diff --git a/puppy_kit/commands/incident.py b/puppy_kit/commands/incident.py
index 6c82f97..b567b9b 100644
--- a/puppy_kit/commands/incident.py
+++ b/puppy_kit/commands/incident.py
@@ -597,6 +597,12 @@ def create_incident(title, description, severity, team, assignee, customer_impac
     type=click.Choice(["yes", "no"]),
     help="Is duplicate flag",
 )
+@click.option(
+    "--needs-wrench-bot-check",
+    default=None,
+    type=click.Choice(["yes", "no"]),
+    help="NeedsWrenchBotCheck flag — set to yes to trigger the triage webhook",
+)
 @click.option("--teams", multiple=True, default=None, help="Team names (repeatable)")
 @click.option("--services", multiple=True, default=None, help="Service names (repeatable)")
 @click.option(
@@ -621,6 +627,7 @@ def update_incident(
     needs_human_attention,
     triage_completed,
     is_duplicate,
+    needs_wrench_bot_check,
     teams,
     services,
     related_incidents,
@@ -648,6 +655,7 @@ def update_incident(
         needs_human_attention,
         triage_completed,
         is_duplicate,
+        needs_wrench_bot_check,
         teams,
         services,
         related_incidents,
@@ -719,6 +727,11 @@ def update_incident(
             "type": "dropdown",
             "value": is_duplicate.capitalize(),
         }
+    if needs_wrench_bot_check is not None:
+        field_data["NeedsWrenchBotCheck"] = {
+            "type": "dropdown",
+            "value": needs_wrench_bot_check.capitalize(),
+        }
     if teams:
         field_data["teams"] = {"type": "autocomplete", "value": list(teams)}
     if services:
diff --git a/tests/commands/test_incident.py b/tests/commands/test_incident.py
index 42531e1..f57e2a8 100644
--- a/tests/commands/test_incident.py
+++ b/tests/commands/test_incident.py
@@ -434,6 +434,28 @@ def test_update_incident_assignee(self, mock_client, runner):
         assert "muhammad" in result.output
         mock_client.incidents.update_incident.assert_called_once()
 
+    def test_update_incident_needs_wrench_bot_check(self, mock_client, runner):
+        """Test that --needs-wrench-bot-check sets NeedsWrenchBotCheck in field_data."""
+        inc = _make_incident("inc-1", "Service outage", "SEV-3", "active")
+        response = Mock(data=inc)
+        mock_client.incidents.update_incident.return_value = response
+
+        mock_cfg = Mock(site="datadoghq.com", api_key="test-api-key", app_key="test-app-key")
+        with patch("puppy_kit.commands.incident.get_datadog_client", return_value=mock_client):
+            with patch("puppy_kit.commands.incident.load_config", return_value=mock_cfg):
+                with patch("puppy_kit.commands.incident.requests.patch") as mock_patch:
+                    mock_patch.return_value = Mock(raise_for_status=Mock())
+                    result = runner.invoke(
+                        incident,
+                        ["update", "inc-1", "--needs-wrench-bot-check", "yes"],
+                    )
+
+        assert result.exit_code == 0, f"Command failed: {result.output}"
+        assert "updated" in result.output
+        _, kwargs = mock_patch.call_args
+        sent_fields = kwargs["json"]["data"]["attributes"]["fields"]
+        assert sent_fields["NeedsWrenchBotCheck"] == {"type": "dropdown", "value": "Yes"}
+
 
 class TestSetStatusIncident:
     def test_set_status_table(self, runner):