diff -r fc62fcd8e990 Lib/tempfile.py
--- a/Lib/tempfile.py	Fri Jan 24 11:44:16 2014 -0500
+++ b/Lib/tempfile.py	Fri Jan 24 19:52:38 2014 +0200
@@ -29,9 +29,9 @@
 
 import functools as _functools
 import warnings as _warnings
-import sys as _sys
 import io as _io
 import os as _os
+import shutil as _shutil
 import errno as _errno
 from random import Random as _Random
 
@@ -355,10 +355,13 @@
     underlying file object, without adding a __del__ method to the
     temporary file."""
 
+    # Set here since __del__ checks it
+    file = None
+    close_called = False
+
     def __init__(self, file, name, delete=True):
         self.file = file
         self.name = name
-        self.close_called = False
         self.delete = delete
 
     # NT provides delete-on-close as a primitive, so we don't need
@@ -370,14 +373,13 @@
         # that this must be referenced as self.unlink, because the
         # name TemporaryFileWrapper may also get None'd out before
         # __del__ is called.
-        unlink = _os.unlink
 
-        def close(self):
-            if not self.close_called:
+        def close(self, unlink=_os.unlink):
+            if not self.close_called and self.file is not None:
                 self.close_called = True
                 self.file.close()
                 if self.delete:
-                    self.unlink(self.name)
+                    unlink(self.name)
 
         # Need to ensure the file is deleted on __del__
         def __del__(self):
@@ -677,9 +679,11 @@
     in it are removed.
     """
 
+    # Handle mkdtemp raising an exception
+    name = None
+    _closed = False
+
     def __init__(self, suffix="", prefix=template, dir=None):
-        self._closed = False
-        self.name = None # Handle mkdtemp raising an exception
         self.name = mkdtemp(suffix, prefix, dir)
 
     def __repr__(self):
@@ -688,23 +692,18 @@
     def __enter__(self):
         return self.name
 
-    def cleanup(self, _warn=False):
+    def cleanup(self, _warn=False, _warnings=_warnings):
         if self.name and not self._closed:
             try:
+                _shutil.rmtree(self.name)
+            except (TypeError, AttributeError) as ex:
+                if "None" not in '%s' % (ex,):
+                    raise
                 self._rmtree(self.name)
-            except (TypeError, AttributeError) as ex:
-                # Issue #10188: Emit a warning on stderr
-                # if the directory could not be cleaned
-                # up due to missing globals
-                if "None" not in str(ex):
-                    raise
-                print("ERROR: {!r} while cleaning up {!r}".format(ex, self,),
-                      file=_sys.stderr)
-                return
             self._closed = True
-            if _warn:
-                self._warn("Implicitly cleaning up {!r}".format(self),
-                           ResourceWarning)
+            if _warn and _warnings.warn:
+                _warnings.warn("Implicitly cleaning up {!r}".format(self),
+                               ResourceWarning)
 
     def __exit__(self, exc, value, tb):
         self.cleanup()
@@ -713,36 +712,19 @@
         # Issue a ResourceWarning if implicit cleanup needed
         self.cleanup(_warn=True)
 
-    # XXX (ncoghlan): The following code attempts to make
-    # this class tolerant of the module nulling out process
-    # that happens during CPython interpreter shutdown
-    # Alas, it doesn't actually manage it. See issue #10188
-    _listdir = staticmethod(_os.listdir)
-    _path_join = staticmethod(_os.path.join)
-    _isdir = staticmethod(_os.path.isdir)
-    _islink = staticmethod(_os.path.islink)
-    _remove = staticmethod(_os.remove)
-    _rmdir = staticmethod(_os.rmdir)
-    _os_error = OSError
-    _warn = _warnings.warn
-
-    def _rmtree(self, path):
+    def _rmtree(self, path, _OSError=OSError, _sep=_os.path.sep,
+                _listdir=_os.listdir, _remove=_os.remove, _rmdir=_os.rmdir):
         # Essentially a stripped down version of shutil.rmtree.  We can't
         # use globals because they may be None'ed out at shutdown.
-        for name in self._listdir(path):
-            fullname = self._path_join(path, name)
-            try:
-                isdir = self._isdir(fullname) and not self._islink(fullname)
-            except self._os_error:
-                isdir = False
-            if isdir:
-                self._rmtree(fullname)
-            else:
+        if not isinstance(path, str):
+            _sep = _sep.encode()
+        try:
+            for name in _listdir(path):
+                fullname = path + _sep + name
                 try:
-                    self._remove(fullname)
-                except self._os_error:
-                    pass
-        try:
-            self._rmdir(path)
-        except self._os_error:
+                    _remove(fullname)
+                except _OSError:
+                    self._rmtree(fullname)
+            _rmdir(path)
+        except _OSError:
             pass
diff -r fc62fcd8e990 Lib/test/test_tempfile.py
--- a/Lib/test/test_tempfile.py	Fri Jan 24 11:44:16 2014 -0500
+++ b/Lib/test/test_tempfile.py	Fri Jan 24 19:52:38 2014 +0200
@@ -11,7 +11,7 @@
 import weakref
 
 import unittest
-from test import support
+from test import support, script_helper
 
 
 if hasattr(os, 'stat'):
@@ -1073,7 +1073,8 @@
         self.nameCheck(tmp.name, dir, pre, suf)
         # Create a subdirectory and some files
         if recurse:
-            self.do_create(tmp.name, pre, suf, recurse-1)
+            d1 = self.do_create(tmp.name, pre, suf, recurse-1)
+            d1.name = None
         with open(os.path.join(tmp.name, "test.txt"), "wb") as f:
             f.write(b"Hello world!")
         return tmp
@@ -1105,7 +1106,7 @@
     def test_cleanup_with_symlink_to_a_directory(self):
         # cleanup() should not follow symlinks to directories (issue #12464)
         d1 = self.do_create()
-        d2 = self.do_create()
+        d2 = self.do_create(recurse=0)
 
