diff --git a/Lib/contextlib.py b/Lib/contextlib.py
index 5b646fabca0..259194cdbbe 100644
--- a/Lib/contextlib.py
+++ b/Lib/contextlib.py
@@ -807,7 +807,12 @@ class chdir(AbstractContextManager):
         self._old_cwd = []
 
     def __enter__(self):
-        self._old_cwd.append(os.getcwd())
+        # try to chdir to the current cwd so that we preemptively fail if we are
+        # unnable to chdir back to it, see bpo-45545
+        old_cwd = os.getcwd()
+        os.chdir(old_cwd)
+
+        self._old_cwd.append(old_cwd)
         os.chdir(self.path)
 
     def __exit__(self, *excinfo):
diff --git a/Misc/NEWS.d/next/Library/2021-10-26-01-22-33.bpo-45545.QvsfXK.rst b/Misc/NEWS.d/next/Library/2021-10-26-01-22-33.bpo-45545.QvsfXK.rst
new file mode 100644
index 00000000000..e1fdbacfaaf
--- /dev/null
+++ b/Misc/NEWS.d/next/Library/2021-10-26-01-22-33.bpo-45545.QvsfXK.rst
@@ -0,0 +1,2 @@
+Premptively fail in :func:`contextdir.chdir` if we can't change back to the
+original directory.