diff --git a/cueapi/cli.py b/cueapi/cli.py
index 794f0be..c036310 100644
--- a/cueapi/cli.py
+++ b/cueapi/cli.py
@@ -1662,7 +1662,11 @@ def agents_webhook_secret_regenerate(ctx: click.Context, ref: str, yes: bool) ->
             return
     try:
         with CueAPIClient(api_key=ctx.obj.get("api_key"), profile=ctx.obj.get("profile")) as client:
-            resp = client.post(f"/agents/{ref}/webhook-secret/regenerate", json={})
+            resp = client.post(
+                f"/agents/{ref}/webhook-secret/regenerate",
+                json={},
+                headers={"X-Confirm-Destructive": "true"},
+            )
             if resp.status_code == 200:
                 data = resp.json()
                 click.echo()
diff --git a/tests/test_cli.py b/tests/test_cli.py
index 4e8c37c..314a299 100644
--- a/tests/test_cli.py
+++ b/tests/test_cli.py
@@ -682,6 +682,34 @@ def test_agents_webhook_secret_regenerate_with_yes(monkeypatch):
     assert "save now" in result.output.lower() or "shown once" in result.output.lower()
 
 
+def test_agents_webhook_secret_regenerate_sends_destructive_header(monkeypatch):
+    """Pin: `cueapi agents webhook-secret regenerate` MUST send
+    `X-Confirm-Destructive: true` header — server requires it (Bug
+    cmp03hy9o, surfaced 2026-05-10 from Phase 2 messaging smoke).
+    Mirrors the same header pin on `cueapi key webhook-secret regenerate`.
+    """
+    holder: dict = {}
+    _patch_ws_client(
+        monkeypatch,
+        holder,
+        responses={
+            ("POST", "/agents/agt_x/webhook-secret/regenerate"): lambda: _FakeResp(
+                200, {"webhook_secret": "wsec_new"}
+            )
+        },
+    )
+    result = runner.invoke(
+        main,
+        ["agents", "webhook-secret", "regenerate", "agt_x", "--yes"],
+    )
+    assert result.exit_code == 0, result.output
+    method, path, body, headers = holder["client"].calls[-1]
+    assert method == "POST"
+    assert path == "/agents/agt_x/webhook-secret/regenerate"
+    assert headers == {"X-Confirm-Destructive": "true"}
+    assert "wsec_new" in result.output
+
+
 # --- inbox / sent ---