diff --git a/Lib/test/test_zoneinfo/test_zoneinfo.py b/Lib/test/test_zoneinfo/test_zoneinfo.py
index 82041a2b488334..ae921f7432c466 100644
--- a/Lib/test/test_zoneinfo/test_zoneinfo.py
+++ b/Lib/test/test_zoneinfo/test_zoneinfo.py
@@ -1543,13 +1543,20 @@ class TzPathTest(TzPathUserMixin, ZoneInfoTestBase):
     @contextlib.contextmanager
     def python_tzpath_context(value):
         path_var = "PYTHONTZPATH"
+        unset_env_sentinel = object()
+        old_env = unset_env_sentinel
         try:
             with OS_ENV_LOCK:
                 old_env = os.environ.get(path_var, None)
                 os.environ[path_var] = value
                 yield
         finally:
-            if old_env is None:
+            if old_env is unset_env_sentinel:
+                # In this case, `old_env` was never retrieved from the
+                # environment for whatever reason, so there's no need to
+                # reset the environment TZPATH.
+                pass
+            elif old_env is None:
                 del os.environ[path_var]
             else:
                 os.environ[path_var] = old_env  # pragma: nocover
diff --git a/Misc/NEWS.d/next/Tests/2023-03-08-13-54-20.gh-issue-102537.Vfplpb.rst b/Misc/NEWS.d/next/Tests/2023-03-08-13-54-20.gh-issue-102537.Vfplpb.rst
new file mode 100644
index 00000000000000..94d160dd4127a6
--- /dev/null
+++ b/Misc/NEWS.d/next/Tests/2023-03-08-13-54-20.gh-issue-102537.Vfplpb.rst
@@ -0,0 +1,2 @@
+Adjust the error handling strategy in
+``test_zoneinfo.TzPathTest.python_tzpath_context``. Patch by Paul Ganssle.