diff -r f1a25c088b8f Lib/shutil.py
--- a/Lib/shutil.py	Fri Nov 02 14:49:02 2012 +0100
+++ b/Lib/shutil.py	Fri Nov 02 16:43:35 2012 +0200
@@ -381,7 +381,8 @@
     names = []
     try:
         names = os.listdir(topfd)
-    except os.error:
+    except OSError as err:
+        err.filename = path
         onerror(os.listdir, path, sys.exc_info())
     for name in names:
         fullname = os.path.join(path, name)
@@ -403,6 +404,14 @@
                             os.rmdir(name, dir_fd=topfd)
                         except os.error:
                             onerror(os.rmdir, fullname, sys.exc_info())
+                    else:
+                        try:
+                            # symlinks to directories are forbidden,
+                            # see bug #1669
+                            raise OSError("Cannot call rmtree on a symbolic "
+                                          "link")
+                        except OSError:
+                            onerror(os.path.islink, fullname, sys.exc_info())
                 finally:
                     os.close(dirfd)
         else:
@@ -450,16 +459,18 @@
             onerror(os.lstat, path, sys.exc_info())
             return
         try:
-            if (stat.S_ISDIR(orig_st.st_mode) and
-                os.path.samestat(orig_st, os.fstat(fd))):
+            if os.path.samestat(orig_st, os.fstat(fd)):
                 _rmtree_safe_fd(fd, path, onerror)
                 try:
                     os.rmdir(path)
                 except os.error:
                     onerror(os.rmdir, path, sys.exc_info())
             else:
-                raise NotADirectoryError(20,
-                                         "Not a directory: '{}'".format(path))
+                try:
+                    # symlinks to directories are forbidden, see bug #1669
+                    raise OSError("Cannot call rmtree on a symbolic link")
+                except OSError:
+                    onerror(os.path.islink, path, sys.exc_info())
         finally:
             os.close(fd)
     else:
diff -r f1a25c088b8f Lib/test/test_shutil.py
--- a/Lib/test/test_shutil.py	Fri Nov 02 14:49:02 2012 +0100
+++ b/Lib/test/test_shutil.py	Fri Nov 02 16:43:35 2012 +0200
@@ -127,6 +127,15 @@
         os.symlink(dir_, link)
         self.assertRaises(OSError, shutil.rmtree, link)
         self.assertTrue(os.path.exists(dir_))
+        self.assertTrue(os.path.lexists(link))
+        errors = []
+        def onerror(*args):
+            errors.append(args)
+        shutil.rmtree(link, onerror=onerror)
+        self.assertEqual(len(errors), 1)
+        self.assertIs(errors[0][0], os.path.islink)
+        self.assertEqual(errors[0][1], link)
+        self.assertIsInstance(errors[0][2][1], OSError)
 
     @support.skip_unless_symlink
     def test_rmtree_works_on_symlinks(self):
@@ -153,7 +162,34 @@
     def test_rmtree_errors(self):
         # filename is guaranteed not to exist
         filename = tempfile.mktemp()
-        self.assertRaises(OSError, shutil.rmtree, filename)
+        self.assertRaises(FileNotFoundError, shutil.rmtree, filename)
+        # test that ignore_errors option is honoured
+        shutil.rmtree(filename, ignore_errors=True)
+
+        # existing file
+        tmpdir = self.mkdtemp()
+        write_file((tmpdir, "tstfile"), "")
+        filename = os.path.join(tmpdir, "tstfile")
+        with self.assertRaises(NotADirectoryError) as cm:
+            shutil.rmtree(filename)
+        self.assertEqual(cm.exception.filename, filename)
+        self.assertTrue(os.path.exists(filename))
+        # test that ignore_errors option is honoured
+        shutil.rmtree(filename, ignore_errors=True)
+        self.assertTrue(os.path.exists(filename))
+        errors = []
+        def onerror(*args):
+            errors.append(args)
+        shutil.rmtree(filename, onerror=onerror)
+        self.assertEqual(len(errors), 2)
+        self.assertIs(errors[0][0], os.listdir)
+        self.assertEqual(errors[0][1], filename)
+        self.assertIsInstance(errors[0][2][1], NotADirectoryError)
+        self.assertEqual(errors[0][2][1].filename, filename)
+        self.assertIs(errors[1][0], os.rmdir)
+        self.assertEqual(errors[1][1], filename)
+        self.assertIsInstance(errors[1][2][1], NotADirectoryError)
+        self.assertEqual(errors[1][2][1].filename, filename)
 
     # See bug #1071513 for why we don't run this on cygwin
     # and bug #1076467 for why we don't run this as root.