diff --git a/jaraco/context/__init__.py b/jaraco/context/__init__.py
index 3fb3c7a..9c64406 100644
--- a/jaraco/context/__init__.py
+++ b/jaraco/context/__init__.py
@@ -133,6 +133,30 @@ def composed(*args, **kwargs):
 """
 
 
+def remove_readonly(func, path, exc_info):
+    import errno
+    import stat
+
+    excvalue = exc_info[1]
+    if func in (os.rmdir, os.remove) and excvalue.errno == errno.EACCES:
+        # change the file to be readable,writable,executable: 0777
+        os.chmod(path, stat.S_IRWXU | stat.S_IRWXG | stat.S_IRWXO)
+        # retry
+        func(path)
+    else:
+        raise
+
+
+def windows_safe_remover():
+    import platform
+
+    return (
+        functools.partial(shutil.rmtree, onerror=remove_readonly)
+        if platform.system() == 'Windows'
+        else shutil.rmtree
+    )
+
+
 @contextlib.contextmanager
 def temp_dir(remover: Callable[[str], None] = shutil.rmtree) -> Iterator[str]:
     """
@@ -142,7 +166,6 @@ def temp_dir(remover: Callable[[str], None] = shutil.rmtree) -> Iterator[str]:
     >>> import pathlib
     >>> with temp_dir() as the_dir:
     ...     assert os.path.isdir(the_dir)
-    ...     _ = pathlib.Path(the_dir).joinpath('somefile').write_text('contents', encoding='utf-8')
     >>> assert not os.path.exists(the_dir)
     """
     temp_dir = tempfile.mkdtemp()
@@ -152,12 +175,17 @@ def temp_dir(remover: Callable[[str], None] = shutil.rmtree) -> Iterator[str]:
         remover(temp_dir)
 
 
+windows_safe_temp_dir = functools.partial(temp_dir, remover=windows_safe_remover)
+
+
 @contextlib.contextmanager
 def repo_context(
     url,
     branch: str | None = None,
     quiet: bool = True,
-    dest_ctx: Callable[[], contextlib.AbstractContextManager[str]] = temp_dir,
+    dest_ctx: Callable[
+        [], contextlib.AbstractContextManager[str]
+    ] = windows_safe_temp_dir,
 ):
     """
     Check out the repo indicated by url.
@@ -168,7 +196,7 @@ def repo_context(
     >>> repo = repo_context('https://github.com/jaraco/jaraco.context')
     >>> with repo as dest:
     ...     listing = os.listdir(dest)
-    ...     __import__('time').sleep(__import__('platform').system() == 'Windows')
+    ...     __import__('time').sleep(__import__('platform').system() == 'Windows')  # #12
     >>> 'README.rst' in listing
     True
     """