diff --git a/src/crewai/crew.py b/src/crewai/crew.py
index d4b14e833..afa27b97a 100644
--- a/src/crewai/crew.py
+++ b/src/crewai/crew.py
@@ -1034,7 +1034,7 @@ class Crew(FlowTrackable, BaseModel):
         context = (
             aggregate_raw_outputs_from_task_outputs(task_outputs)
             if task.context is NOT_SPECIFIED
-            else aggregate_raw_outputs_from_tasks(task.context)
+            else aggregate_raw_outputs_from_tasks(cast(List["Task"], task.context))
         )
         return context
 
diff --git a/tests/test_task_context_type_annotation.py b/tests/test_task_context_type_annotation.py
index ad4e22730..2eca3b99a 100644
--- a/tests/test_task_context_type_annotation.py
+++ b/tests/test_task_context_type_annotation.py
@@ -81,8 +81,8 @@ class TestTaskContextTypeAnnotation:
         task_with_empty_list = Task(description="Task 3", expected_output="Output 3", context=[])
         
         assert task_with_not_specified.context is NOT_SPECIFIED
-        assert not (task_with_none.context is NOT_SPECIFIED)
-        assert not (task_with_empty_list.context is NOT_SPECIFIED)
+        assert task_with_none.context is not NOT_SPECIFIED
+        assert task_with_empty_list.context is not NOT_SPECIFIED
 
     def test_task_context_repr_shows_not_specified(self):
         """Test that NOT_SPECIFIED has a proper string representation."""