diff --git a/src/uipath/_cli/_evals/mocks/llm_mocker.py b/src/uipath/_cli/_evals/mocks/llm_mocker.py
index aadfb45e9..2888a19b5 100644
--- a/src/uipath/_cli/_evals/mocks/llm_mocker.py
+++ b/src/uipath/_cli/_evals/mocks/llm_mocker.py
@@ -90,7 +90,11 @@ async def response(
         assert isinstance(self.context.strategy, LLMMockingStrategy)
 
         function_name = params.get("name") or func.__name__
-        if function_name in [x.name for x in self.context.strategy.tools_to_simulate]:
+        normalized_function_name = function_name.replace("_", " ").lower()
+        if normalized_function_name in [
+            x.name.replace("_", " ").lower()
+            for x in self.context.strategy.tools_to_simulate
+        ]:
             from uipath.platform import UiPath
             from uipath.platform.chat._llm_gateway_service import _cleanup_schema
 
diff --git a/src/uipath/_cli/_evals/mocks/mocks.py b/src/uipath/_cli/_evals/mocks/mocks.py
index ed8f1c3c6..793ddeb19 100644
--- a/src/uipath/_cli/_evals/mocks/mocks.py
+++ b/src/uipath/_cli/_evals/mocks/mocks.py
@@ -73,11 +73,12 @@ def clear_execution_context() -> None:
 
 
 def _normalize_tool_name(name: str) -> str:
-    """Normalize tool name by replacing underscores with spaces.
+    """Normalize tool name by replacing underscores with spaces and lowering case.
 
     Tool names may use spaces in configuration but underscores in execution.
+    Comparison is case-insensitive.
     """
-    return name.replace("_", " ")
+    return name.replace("_", " ").lower()
 
 
 def is_tool_simulated(tool_name: str) -> bool:
diff --git a/tests/cli/test_debug_simulation.py b/tests/cli/test_debug_simulation.py
index 61498ee19..12f561480 100644
--- a/tests/cli/test_debug_simulation.py
+++ b/tests/cli/test_debug_simulation.py
@@ -524,3 +524,37 @@ def test_handles_tool_name_normalization(self, temp_dir: str):
             assert is_tool_simulated("Web Search") is True
 
             clear_execution_context()
+
+    def test_handles_tool_name_case_insensitive(self, temp_dir: str):
+        """Test that tool name comparison is case-insensitive."""
+        config = {
+            "enabled": True,
+            "instructions": "Test",
+            "toolsToSimulate": [
+                {"name": "Web Reader"},
+                {"name": "Web Search"},
+            ],
+        }
+        simulation_path = Path(temp_dir) / "simulation.json"
+        with open(simulation_path, "w", encoding="utf-8") as f:
+            json.dump(config, f)
+
+        with patch("uipath._cli.cli_debug.Path.cwd", return_value=Path(temp_dir)):
+            mocking_ctx = load_simulation_config()
+            assert mocking_ctx is not None
+
+            from uipath._cli._evals._span_collection import ExecutionSpanCollector
+            from uipath._cli._evals.mocks.mocks import set_execution_context
+
+            span_collector = ExecutionSpanCollector()
+            set_execution_context(mocking_ctx, span_collector, "test-id")
+
+            # Case-insensitive matching should work
+            assert is_tool_simulated("web reader") is True
+            assert is_tool_simulated("WEB READER") is True
+            assert is_tool_simulated("Web reader") is True
+            assert is_tool_simulated("web search") is True
+            assert is_tool_simulated("WEB SEARCH") is True
+            assert is_tool_simulated("Non Existent Tool") is False
+
+            clear_execution_context()