 @@ def _build_diagnostic_checks(recipient_email: Optional[str] = None) -> List[Diag
         push_target = _url_target(runtime.magent_notify_push_base_url)
 
     email_ready, email_detail = smtp_email_config_ready()
+    email_warning = smtp_email_delivery_warning()
     discord_ready, discord_detail = _discord_config_ready(runtime)
     telegram_ready, telegram_detail = _telegram_config_ready(runtime)
     push_ready, push_detail = _push_config_ready(runtime)
@@ -539,7 +547,7 @@ def _build_diagnostic_checks(recipient_email: Optional[str] = None) -> List[Diag
             description="Sends a live test email using the configured SMTP provider.",
             live_safe=False,
             configured=email_ready,
-            config_detail=email_detail,
+            config_detail=email_warning or email_detail,
             target=smtp_target,
             runner=lambda recipient_email=recipient_email: _run_email_check(recipient_email),
         ),

backend/app/services/invite_email.py

@@ -382,6 +382,20 @@ def smtp_email_config_ready() -> tuple[bool, str]:
     return True, "ok"
 
 
+def smtp_email_delivery_warning() -> Optional[str]:
+    runtime = get_runtime_settings()
+    host = _normalize_display_text(runtime.magent_notify_email_smtp_host).lower()
+    username = _normalize_display_text(runtime.magent_notify_email_smtp_username)
+    password = _normalize_display_text(runtime.magent_notify_email_smtp_password)
+    if host.endswith(".mail.protection.outlook.com") and not (username and password):
+        return (
+            "Unauthenticated Microsoft 365 relay mode is configured. SMTP acceptance does not "
+            "confirm mailbox delivery. For reliable delivery, use smtp.office365.com:587 with "
+            "SMTP credentials or configure a verified Exchange relay connector."
+        )
+    return None
+
+
 def _send_email_sync(*, recipient_email: str, subject: str, body_text: str, body_html: str) -> None:
     runtime = get_runtime_settings()
     host = _normalize_display_text(runtime.magent_notify_email_smtp_host)
@@ -392,6 +406,7 @@ def _send_email_sync(*, recipient_email: str, subject: str, body_text: str, body
     from_name = _normalize_display_text(runtime.magent_notify_email_from_name, env_settings.app_name)
     use_tls = bool(runtime.magent_notify_email_use_tls)
     use_ssl = bool(runtime.magent_notify_email_use_ssl)
+    delivery_warning = smtp_email_delivery_warning()
     if not host or not from_address:
         raise RuntimeError("SMTP email settings are incomplete.")
     logger.info(
@@ -405,6 +420,8 @@ def _send_email_sync(*, recipient_email: str, subject: str, body_text: str, body
         bool(username and password),
         subject,
     )
+    if delivery_warning:
+        logger.warning("smtp delivery warning host=%s detail=%s", host, delivery_warning)
 
     message = EmailMessage()
     message["Subject"] = subject
@@ -515,4 +532,8 @@ async def send_test_email(recipient_email: Optional[str] = None) -> Dict[str, st
         body_html=body_html,
     )
     logger.info("SMTP test email sent: recipient=%s", resolved_email)
-    return {"recipient_email": resolved_email, "subject": subject}
+    result = {"recipient_email": resolved_email, "subject": subject}
+    warning = smtp_email_delivery_warning()
+    if warning:
+        result["warning"] = warning
+    return result