diff --git a/task-sdk/pyproject.toml b/task-sdk/pyproject.toml
index 350f901ee17bc..4e4e86b6348c7 100644
--- a/task-sdk/pyproject.toml
+++ b/task-sdk/pyproject.toml
@@ -261,6 +261,9 @@ log_level = "INFO"
 filterwarnings = [
     "error::pytest.PytestCollectionWarning",
 ]
+markers = [
+    "flaky: mark test as flaky and rerun on failure",
+]
 python_files = [
     "test_*.py",
 ]
diff --git a/task-sdk/tests/task_sdk/execution_time/test_supervisor.py b/task-sdk/tests/task_sdk/execution_time/test_supervisor.py
index 15e412d552adc..6ce05fefa1188 100644
--- a/task-sdk/tests/task_sdk/execution_time/test_supervisor.py
+++ b/task-sdk/tests/task_sdk/execution_time/test_supervisor.py
@@ -350,6 +350,7 @@ def subprocess_main():
             ]
         )
 
+    @pytest.mark.flaky(reruns=3)
     def test_reopen_log_fd(self, captured_logs, client_with_ti_start):
         def subprocess_main():
             # This is run in the subprocess!
@@ -360,11 +361,12 @@ def subprocess_main():
 
             logs = comms.send(ResendLoggingFD())
             assert isinstance(logs, SentFDs)
-            fd = os.fdopen(logs.fds[0], "w")
             logging.root.info("Log on old socket")
-            json.dump({"level": "info", "event": "Log on new socket"}, fp=fd)
+            with os.fdopen(logs.fds[0], "w") as fd:
+                json.dump({"level": "info", "event": "Log on new socket"}, fp=fd)
+                fd.write("\n")
 
-        line = lineno() - 3  # Line the error should be on
+        line = lineno() - 5  # Line the error should be on
 
         proc = ActivitySubprocess.start(
             dag_rel_path=os.devnull,