diff --git a/backend/app/models.py b/backend/app/models.py
index 425ef59..efd9400 100644
--- a/backend/app/models.py
+++ b/backend/app/models.py
@@ -14,9 +14,6 @@ class User(Base):
     password_hash: Mapped[str] = mapped_column(String(255), nullable=False)
     role: Mapped[str] = mapped_column(String(20), nullable=False)
     is_active: Mapped[bool] = mapped_column(Boolean, nullable=False, default=True)
-    alert_delivery_status: Mapped[str | None] = mapped_column(String(30), nullable=True)
-    alert_delivered_at: Mapped[datetime | None] = mapped_column(DateTime, nullable=True)
-    alert_error_message: Mapped[str | None] = mapped_column(Text, nullable=True)
     created_at: Mapped[datetime] = mapped_column(DateTime, default=datetime.utcnow)
     updated_at: Mapped[datetime] = mapped_column(DateTime, default=datetime.utcnow, onupdate=datetime.utcnow)
     last_login_at: Mapped[datetime | None] = mapped_column(DateTime, nullable=True)
@@ -124,4 +121,7 @@ class WatchRun(Base):
     status: Mapped[str] = mapped_column(String(20), nullable=False)
     changed: Mapped[bool] = mapped_column(Boolean, nullable=False, default=False)
     summary: Mapped[str] = mapped_column(Text, nullable=False)
+    alert_delivery_status: Mapped[str | None] = mapped_column(String(30), nullable=True)
+    alert_delivered_at: Mapped[datetime | None] = mapped_column(DateTime, nullable=True)
+    alert_error_message: Mapped[str | None] = mapped_column(Text, nullable=True)
     created_at: Mapped[datetime] = mapped_column(DateTime, default=datetime.utcnow)
diff --git a/backend/app/services/alerting.py b/backend/app/services/alerting.py
index 3fd4dd7..728edd7 100644
--- a/backend/app/services/alerting.py
+++ b/backend/app/services/alerting.py
@@ -1,9 +1,20 @@
-import httpx
-import hmac, hashlib, json
 from datetime import datetime, timezone
+import hashlib
+import hmac
+import json
+
+import httpx
+
 from app.config import settings
 
-def send_watch_webhook(payload: dict) -> tuple[str,str|None]:
+
+MAX_ALERT_ERROR_MESSAGE_LENGTH = 500
+
+def _trim_error_message(exc: Exception) -> str:
+    return str(exc).strip()[:MAX_ALERT_ERROR_MESSAGE_LENGTH]
+
+
+def send_watch_webhook(payload: dict) -> tuple[str, str | None]:
     if not settings.alert_webhook_enabled:
         return 'skipped_disabled', None
     if not settings.alert_webhook_url:
@@ -14,8 +25,18 @@ def send_watch_webhook(payload: dict) -> tuple[str,str|None]:
     if settings.alert_webhook_secret:
         sig=hmac.new(settings.alert_webhook_secret.encode(), f"{ts}.{body}".encode(), hashlib.sha256).hexdigest()
         headers['X-RouteForge-Signature']=f'sha256={sig}'
-    try:
-        httpx.post(settings.alert_webhook_url,data=body,headers={**headers,'Content-Type':'application/json'},timeout=settings.alert_webhook_timeout_seconds)
-        return 'sent', None
-    except Exception as exc:
-        return 'failed', str(exc)
+    last_error: Exception | None = None
+    attempts = max(1, settings.alert_webhook_max_retries + 1)
+    for _ in range(attempts):
+        try:
+            response = httpx.post(
+                settings.alert_webhook_url,
+                data=body,
+                headers={**headers, 'Content-Type': 'application/json'},
+                timeout=settings.alert_webhook_timeout_seconds,
+            )
+            response.raise_for_status()
+            return 'sent', None
+        except Exception as exc:
+            last_error = exc
+    return 'failed', _trim_error_message(last_error) if last_error else 'webhook delivery failed'