diff --git a/tests/test_stl.cpp b/tests/test_stl.cpp
index dd93d51d0..08456b3c0 100644
--- a/tests/test_stl.cpp
+++ b/tests/test_stl.cpp
@@ -454,6 +454,13 @@ TEST_SUBMODULE(stl, m) {
     // test_fs_path
     m.attr("has_filesystem") = true;
     m.def("parent_path", [](const std::filesystem::path &p) { return p.parent_path(); });
+    m.def("parent_paths", [](const std::vector<std::filesystem::path> &p) {
+        std::vector<std::filesystem::path> result;
+        for (const auto &i : p) {
+            result.push_back(i.parent_path());
+        }
+        return result;
+    });
 #endif
 
 #ifdef PYBIND11_TEST_VARIANT
diff --git a/tests/test_stl.py b/tests/test_stl.py
index d2d89420f..2c3172703 100644
--- a/tests/test_stl.py
+++ b/tests/test_stl.py
@@ -265,6 +265,11 @@ def test_fs_path(doc):
         doc(m.parent_path)
         == "parent_path(arg0: Union[os.PathLike, str, bytes]) -> Path"
     )
+    assert m.parent_paths(["foo/bar", "foo/baz"]) == [Path("foo"), Path("foo")]
+    assert (
+        doc(m.parent_paths)
+        == "parent_paths(arg0: list[Union[os.PathLike, str, bytes]]) -> list[Path]"
+    )
 
 
 @pytest.mark.skipif(not hasattr(m, "load_variant"), reason="no <variant>")