Trying to use POST-request to https://vk.com and sometimes library raise an error.
  File "library/vkApi.py", line 31, in post
    response = self.Opener.open(request)
  File "/usr/lib/python2.7/urllib2.py", line 404, in open
    response = self._open(req, data)
  File "/usr/lib/python2.7/urllib2.py", line 422, in _open
    '_open', req)
  File "/usr/lib/python2.7/urllib2.py", line 382, in _call_chain
    result = func(*args)
  File "/usr/lib/python2.7/urllib2.py", line 1222, in https_open
    return self.do_open(httplib.HTTPSConnection, req)
  File "/usr/lib/python2.7/urllib2.py", line 1184, in do_open
    raise URLError(err)
URLError: <urlopen error _ssl.c:489: The handshake operation timed out>

This exception appears randomly, connection is ok 100%. I tried it on different machines with python 2.7.4 and 2.7.3.

I would guess that if you did a network trace you'd find out there really was a packet that did not arrive (a timeout).  Note that detecting this is complicated by the fact that ssl is involved.  (I don't know the details, but I remember someone saying that more than one packet may be involved in something that looks like a single event at the OpenSSL level.)

It is certainly *possible* that there is a bug at the OpenSSL or (less likely) the _ssl module level, but the first step in debugging it would be to get that network trace, I think...

As I said, though, I'm not an expert in this area, perhaps someone who is will have other suggestions.

I'm closing this ticket. It's old and hasn't seen any activity in almost three years.