diff --git a/docs/changelog/3302.bugfix.rst b/docs/changelog/3302.bugfix.rst
new file mode 100644
index 000000000..99249b6cc
--- /dev/null
+++ b/docs/changelog/3302.bugfix.rst
@@ -0,0 +1 @@
+- Add ``windir`` to the default list of Windows ``pass_env`` environment variables. - by :user:`kurtmckee`
diff --git a/src/tox/tox_env/api.py b/src/tox/tox_env/api.py
index 260252a68..b98ad3b0a 100644
--- a/src/tox/tox_env/api.py
+++ b/src/tox/tox_env/api.py
@@ -231,6 +231,7 @@ def _default_pass_env(self) -> list[str]:  # noqa: PLR6301
                     "USERPROFILE",  # needed for `os.path.expanduser()`
                     "PATHEXT",  # needed for discovering executables
                     "MSYSTEM",  # controls paths printed format
+                    "WINDIR",  # base path to system executables and DLLs
                 ],
             )
         else:  # pragma: win32 no cover
diff --git a/tests/session/cmd/test_show_config.py b/tests/session/cmd/test_show_config.py
index b852a40d0..f2272cda8 100644
--- a/tests/session/cmd/test_show_config.py
+++ b/tests/session/cmd/test_show_config.py
@@ -137,7 +137,9 @@ def test_pass_env_config_default(tox_project: ToxProjectCreator, stdout_is_atty:
         + (["SYSTEMDRIVE", "SYSTEMROOT", "TEMP"] if is_win else [])
         + (["TERM"] if stdout_is_atty else [])
         + (["TMP", "USERPROFILE"] if is_win else ["TMPDIR"])
-        + ["VIRTUALENV_*", "http_proxy", "https_proxy", "no_proxy"]
+        + ["VIRTUALENV_*"]
+        + (["WINDIR"] if is_win else [])
+        + ["http_proxy", "https_proxy", "no_proxy"]
     )
     assert pass_env == expected