diff --git a/src/mcp/server/fastmcp/utilities/func_metadata.py b/src/mcp/server/fastmcp/utilities/func_metadata.py
index 241100d31..2438a2a54 100644
--- a/src/mcp/server/fastmcp/utilities/func_metadata.py
+++ b/src/mcp/server/fastmcp/utilities/func_metadata.py
@@ -112,7 +112,7 @@ def convert_result(self, result: Any) -> Any:
         the structured output.
         """
         if isinstance(result, CallToolResult):
-            if self.output_schema is not None:
+            if self.output_schema is not None and not result.isError:
                 assert self.output_model is not None, "Output model must be set if output schema is defined"
                 self.output_model.model_validate(result.structuredContent)
             return result
diff --git a/tests/server/fastmcp/test_func_metadata.py b/tests/server/fastmcp/test_func_metadata.py
index 61e524290..facb9a3d2 100644
--- a/tests/server/fastmcp/test_func_metadata.py
+++ b/tests/server/fastmcp/test_func_metadata.py
@@ -878,6 +878,20 @@ def func_returning_annotated_tool_call_result() -> Annotated[CallToolResult, Per
         meta.convert_result(func_returning_annotated_tool_call_result())
 
 
+def test_tool_call_result_annotated_error_skips_structured_validation():
+    class PersonClass(BaseModel):
+        name: str
+
+    def func_returning_annotated_tool_call_result_error() -> Annotated[CallToolResult, PersonClass]:  # pragma: no cover
+        return CallToolResult(content=[], isError=True)
+
+    meta = func_metadata(func_returning_annotated_tool_call_result_error)
+    result = func_returning_annotated_tool_call_result_error()
+
+    assert meta.output_schema is not None
+    assert meta.convert_result(result) is result
+
+
 def test_tool_call_result_in_optional_is_rejected():
     """Test that Optional[CallToolResult] raises InvalidSignature"""