Here's all the patch that should be necessary to do the upgrade.  Running test_ssl on 2.7 with 1.0.1g I do have a failure:

======================================================================
ERROR: test_socketserver (test.test_ssl.ThreadedTests)
Using a SocketServer to create and manage SSL connections.
----------------------------------------------------------------------
Traceback (most recent call last):
  File "P:\ath\to\2.7\cpython\lib\test\test_ssl.py", line 1179, in test_socketserver
    f = urllib.urlopen(url)
  File "P:\ath\to\2.7\cpython\lib\urllib.py", line 87, in urlopen
    return opener.open(url)
  File "P:\ath\to\2.7\cpython\lib\urllib.py", line 208, in open
    return getattr(self, name)(url)
  File "P:\ath\to\2.7\cpython\lib\urllib.py", line 437, in open_https
    h.endheaders(data)
  File "P:\ath\to\2.7\cpython\lib\httplib.py", line 969, in endheaders
    self._send_output(message_body)
  File "P:\ath\to\2.7\cpython\lib\httplib.py", line 829, in _send_output
    self.send(msg)
  File "P:\ath\to\2.7\cpython\lib\httplib.py", line 791, in send
    self.connect()
  File "P:\ath\to\2.7\cpython\lib\httplib.py", line 1176, in connect
    self.sock = ssl.wrap_socket(sock, self.key_file, self.cert_file)
  File "P:\ath\to\2.7\cpython\lib\ssl.py", line 392, in wrap_socket
    ciphers=ciphers)
  File "P:\ath\to\2.7\cpython\lib\ssl.py", line 148, in __init__
    self.do_handshake()
  File "P:\ath\to\2.7\cpython\lib\ssl.py", line 310, in do_handshake
    self._sslobj.do_handshake()
IOError: [Errno socket error] [Errno 1] _ssl.c:510: error:140770FC:SSL routines:
SSL23_GET_SERVER_HELLO:unknown protocol

----------------------------------------------------------------------

But this looks closely related to a failure that I have on this machine using 3.4 (which is probably the fault of the way this network is set up):

======================================================================
ERROR: test_socketserver (test.test_ssl.ThreadedTests)
Using a SocketServer to create and manage SSL connections.
----------------------------------------------------------------------
Traceback (most recent call last):
  File "P:\ath\to\3.4\cpython\lib\urllib\request.py", line 1189, in do_open
    h.request(req.get_method(), req.selector, req.data, headers)
  File "P:\ath\to\3.4\cpython\lib\http\client.py", line 1090, in request
    self._send_request(method, url, body, headers)
  File "P:\ath\to\3.4\cpython\lib\http\client.py", line 1128, in _send_request
    self.endheaders(body)
  File "P:\ath\to\3.4\cpython\lib\http\client.py", line 1086, in endheaders
    self._send_output(message_body)
  File "P:\ath\to\3.4\cpython\lib\http\client.py", line 924, in _send_output
    self.send(msg)
  File "P:\ath\to\3.4\cpython\lib\http\client.py", line 859, in send
    self.connect()
  File "P:\ath\to\3.4\cpython\lib\http\client.py", line 1221, in connect
    super().connect()
  File "P:\ath\to\3.4\cpython\lib\http\client.py", line 839, in connect
    self._tunnel()
  File "P:\ath\to\3.4\cpython\lib\http\client.py", line 822, in _tunnel
    message.strip()))
OSError: Tunnel connection failed: 403 Forbidden

During handling of the above exception, another exception occurred:

Traceback (most recent call last):
  File "P:\ath\to\3.4\cpython\lib\test\test_ssl.py",line 2315, in test_socketserver
    f = urllib.request.urlopen(url)
  File "P:\ath\to\3.4\cpython\lib\urllib\request.py", line 153, in urlopen
    return opener.open(url, data, timeout)
  File "P:\ath\to\3.4\cpython\lib\urllib\request.py", line 455, in open
    response = self._open(req, data)
  File "P:\ath\to\3.4\cpython\lib\urllib\request.py", line 473, in _open
    '_open', req)
  File "P:\ath\to\3.4\cpython\lib\urllib\request.py", line 433, in _call_chain
    result = func(*args)
  File "P:\ath\to\3.4\cpython\lib\urllib\request.py", line 1230, in https_open
    context=self._context, check_hostname=self._check_hostname)
  File "P:\ath\to\3.4\cpython\lib\urllib\request.py", line 1192, in do_open
    raise URLError(err)
urllib.error.URLError: <urlopen error Tunnel connection failed: 403 Forbidden>

----------------------------------------------------------------------

As such, I'll leave it to someone else to properly test this before committing.