diff --git a/Lib/test/test_shutil.py b/Lib/test/test_shutil.py
index c0b48ea306b71ed..783fe1868249148 100644
--- a/Lib/test/test_shutil.py
+++ b/Lib/test/test_shutil.py
@@ -2729,7 +2729,9 @@ def test_environ_path_cwd(self):
                 self.assertIsNone(rv)
 
                 # look in current directory
-                with os_helper.change_cwd(self.dir):
+                with os_helper.change_cwd(self.dir), \
+                     unittest.mock.patch('shutil._win_path_needs_curdir',
+                                         return_value=True):
                     rv = shutil.which(self.file)
                     self.assertEqual(rv, expected_cwd)
 
diff --git a/Misc/NEWS.d/next/Tests/2026-11-03-22-45-00.gh-issue-156376.Wq7rKe.rst b/Misc/NEWS.d/next/Tests/2026-11-03-22-45-00.gh-issue-156376.Wq7rKe.rst
new file mode 100644
index 000000000000000..73bb4f482df29cb
--- /dev/null
+++ b/Misc/NEWS.d/next/Tests/2026-11-03-22-45-00.gh-issue-156376.Wq7rKe.rst
@@ -0,0 +1,3 @@
+Fix ``test_shutil.test_environ_path_cwd`` on Windows, which relied on the
+user's ``NoDefaultCurrentDirectoryInExePath`` environment setting and was
+therefore non-deterministic.