diff -r 9fdeca5fdbf0 Lib/http/server.py
--- a/Lib/http/server.py	Mon Mar 28 06:13:52 2016 +0000
+++ b/Lib/http/server.py	Mon Mar 28 21:56:22 2016 +0200
@@ -741,7 +741,7 @@
         self.end_headers()
         return f
 
-    def translate_path(self, path):
+    def translate_path(self, path, os_path=os.path):
         """Translate a /-separated PATH to the local filename syntax.
 
         Components that mean special things to the local file system
@@ -763,10 +763,13 @@
         words = filter(None, words)
         path = os.getcwd()
         for word in words:
-            drive, word = os.path.splitdrive(word)
-            head, word = os.path.split(word)
+            while True:
+                drive, word = os_path.splitdrive(word)
+                if not drive:
+                    break
+            head, word = os_path.split(word)
             if word in (os.curdir, os.pardir): continue
-            path = os.path.join(path, word)
+            path = os_path.join(path, word)
         if trailing_slash:
             path += '/'
         return path
diff -r 9fdeca5fdbf0 Lib/test/test_httpservers.py
--- a/Lib/test/test_httpservers.py	Mon Mar 28 06:13:52 2016 +0000
+++ b/Lib/test/test_httpservers.py	Mon Mar 28 21:56:22 2016 +0200
@@ -12,6 +12,7 @@
 import sys
 import re
 import base64
+import ntpath
 import shutil
 import urllib.parse
 import html
@@ -908,6 +909,11 @@
         path = self.handler.translate_path('//filename?foo=bar')
         self.assertEqual(path, self.translated)
 
+    def test_windows_colon(self):
+        path = self.handler.translate_path('c:c:c:filename', os_path=ntpath)
+        path = path.replace(ntpath.sep, os.path.sep)
+        self.assertEqual(path, self.translated)
+
 
 class MiscTestCase(unittest.TestCase):
     def test_all(self):