diff --git a/src/crewai/crew.py b/src/crewai/crew.py
index 5d4b9ff79..06256e7a5 100644
--- a/src/crewai/crew.py
+++ b/src/crewai/crew.py
@@ -762,7 +762,7 @@ class Crew(BaseModel):
                     context=context,
                     tools=tools_for_task,
                 )
-                task_outputs = [task_output]
+                task_outputs.append(task_output)
                 self._process_task_result(task, task_output)
                 self._store_execution_log(task, task_output, task_index, was_replayed)
 
@@ -783,7 +783,7 @@ class Crew(BaseModel):
             task_outputs = self._process_async_tasks(futures, was_replayed)
             futures.clear()
 
-        previous_output = task_outputs[task_index - 1] if task_outputs else None
+        previous_output = task_outputs[0] if task_outputs else None
         if previous_output is not None and not task.should_execute(previous_output):
             self._logger.log(
                 "debug",
@@ -905,11 +905,11 @@ class Crew(BaseModel):
             )
 
     def _create_crew_output(self, task_outputs: List[TaskOutput]) -> CrewOutput:
-        if len(task_outputs) != 1:
-            raise ValueError(
-                "Something went wrong. Kickoff should return only one task output."
-            )
-        final_task_output = task_outputs[0]
+        # Use the last task output as the final output
+        final_task_output = task_outputs[-1] if task_outputs else None
+        if not final_task_output:
+            raise ValueError("No task outputs available to create crew output.")
+            
         final_string_output = final_task_output.raw
         self._finish_execution(final_string_output)
         token_usage = self.calculate_usage_metrics()
@@ -918,7 +918,7 @@ class Crew(BaseModel):
             raw=final_task_output.raw,
             pydantic=final_task_output.pydantic,
             json_dict=final_task_output.json_dict,
-            tasks_output=[task.output for task in self.tasks if task.output],
+            tasks_output=task_outputs,  # Use all task outputs directly
             token_usage=token_usage,
         )
 
diff --git a/tests/crew_test.py b/tests/crew_test.py
index 2f347a50e..18aa08e79 100644
--- a/tests/crew_test.py
+++ b/tests/crew_test.py
@@ -1989,6 +1989,97 @@ def test_tools_with_custom_caching():
             assert result.raw == "3"
 
 
+@pytest.mark.vcr(filter_headers=["authorization"])
+def test_multiple_tasks_with_conditional():
+    """Test that having multiple tasks before a conditional task works correctly."""
+    task1 = Task(
+        description="Research task 1",
+        expected_output="Research output",
+        agent=researcher,
+    )
+    task2 = Task(
+        description="Research task 2",
+        expected_output="Research output",
+        agent=researcher,
+    )
+    
+    def condition_func(task_output: TaskOutput) -> bool:
+        return "success" in task_output.raw.lower()
+    
+    task3 = ConditionalTask(
+        description="Conditional task that runs if previous task succeeded",
+        expected_output="Conditional output",
+        agent=writer,
+        condition=condition_func,
+    )
+
+    crew = Crew(
+        agents=[researcher, writer],
+        tasks=[task1, task2, task3],
+    )
+
+    # Mock task outputs
+    mock_success = TaskOutput(
+        description="Mock success",
+        raw="Success output",
+        agent=researcher.role,
+    )
+    
+    # Set up mocks for task execution
+    with patch.object(Task, "execute_sync", return_value=mock_success) as mock_execute:
+        result = crew.kickoff()
+        # Verify all tasks were executed (no IndexError)
+        assert mock_execute.call_count == 3
+        assert len(result.tasks_output) == 3
+
+@pytest.mark.vcr(filter_headers=["authorization"])
+def test_multiple_conditional_tasks():
+    """Test that having multiple conditional tasks in sequence works correctly."""
+    task1 = Task(
+        description="Initial research task",
+        expected_output="Research output",
+        agent=researcher,
+    )
+    
+    def condition1(task_output: TaskOutput) -> bool:
+        return "success" in task_output.raw.lower()
+    
+    def condition2(task_output: TaskOutput) -> bool:
+        return "proceed" in task_output.raw.lower()
+    
+    task2 = ConditionalTask(
+        description="First conditional task",
+        expected_output="Conditional output 1",
+        agent=writer,
+        condition=condition1,
+    )
+    
+    task3 = ConditionalTask(
+        description="Second conditional task",
+        expected_output="Conditional output 2",
+        agent=writer,
+        condition=condition2,
+    )
+
+    crew = Crew(
+        agents=[researcher, writer],
+        tasks=[task1, task2, task3],
+    )
+
+    # Mock different task outputs to test conditional logic
+    mock_success = TaskOutput(
+        description="Mock success",
+        raw="Success and proceed output",
+        agent=researcher.role,
+    )
+    
+    # Set up mocks for task execution
+    with patch.object(Task, "execute_sync", return_value=mock_success) as mock_execute:
+        result = crew.kickoff()
+        # Verify all tasks were executed (no IndexError)
+        assert mock_execute.call_count == 3
+        assert len(result.tasks_output) == 3
+
 @pytest.mark.vcr(filter_headers=["authorization"])
 def test_using_contextual_memory():
     from unittest.mock import patch