diff --git a/hermes_cli/urllib_security.py b/hermes_cli/urllib_security.py
index ae4ab8aff87..29c000985ae 100644
--- a/hermes_cli/urllib_security.py
+++ b/hermes_cli/urllib_security.py
@@ -64,7 +64,10 @@ class _CrossOriginRequestSanitizer(urllib.request.BaseHandler):
     # Request processors run in ascending order. Keep this last so an installed
     # cookie/auth/instrumentation processor cannot re-add a secret after the
     # redirect handler sanitizes the new Request.
-    handler_order = 1_000_000_000
+    # Infinity is greater than every finite handler order. If an installed
+    # processor also uses infinity, stable sorting keeps this appended handler
+    # after it, so sanitization still owns the final request boundary.
+    handler_order = float("inf")  # type: ignore[assignment]
 
     def __init__(self, original_url: str) -> None:
         self._original_origin = url_origin(original_url)
diff --git a/tests/hermes_cli/test_urllib_security.py b/tests/hermes_cli/test_urllib_security.py
index 32d5ebd187a..d21ac3bb030 100644
--- a/tests/hermes_cli/test_urllib_security.py
+++ b/tests/hermes_cli/test_urllib_security.py
@@ -329,6 +329,8 @@ def test_installed_request_processor_cannot_resurrect_cross_origin_secret(
     _RecordingHandler.redirect_to = f"http://localhost:{sink.server_port}/sink"
 
     class SecretProcessor(urllib.request.BaseHandler):
+        handler_order = float("inf")  # type: ignore[assignment]
+
         def http_request(self, request):
             request.add_header("X-Installed-Secret", "must-not-cross")
             return request
@@ -481,6 +483,50 @@ def test_anthropic_profile_drops_x_api_key_on_redirect(monkeypatch):
     assert headers["accept"] == "application/json"
 
 
+def test_azure_catalog_probe_drops_api_key_and_bearer_on_redirect():
+    from hermes_cli import azure_detect
+
+    source = _server()
+    sink = _server()
+    _RecordingHandler.requests = []
+    _RecordingHandler.redirect_status = 302
+    _RecordingHandler.redirect_to = f"http://localhost:{sink.server_port}/sink"
+    try:
+        status, body = azure_detect._http_get_json(
+            f"http://127.0.0.1:{source.server_port}/redirect", "azure-secret", timeout=3
+        )
+    finally:
+        source.shutdown()
+        sink.shutdown()
+
+    assert status == 200
+    assert body == {"data": []}
+    _, headers = _RecordingHandler.requests[-1]
+    assert "authorization" not in headers
+    assert "api-key" not in headers
+
+
+def test_azure_anthropic_probe_drops_api_key_and_bearer_on_redirect():
+    from hermes_cli import azure_detect
+
+    sink = _server()
+    source = ThreadingHTTPServer(("127.0.0.1", 0), _LmStudioSourceHandler)
+    Thread(target=source.serve_forever, daemon=True).start()
+    _RecordingHandler.requests = []
+    _LmStudioSourceHandler.redirect_to = f"http://localhost:{sink.server_port}/sink"
+    try:
+        azure_detect._probe_anthropic_messages(
+            f"http://127.0.0.1:{source.server_port}", "azure-secret"
+        )
+    finally:
+        source.shutdown()
+        sink.shutdown()
+
+    _, headers = _RecordingHandler.requests[-1]
+    assert "authorization" not in headers
+    assert "api-key" not in headers
+
+
 def test_lmstudio_load_post_drops_bearer_on_redirect(monkeypatch):
     from hermes_cli import models