diff --git a/tests/test_helptext.py b/tests/test_helptext.py
index b8aa3e47..c229a3d3 100644
--- a/tests/test_helptext.py
+++ b/tests/test_helptext.py
@@ -1,5 +1,6 @@
 import dataclasses
 import enum
+import os
 import pathlib
 from collections.abc import Callable
 from typing import Any, Dict, Generic, List, Optional, Tuple, TypeVar, Union, cast
@@ -562,3 +563,11 @@ def main2(x: Callable = nn.ReLU):
     assert "--x {fixed}" in helptext
     assert "(fixed to:" in helptext
     assert "torch" in helptext
+
+
+def test_pathlike() -> None:
+    def main(x: os.PathLike) -> None:
+        pass
+
+    helptext = get_helptext(main)
+    assert "--x PATH " in helptext
diff --git a/tests/test_tyro.py b/tests/test_tyro.py
index 1aafac0e..c7f8e536 100644
--- a/tests/test_tyro.py
+++ b/tests/test_tyro.py
@@ -2,6 +2,7 @@
 import copy
 import dataclasses
 import enum
+import os
 import pathlib
 from typing import (
     Any,
@@ -551,7 +552,7 @@ def main() -> argparse.ArgumentParser:
 
 
 def test_pathlike():
-    def main(x: os.PathLike, /) -> os.PathLike:
+    def main(x: os.PathLike) -> os.PathLike:
         return x
 
-    assert tyro.cli(main, args=["/dev/null"]) == pathlib.Path("/dev/null")
+    assert tyro.cli(main, args=["--x", "/dev/null"]) == pathlib.Path("/dev/null")