diff --git a/tests/test_fix_message_list.py b/tests/test_fix_message_list.py
new file mode 100644
index 00000000..6e9348a4
--- /dev/null
+++ b/tests/test_fix_message_list.py
@@ -0,0 +1,45 @@
+import signal
+
+import pytest
+
+from cai.util import fix_message_list
+
+
+def test_fix_message_list_handles_multiple_tool_results_without_loop():
+    if not hasattr(signal, "SIGALRM"):
+        pytest.skip("SIGALRM is required for this infinite-loop regression test")
+
+    messages = [
+        {"role": "user", "content": "Run both tools"},
+        {
+            "role": "assistant",
+            "content": None,
+            "tool_calls": [
+                {
+                    "id": "call_one",
+                    "type": "function",
+                    "function": {"name": "first_tool", "arguments": "{}"},
+                },
+                {
+                    "id": "call_two",
+                    "type": "function",
+                    "function": {"name": "second_tool", "arguments": "{}"},
+                },
+            ],
+        },
+        {"role": "tool", "tool_call_id": "call_one", "content": "first result"},
+        {"role": "tool", "tool_call_id": "call_two", "content": "second result"},
+    ]
+
+    def fail_on_timeout(_signum, _frame):
+        raise TimeoutError("fix_message_list did not terminate")
+
+    previous_handler = signal.signal(signal.SIGALRM, fail_on_timeout)
+    signal.alarm(2)
+    try:
+        fixed_messages = fix_message_list(messages)
+    finally:
+        signal.alarm(0)
+        signal.signal(signal.SIGALRM, previous_handler)
+
+    assert fixed_messages == messages