diff --git a/backend/app/services/chat_webhook_service.py b/backend/app/services/chat_webhook_service.py
index 65d5acaf..99473a6b 100644
--- a/backend/app/services/chat_webhook_service.py
+++ b/backend/app/services/chat_webhook_service.py
@@ -19,10 +19,9 @@ import logging
 import re
 from datetime import datetime
 
-import requests
-
 from app import db
 from app.models.chat_webhook import ChatWebhookConnection
+from app.utils import safe_http
 from app.utils.crypto import encrypt_secret
 
 logger = logging.getLogger(__name__)
@@ -405,8 +404,11 @@ class ChatWebhookService:
             headers[SIGNATURE_HEADER] = 'sha256=' + signature
 
         try:
-            resp = requests.post(url, data=body, headers=headers,
-                                 timeout=_REQUEST_TIMEOUT)
+            resp = safe_http.post(url, data=body, headers=headers,
+                                  timeout=_REQUEST_TIMEOUT)
+        except safe_http.UnsafeURLError as exc:
+            # Non-retryable: the URL itself is the problem, retrying can't help.
+            return DeliveryResult.skipped(f'webhook url refused: {exc}')
         except Exception as exc:  # network error -> retryable failure
             return DeliveryResult.failed(str(exc))
 
diff --git a/backend/app/services/monitoring_service.py b/backend/app/services/monitoring_service.py
index cba6d702..ed8a576a 100644
--- a/backend/app/services/monitoring_service.py
+++ b/backend/app/services/monitoring_service.py
@@ -214,7 +214,7 @@ class MonitoringService:
     @classmethod
     def send_webhook_alert(cls, alerts: List[Dict]) -> Dict:
         """Send webhook alert notification."""
-        import requests
+        from app.utils import safe_http
 
         config = cls.get_config()
         webhook_config = config.get('webhook', {})
@@ -229,7 +229,7 @@ class MonitoringService:
                 'alerts': alerts
             }
 
-            response = requests.post(
+            response = safe_http.post(
                 webhook_config['url'],
                 json=payload,
                 timeout=10
@@ -239,6 +239,8 @@ class MonitoringService:
                 return {'success': True, 'message': 'Webhook sent'}
             return {'success': False, 'error': f'Webhook returned {response.status_code}'}
 
+        except safe_http.UnsafeURLError as e:
+            return {'success': False, 'error': f'Webhook URL refused: {e}'}
         except Exception as e:
             return {'success': False, 'error': str(e)}
 
diff --git a/backend/tests/test_notification_chat_connections.py b/backend/tests/test_notification_chat_connections.py
index 202b8b09..ec1f3df0 100644
--- a/backend/tests/test_notification_chat_connections.py
+++ b/backend/tests/test_notification_chat_connections.py
@@ -321,7 +321,7 @@ class TestSigningAndDelivery:
             captured.update({'url': url, 'data': data, 'headers': headers})
             return _Resp()
 
-        monkeypatch.setattr('app.services.chat_webhook_service.requests.post', fake_post)
+        monkeypatch.setattr('app.services.chat_webhook_service.safe_http.post', fake_post)
 
         user = _make_user()
         conn = ChatWebhookService.add({'kind': 'webhook', 'name': 'Ops', 'url': 'https://hooks/x',
@@ -392,7 +392,7 @@ class TestConnectionTesting:
             status_code = 503
 
         monkeypatch.setattr(
-            'app.services.chat_webhook_service.requests.post',
+            'app.services.chat_webhook_service.safe_http.post',
             lambda *args, **kwargs: _Resp(),
         )
         conn = ChatWebhookService.add({
@@ -428,7 +428,7 @@ class TestConnectionTesting:
             raise RuntimeError(f'failed POST {url}')
 
         monkeypatch.setattr(
-            'app.services.chat_webhook_service.requests.post', fail_post,
+            'app.services.chat_webhook_service.safe_http.post', fail_post,
         )
         secret_url = 'https://hooks.example/super-secret-token'
         conn = ChatWebhookService.add({
@@ -454,7 +454,7 @@ class TestConnectionTesting:
             raise RuntimeError(f'failed POST {url}')
 
         monkeypatch.setattr(
-            'app.services.chat_webhook_service.requests.post', fail_post,
+            'app.services.chat_webhook_service.safe_http.post', fail_post,
         )
         conn = ChatWebhookService.add({
             'kind': 'webhook',
@@ -624,7 +624,7 @@ class TestApi:
             status_code = 503
 
         monkeypatch.setattr(
-            'app.services.chat_webhook_service.requests.post',
+            'app.services.chat_webhook_service.safe_http.post',
             lambda *args, **kwargs: _Resp(),
         )
         conn = ChatWebhookService.add({
diff --git a/backend/tests/test_webhook_ssrf_guard.py b/backend/tests/test_webhook_ssrf_guard.py
new file mode 100644
index 00000000..e5482724
--- /dev/null
+++ b/backend/tests/test_webhook_ssrf_guard.py
@@ -0,0 +1,37 @@
+"""User-configured webhook URLs must go through app.utils.safe_http."""
+import pytest
+
+from app.notifications.channels.base import DeliveryResult
+from app.services.chat_webhook_service import ChatWebhookService
+from app.services.monitoring_service import MonitoringService
+
+PRIVATE_URLS = ['http://127.0.0.1:5000/hook', 'http://169.254.169.254/latest/meta-data', 'http://localhost/x']
+
+
+@pytest.mark.parametrize('url', PRIVATE_URLS)
+def test_monitoring_webhook_refuses_private_targets(url, monkeypatch):
+    monkeypatch.setattr(MonitoringService, 'get_config',
+                        classmethod(lambda cls: {'webhook': {'enabled': True, 'url': url}}))
+    result = MonitoringService.send_webhook_alert([{'type': 'cpu'}])
+    assert result['success'] is False
+    assert 'refused' in result['error']
+
+
+@pytest.mark.parametrize('url', PRIVATE_URLS)
+def test_chat_webhook_refuses_private_targets(url):
+    class _Notification:
+        severity = 'info'
+        event_key = 'x'
+        title = 't'
+        body = 'b'
+        created_at = None
+        category = 'c'
+        action_path = None
+        id = 1
+
+        def get_data(self):
+            return {}
+
+    result = ChatWebhookService._deliver_webhook(None, {'url': url}, _Notification())
+    assert result.status == DeliveryResult.SKIPPED  # terminal: the queue must not retry
+    assert 'refused' in result.error