diff --git a/Lib/test/test_nturl2path.py b/Lib/test/test_nturl2path.py
index 1bd77efd99ef4f..28e550f4b357a5 100644
--- a/Lib/test/test_nturl2path.py
+++ b/Lib/test/test_nturl2path.py
@@ -73,7 +73,7 @@ def test_pathname2url(self):
         for url in urls:
             self.assertEqual(fn(nturl2path.url2pathname(url)), url)
 
-    def test_url2pathname_win(self):
+    def test_url2pathname(self):
         fn = nturl2path.url2pathname
         self.assertEqual(fn('/C:/'), 'C:\\')
         self.assertEqual(fn("///C|"), 'C:')
diff --git a/Lib/test/test_urllib.py b/Lib/test/test_urllib.py
index d26e35a24632ae..b8ef50e8f6c339 100644
--- a/Lib/test/test_urllib.py
+++ b/Lib/test/test_urllib.py
@@ -1523,26 +1523,26 @@ def test_quoting(self):
     def test_pathname2url_win(self):
         # Test special prefixes are correctly handled in pathname2url()
         fn = urllib.request.pathname2url
-        self.assertEqual(fn('\\\\?\\C:\\dir'), '///C:/dir')
-        self.assertEqual(fn('\\\\?\\unc\\server\\share\\dir'), '/server/share/dir')
+        self.assertEqual(fn('\\\\?\\C:\\dir'), '//?/C:/dir')
+        self.assertEqual(fn('\\\\?\\unc\\server\\share\\dir'), '//?/unc/server/share/dir')
         self.assertEqual(fn("C:"), '///C:')
-        self.assertEqual(fn("C:\\"), '///C:')
+        self.assertEqual(fn("C:\\"), '///C:/')
         self.assertEqual(fn('C:\\a\\b.c'), '///C:/a/b.c')
         self.assertEqual(fn('C:\\a\\b%#c'), '///C:/a/b%25%23c')
         self.assertEqual(fn('C:\\a\\b\xe9'), '///C:/a/b%C3%A9')
         self.assertEqual(fn('C:\\foo\\bar\\spam.foo'), "///C:/foo/bar/spam.foo")
         # Long drive letter
-        self.assertRaises(IOError, fn, "XX:\\")
+        self.assertEqual(fn("XX:\\"), "file:XX:/")
         # No drive letter
         self.assertEqual(fn("\\folder\\test\\"), '/folder/test/')
-        self.assertEqual(fn("\\\\folder\\test\\"), '////folder/test/')
-        self.assertEqual(fn("\\\\\\folder\\test\\"), '/////folder/test/')
-        self.assertEqual(fn('\\\\some\\share\\'), '////some/share/')
-        self.assertEqual(fn('\\\\some\\share\\a\\b.c'), '////some/share/a/b.c')
-        self.assertEqual(fn('\\\\some\\share\\a\\b%#c\xe9'), '////some/share/a/b%25%23c%C3%A9')
+        self.assertEqual(fn("\\\\folder\\test\\"), '//folder/test/')
+        self.assertEqual(fn("\\\\\\folder\\test\\"), '///folder/test/')
+        self.assertEqual(fn('\\\\some\\share\\'), '//some/share/')
+        self.assertEqual(fn('\\\\some\\share\\a\\b.c'), '//some/share/a/b.c')
+        self.assertEqual(fn('\\\\some\\share\\a\\b%#c\xe9'), '//some/share/a/b%25%23c%C3%A9')
         # Round-tripping
         urls = ['///C:',
-                '/////folder/test/',
+                '//folder/test/',
                 '///C:/foo/bar/spam.foo']
         for url in urls:
             self.assertEqual(fn(urllib.request.url2pathname(url)), url)
@@ -1563,7 +1563,7 @@ def test_url2pathname_win(self):
         self.assertEqual(fn("///C|"), 'C:')
         self.assertEqual(fn("///C:"), 'C:')
         self.assertEqual(fn('///C:/'), 'C:\\')
-        self.assertEqual(fn('/C|//'), 'C:\\')
+        self.assertEqual(fn('/C|//'), 'C:\\\\')
         self.assertEqual(fn('///C|/path'), 'C:\\path')
         # No DOS drive
         self.assertEqual(fn("///C/test/"), '\\\\\\C\\test\\')
@@ -1575,7 +1575,7 @@ def test_url2pathname_win(self):
         self.assertEqual(fn('///C|/path/to/file'), 'C:\\path\\to\\file')
         self.assertEqual(fn("///C|/foo/bar/spam.foo"), 'C:\\foo\\bar\\spam.foo')
         # Non-ASCII drive letter
-        self.assertRaises(IOError, fn, "///\u00e8|/")
+        self.assertEqual(fn("///\u00e8|/"), "\\\u00e8|\\")
         # UNC paths
         self.assertEqual(fn('//server/path/to/file'), '\\\\server\\path\\to\\file')
         self.assertEqual(fn('////server/path/to/file'), '\\\\server\\path\\to\\file')
@@ -1585,7 +1585,7 @@ def test_url2pathname_win(self):
         self.assertEqual(fn('//localhost/C|/path/to/file'), 'C:\\path\\to\\file')
         # Round-tripping
         paths = ['C:',
-                 r'\\\C\test\\',
+                 r'\C\test\\',
                  r'C:\foo\bar\spam.foo']
         for path in paths:
             self.assertEqual(fn(urllib.request.pathname2url(path)), path)