         # Symlink d1/foo -> d2
         os.symlink(d2.name, os.path.join(d1.name, "foo"))
@@ -1135,60 +1136,50 @@
         finally:
             os.rmdir(dir)
 
-    @unittest.expectedFailure # See issue #10188
     def test_del_on_shutdown(self):
         # A TemporaryDirectory may be cleaned up during shutdown
-        # Make sure it works with the relevant modules nulled out
         with self.do_create() as dir:
-            d = self.do_create(dir=dir)
-            # Mimic the nulling out of modules that
-            # occurs during system shutdown
-            modules = [os, os.path]
-            if has_stat:
-                modules.append(stat)
-            # Currently broken, so suppress the warning
-            # that is otherwise emitted on stdout
-            with support.captured_stderr() as err:
-                with NulledModules(*modules):
-                    d.cleanup()
-            # Currently broken, so stop spurious exception by
-            # indicating the object has already been closed
-            d._closed = True
-            # And this assert will fail, as expected by the
-            # unittest decorator...
-            self.assertFalse(os.path.exists(d.name),
-                        "TemporaryDirectory %s exists after cleanup" % d.name)
+            for mod in ('os', 'shutil', 'sys', 'tempfile', 'warnings'):
+                code = """if True:
+                    import os
+                    import shutil
+                    import sys
+                    import tempfile
+                    import warnings
+
+                    tmp = tempfile.TemporaryDirectory(dir={dir!r})
+                    sys.stdout.buffer.write(tmp.name.encode())
+
+                    tmp2 = os.path.join(tmp.name, 'test_dir')
+                    os.mkdir(tmp2)
+                    with open(os.path.join(tmp2, "test.txt"), "w") as f:
+                        f.write("Hello world!")
+
+                    {mod}.tmp = tmp
+
+                    warnings.filterwarnings("always", category=ResourceWarning)
+                    """.format(dir=dir, mod=mod)
+                rc, out, err = script_helper.assert_python_ok("-c", code)
+                tmp_name = out.decode().strip()
+                self.assertFalse(os.path.exists(tmp_name),
+                            "TemporaryDirectory %s exists after cleanup" % tmp_name)
+                # Two kinds of warning on shutdown
+                #   Issue 10188: may write to stderr if modules are nulled out
+                #   ResourceWarning will be triggered by __del__
 
     def test_warnings_on_cleanup(self):
-        # Two kinds of warning on shutdown
-        #   Issue 10888: may write to stderr if modules are nulled out
-        #   ResourceWarning will be triggered by __del__
+        # ResourceWarning will be triggered by __del__
         with self.do_create() as dir:
-            if os.sep != '\\':
-                # Embed a backslash in order to make sure string escaping
-                # in the displayed error message is dealt with correctly
-                suffix = '\\check_backslash_handling'
-            else:
-                suffix = ''
-            d = self.do_create(dir=dir, suf=suffix)
-
-            #Check for the Issue 10888 message
-            modules = [os, os.path]
-            if has_stat:
-                modules.append(stat)
-            with support.captured_stderr() as err:
-                with NulledModules(*modules):
-                    d.cleanup()
-            message = err.getvalue().replace('\\\\', '\\')
-            self.assertIn("while cleaning up",  message)
-            self.assertIn(d.name,  message)
+            d = self.do_create(dir=dir, recurse=3)
+            name = d.name
 
             # Check for the resource warning
             with support.check_warnings(('Implicitly', ResourceWarning), quiet=False):
                 warnings.filterwarnings("always", category=ResourceWarning)
-                d.__del__()
-            self.assertFalse(os.path.exists(d.name),
-                        "TemporaryDirectory %s exists after __del__" % d.name)
+                del d
+                support.gc_collect()
+            self.assertFalse(os.path.exists(name),
+                        "TemporaryDirectory %s exists after __del__" % name)
 
     def test_multiple_close(self):
         # Can be cleaned-up many times without error
diff -r fc62fcd8e990 Misc/NEWS
--- a/Misc/NEWS	Fri Jan 24 11:44:16 2014 -0500
+++ b/Misc/NEWS	Fri Jan 24 19:52:38 2014 +0200
@@ -50,6 +50,11 @@
 Library
 -------
 
+- Issue #19077: tempfile.TemporaryDirectory cleanup is now most likely
+  successful when called during nulling out of modules during shutdown.
+  Howere it still can throw a misleading exception if emitting a warning
+  fails.
+
 - Issue #20317: ExitStack.__exit__ could create a self-referential loop if an
   exception raised by a cleanup operation already had its context set
   correctly (for example, by the @contextmanager decorator). The infinite