diff --git a/surfsense_backend/tests/unit/middleware/__init__.py b/surfsense_backend/tests/unit/middleware/__init__.py
new file mode 100644
index 000000000..e69de29bb
diff --git a/surfsense_backend/tests/unit/middleware/test_dedup_hitl_tool_calls.py b/surfsense_backend/tests/unit/middleware/test_dedup_hitl_tool_calls.py
new file mode 100644
index 000000000..add0105e4
--- /dev/null
+++ b/surfsense_backend/tests/unit/middleware/test_dedup_hitl_tool_calls.py
@@ -0,0 +1,41 @@
+import pytest
+from langchain_core.messages import AIMessage
+
+from app.agents.new_chat.middleware.dedup_tool_calls import (
+    DedupHITLToolCallsMiddleware,
+)
+
+pytestmark = pytest.mark.unit
+
+
+def _make_state(tool_calls: list[dict]) -> dict:
+    """Build a minimal agent state with one AIMessage carrying *tool_calls*."""
+    msg = AIMessage(content="", tool_calls=tool_calls)
+    return {"messages": [msg]}
+
+
+def test_duplicate_hitl_calls_reduced_to_first():
+    """When the LLM emits the same HITL tool call twice, only the first is kept."""
+    mw = DedupHITLToolCallsMiddleware()
+
+    state = _make_state(
+        [
+            {
+                "id": "call_1",
+                "name": "delete_calendar_event",
+                "args": {"event_title_or_id": "Doctor Appointment"},
+            },
+            {
+                "id": "call_2",
+                "name": "delete_calendar_event",
+                "args": {"event_title_or_id": "Doctor Appointment"},
+            },
+        ]
+    )
+
+    result = mw.after_model(state, runtime=None)  # type: ignore[arg-type]
+
+    assert result is not None, "Expected middleware to return updated state"
+    updated_calls = result["messages"][0].tool_calls
+    assert len(updated_calls) == 1
+    assert updated_calls[0]["id"] == "call_1"