diff -r b0fbaed45956 Lib/test/test_urllib.py
--- a/Lib/test/test_urllib.py	Tue Dec 17 21:13:16 2013 -0500
+++ b/Lib/test/test_urllib.py	Wed Dec 18 14:18:04 2013 +0200
@@ -48,45 +48,49 @@
 
 class FakeHTTPMixin(object):
     def fakehttp(self, fakedata):
-        class FakeSocket(io.BytesIO):
-            io_refs = 1
-
-            def sendall(self, data):
-                FakeHTTPConnection.buf = data
-
-            def makefile(self, *args, **kwds):
-                self.io_refs += 1
-                return self
-
-            def read(self, amt=None):
-                if self.closed:
-                    return b""
-                return io.BytesIO.read(self, amt)
-
-            def readline(self, length=None):
-                if self.closed:
-                    return b""
-                return io.BytesIO.readline(self, length)
-
-            def close(self):
-                self.io_refs -= 1
-                if self.io_refs == 0:
-                    io.BytesIO.close(self)
-
-        class FakeHTTPConnection(http.client.HTTPConnection):
-
-            # buffer to store data for verification in urlopen tests.
-            buf = None
-
-            def connect(self):
-                self.sock = FakeSocket(fakedata)
-
         self._connection_class = http.client.HTTPConnection
-        http.client.HTTPConnection = FakeHTTPConnection
+        http.client.HTTPConnection = fakehttp(fakedata)
 
     def unfakehttp(self):
         http.client.HTTPConnection = self._connection_class
 
+def fakehttp(fakedata):
+    class FakeSocket(io.BytesIO):
+        io_refs = 1
+
+        def sendall(self, data):
+            FakeHTTPConnection.buf = data
+
+        def makefile(self, *args, **kwds):
+            self.io_refs += 1
+            return self
+
+        def read(self, amt=None):
+            if self.closed:
+                return b""
+            return io.BytesIO.read(self, amt)
+
+        def readline(self, length=None):
+            if self.closed:
+                return b""
+            return io.BytesIO.readline(self, length)
+
+        def close(self):
+            self.io_refs -= 1
+            if self.io_refs == 0:
+                io.BytesIO.close(self)
+
+    class FakeHTTPConnection(http.client.HTTPConnection):
+
+        # buffer to store data for verification in urlopen tests.
+        buf = None
+        fakesock = FakeSocket(fakedata)
+
+        def connect(self):
+            self.sock = self.fakesock
+
+    return FakeHTTPConnection
+
 
 class urlopen_FileTests(unittest.TestCase):
     """Test urlopen() opening a temporary file.
diff -r b0fbaed45956 Lib/test/test_urllib2.py
--- a/Lib/test/test_urllib2.py	Tue Dec 17 21:13:16 2013 -0500
+++ b/Lib/test/test_urllib2.py	Wed Dec 18 14:18:04 2013 +0200
@@ -1,5 +1,6 @@
 import unittest
 from test import support
+from test import test_urllib
 
 import os
 import io
@@ -284,6 +285,7 @@
         self.data = None
         self.raise_on_endheaders = False
         self._tunnel_headers = {}
+        self.sock = None
 
     def __call__(self, host, timeout=socket._GLOBAL_DEFAULT_TIMEOUT):
         self.host = host
@@ -1371,6 +1373,23 @@
         self.assertEqual(len(http_handler.requests), 1)
         self.assertFalse(http_handler.requests[0].has_header(auth_header))
 
+    def test_http_closed(self):
+        """Test the connection is cleaned up when the response is closed"""
+        for (transfer, data) in (
+            ("Connection: close", b"data"),
+            ("Transfer-Encoding: chunked", b"4\r\ndata\r\n0\r\n\r\n"),
+            ("Content-Length: 4", b"data"),
+        ):
+            header = "HTTP/1.1 200 OK\r\n{}\r\n\r\n".format(transfer)
+            conn = test_urllib.fakehttp(header.encode() + data)
+            handler = urllib.request.AbstractHTTPHandler()
+            req = Request("http://dummy/")
+            req.timeout = None
+            with handler.do_open(conn, req) as resp:
+                resp.read()
+            self.assertTrue(conn.fakesock.closed,
+                "Connection not closed with {!r}".format(transfer))
+
 
 class MiscTests(unittest.TestCase):
 
diff -r b0fbaed45956 Lib/urllib/request.py
--- a/Lib/urllib/request.py	Tue Dec 17 21:13:16 2013 -0500
+++ b/Lib/urllib/request.py	Wed Dec 18 14:18:04 2013 +0200
@@ -1245,12 +1245,19 @@
             h.set_tunnel(req._tunnel_host, headers=tunnel_headers)
 
         try:
-            h.request(req.get_method(), req.selector, req.data, headers)
-        except socket.error as err: # timeout error
+            try:
+                h.request(req.get_method(), req.selector, req.data, headers)
+            except socket.error as err: # timeout error
+                raise URLError(err)
+            r = h.getresponse()
+        except:
             h.close()
-            raise URLError(err)
-        else:
-            r = h.getresponse()
+            raise
+        # Explicitly close the original socket object now
+        # to guarantee that the connection closes
+        # when the response closes its socket.makefile() object
+        if h.sock:
+            h.sock.close()
 
         r.url = req.get_full_url()
         # This line replaces the .msg attribute of the HTTPResponse