diff --git a/examples/python/bug_tests/payload_bug_on_replay/worker.py b/examples/python/bug_tests/payload_bug_on_replay/worker.py
new file mode 100644
index 000000000..673a25ab7
--- /dev/null
+++ b/examples/python/bug_tests/payload_bug_on_replay/worker.py
@@ -0,0 +1,32 @@
+from pydantic import BaseModel
+
+from hatchet_sdk import Context, Hatchet, ParentCondition
+
+
+class Input(BaseModel):
+    random_number: int
+
+
+class StepOutput(BaseModel):
+    should_cancel: bool
+
+
+hatchet = Hatchet(debug=True)
+
+payload_initial_cancel_bug_workflow = hatchet.workflow(
+    name="payload-initial-cancel-test",
+    input_validator=Input,
+)
+
+
+@payload_initial_cancel_bug_workflow.task()
+def step1(input: Input, ctx: Context) -> StepOutput:
+    return StepOutput(should_cancel=ctx.retry_count == 0)
+
+
+@payload_initial_cancel_bug_workflow.task(
+    parents=[step1],
+    cancel_if=[ParentCondition(parent=step1, expression="output.should_cancel")],
+)
+async def step2(input: Input, ctx: Context) -> StepOutput:
+    return StepOutput(should_cancel=False)
diff --git a/examples/python/worker.py b/examples/python/worker.py
index 24b71b8bc..3cd28f0b0 100644
--- a/examples/python/worker.py
+++ b/examples/python/worker.py
@@ -1,4 +1,7 @@
 from examples.affinity_workers.worker import affinity_worker_workflow
+from examples.bug_tests.payload_bug_on_replay.worker import (
+    payload_initial_cancel_bug_workflow,
+)
 from examples.bulk_fanout.worker import bulk_child_wf, bulk_parent_wf
 from examples.bulk_operations.worker import (
     bulk_replay_test_1,
@@ -75,6 +78,7 @@ def main() -> None:
             concurrency_cancel_newest_workflow,
             concurrency_cancel_in_progress_workflow,
             di_workflow,
+            payload_initial_cancel_bug_workflow,
             lifespan_task,
             simple,
             simple_durable,