diff --git a/news/8658.bugfix b/news/8658.bugfix
new file mode 100644
index 00000000000..6e43c8b3c0e
--- /dev/null
+++ b/news/8658.bugfix
@@ -0,0 +1,2 @@
+Only converts Windows path to unicode on Python 2 to avoid regressions when a
+POSIX environment does not configure the file system encoding correctly.
diff --git a/src/pip/_internal/utils/misc.py b/src/pip/_internal/utils/misc.py
index 24a7455628d..80b90c81816 100644
--- a/src/pip/_internal/utils/misc.py
+++ b/src/pip/_internal/utils/misc.py
@@ -134,7 +134,7 @@ def get_prog():
 # Retry every half second for up to 3 seconds
 @retry(stop_max_delay=3000, wait_fixed=500)
 def rmtree(dir, ignore_errors=False):
-    # type: (Text, bool) -> None
+    # type: (AnyStr, bool) -> None
     shutil.rmtree(dir, ignore_errors=ignore_errors,
                   onerror=rmtree_errorhandler)
 
diff --git a/src/pip/_internal/utils/temp_dir.py b/src/pip/_internal/utils/temp_dir.py
index 03aa8286670..d2c42feea28 100644
--- a/src/pip/_internal/utils/temp_dir.py
+++ b/src/pip/_internal/utils/temp_dir.py
@@ -4,12 +4,14 @@
 import itertools
 import logging
 import os.path
+import sys
 import tempfile
 from contextlib import contextmanager
 
 from pip._vendor.contextlib2 import ExitStack
 from pip._vendor.six import ensure_text
 
+from pip._internal.utils.compat import WINDOWS
 from pip._internal.utils.misc import enum, rmtree
 from pip._internal.utils.typing import MYPY_CHECK_RUNNING
 
@@ -193,10 +195,18 @@ def cleanup(self):
         """Remove the temporary directory created and reset state
         """
         self._deleted = True
-        if os.path.exists(self._path):
-            # Make sure to pass unicode on Python 2 to make the contents also
-            # use unicode, ensuring non-ASCII names and can be represented.
-            rmtree(ensure_text(self._path))
+        if not os.path.exists(self._path):
+            return
+        # Make sure to pass unicode on Python 2 to make the contents also
+        # use unicode, ensuring non-ASCII names and can be represented.
+        # This is only done on Windows because POSIX platforms use bytes
+        # natively for paths, and the bytes-text conversion omission avoids
+        # errors caused by the environment configuring encodings incorrectly.
+        if WINDOWS:
+            encoding = sys.getfilesystemencoding()
+            rmtree(ensure_text(self._path, encoding=encoding))
+        else:
+            rmtree(self._path)
 
 
 class AdjacentTempDirectory(TempDirectory):