diff --git a/engine/apps/alerts/escalation_snapshot/snapshot_classes/escalation_policy_snapshot.py b/engine/apps/alerts/escalation_snapshot/snapshot_classes/escalation_policy_snapshot.py
index 98d894a4..541b5ffb 100644
--- a/engine/apps/alerts/escalation_snapshot/snapshot_classes/escalation_policy_snapshot.py
+++ b/engine/apps/alerts/escalation_snapshot/snapshot_classes/escalation_policy_snapshot.py
@@ -472,24 +472,32 @@ class EscalationPolicySnapshot:
     def _escalation_step_trigger_custom_webhook(self, alert_group: "AlertGroup", _reason: str) -> None:
         tasks = []
         webhook = self.custom_webhook
+        failure_reason = None
         if webhook is not None:
-            custom_webhook_task = custom_webhook_result.signature(
-                (webhook.pk, alert_group.pk),
-                {
-                    "escalation_policy_pk": self.id,
-                },
-                immutable=True,
-            )
-            tasks.append(custom_webhook_task)
+            if webhook.is_webhook_enabled:
+                custom_webhook_task = custom_webhook_result.signature(
+                    (webhook.pk, alert_group.pk),
+                    {
+                        "escalation_policy_pk": self.id,
+                    },
+                    immutable=True,
+                )
+                tasks.append(custom_webhook_task)
+            else:
+                failure_reason = AlertGroupLogRecord.ERROR_ESCALATION_TRIGGER_WEBHOOK_IS_DISABLED
         else:
+            failure_reason = AlertGroupLogRecord.ERROR_ESCALATION_TRIGGER_WEBHOOK_STEP_IS_NOT_CONFIGURED
+
+        if failure_reason:
             log_record = AlertGroupLogRecord(
                 type=AlertGroupLogRecord.TYPE_ESCALATION_FAILED,
                 alert_group=alert_group,
                 escalation_policy=self.escalation_policy,
-                escalation_error_code=AlertGroupLogRecord.ERROR_ESCALATION_TRIGGER_WEBHOOK_STEP_IS_NOT_CONFIGURED,
+                escalation_error_code=failure_reason,
                 escalation_policy_step=self.step,
             )
             log_record.save()
+
         self._execute_tasks(tasks)
 
     def _escalation_step_repeat_escalation_n_times(
diff --git a/engine/apps/alerts/models/alert_group_log_record.py b/engine/apps/alerts/models/alert_group_log_record.py
index e76e41f5..7da4f247 100644
--- a/engine/apps/alerts/models/alert_group_log_record.py
+++ b/engine/apps/alerts/models/alert_group_log_record.py
@@ -160,7 +160,8 @@ class AlertGroupLogRecord(models.Model):
         ERROR_ESCALATION_NOTIFY_IF_NUM_ALERTS_IN_WINDOW_STEP_IS_NOT_CONFIGURED,
         ERROR_ESCALATION_TRIGGER_CUSTOM_WEBHOOK_ERROR,
         ERROR_ESCALATION_NOTIFY_TEAM_MEMBERS_STEP_IS_NOT_CONFIGURED,
-    ) = range(19)
+        ERROR_ESCALATION_TRIGGER_WEBHOOK_IS_DISABLED,
+    ) = range(20)
 
     type = models.IntegerField(choices=TYPE_CHOICES)
 
@@ -590,6 +591,8 @@ class AlertGroupLogRecord(models.Model):
                         usergroup_handle = self.escalation_policy.notify_to_group.handle
                     usergroup_handle_text = f" @{usergroup_handle}" if usergroup_handle else ""
                     result += f"failed to notify User Group{usergroup_handle_text} in Slack"
+            elif self.escalation_error_code == AlertGroupLogRecord.ERROR_ESCALATION_TRIGGER_WEBHOOK_IS_DISABLED:
+                result += 'skipped escalation step "Trigger Outgoing Webhook" because it is disabled'
         return result
 
     def get_step_specific_info(self):
diff --git a/engine/apps/alerts/tests/test_escalation_policy_snapshot.py b/engine/apps/alerts/tests/test_escalation_policy_snapshot.py
index b959fe73..8a3eef60 100644
--- a/engine/apps/alerts/tests/test_escalation_policy_snapshot.py
+++ b/engine/apps/alerts/tests/test_escalation_policy_snapshot.py
@@ -486,6 +486,33 @@ def test_escalation_step_trigger_custom_webhook(
         mock_webhook_escalation_step.assert_called_once_with(alert_group, reason)
 
 
+@patch("apps.alerts.escalation_snapshot.snapshot_classes.EscalationPolicySnapshot._execute_tasks", return_value=None)
+@pytest.mark.django_db
+def test_escalation_step_trigger_disabled_custom_webhook(
+    mocked_execute_tasks,
+    escalation_step_test_setup,
+    make_custom_webhook,
+    make_escalation_policy,
+):
+    organization, _, _, channel_filter, alert_group, reason = escalation_step_test_setup
+
+    custom_webhook = make_custom_webhook(organization=organization, is_webhook_enabled=False)
+
+    trigger_custom_webhook_step = make_escalation_policy(
+        escalation_chain=channel_filter.escalation_chain,
+        escalation_policy_step=EscalationPolicy.STEP_TRIGGER_CUSTOM_WEBHOOK,
+        custom_webhook=custom_webhook,
+    )
+    escalation_policy_snapshot = get_escalation_policy_snapshot_from_model(trigger_custom_webhook_step)
+    escalation_policy_snapshot.execute(alert_group, reason)
+    assert call([]) in mocked_execute_tasks.call_args_list
+
+    log_record = AlertGroupLogRecord.objects.get(
+        alert_group_id=alert_group.id, escalation_policy=trigger_custom_webhook_step
+    )
+    assert log_record.escalation_error_code == AlertGroupLogRecord.ERROR_ESCALATION_TRIGGER_WEBHOOK_IS_DISABLED
+
+
 @patch("apps.alerts.escalation_snapshot.snapshot_classes.EscalationPolicySnapshot._execute_tasks", return_value=None)
 @pytest.mark.django_db
 def test_escalation_step_repeat_escalation_n_times(