Was trying to install alembic in a virtualenv with pip , on and OSX 10.11 machine:

$ pip install alembic
Collecting alembic
(...)

Ended up with the following traceback:

Traceback (most recent call last):
  File "/Users/kev/venvs/test/lib/python2.7/site-packages/pip/basecommand.py", line 211, in main
    status = self.run(options, args)
  File "/Users/kev/venvs/test/lib/python2.7/site-packages/pip/commands/install.py", line 305, in run
    wb.build(autobuilding=True)
  File "/Users/kev/venvs/test/lib/python2.7/site-packages/pip/wheel.py", line 705, in build
    self.requirement_set.prepare_files(self.finder)
  File "/Users/kev/venvs/test/lib/python2.7/site-packages/pip/req/req_set.py", line 334, in prepare_files
    functools.partial(self._prepare_file, finder))
  File "/Users/kev/venvs/test/lib/python2.7/site-packages/pip/req/req_set.py", line 321, in _walk_req_to_install
    more_reqs = handler(req_to_install)
  File "/Users/kev/venvs/test/lib/python2.7/site-packages/pip/req/req_set.py", line 461, in _prepare_file
    req_to_install.populate_link(finder, self.upgrade)
  File "/Users/kev/venvs/test/lib/python2.7/site-packages/pip/req/req_install.py", line 250, in populate_link
    self.link = finder.find_requirement(self, upgrade)
  File "/Users/kev/venvs/test/lib/python2.7/site-packages/pip/index.py", line 486, in find_requirement
    all_versions = self._find_all_versions(req.name)
  File "/Users/kev/venvs/test/lib/python2.7/site-packages/pip/index.py", line 444, in _find_all_versions
    for page in self._get_pages(url_locations, project_name):
  File "/Users/kev/venvs/test/lib/python2.7/site-packages/pip/index.py", line 641, in _get_pages
    page = self._get_page(location)
  File "/Users/kev/venvs/test/lib/python2.7/site-packages/pip/index.py", line 818, in _get_page
    return HTMLPage.get_page(link, session=self.session)
  File "/Users/kev/venvs/test/lib/python2.7/site-packages/pip/index.py", line 928, in get_page
    "Cache-Control": "max-age=600",
  File "/Users/kev/venvs/test/lib/python2.7/site-packages/pip/_vendor/requests/sessions.py", line 477, in get
    return self.request('GET', url, **kwargs)
  File "/Users/kev/venvs/test/lib/python2.7/site-packages/pip/download.py", line 373, in request
    return super(PipSession, self).request(method, url, *args, **kwargs)
  File "/Users/kev/venvs/test/lib/python2.7/site-packages/pip/_vendor/requests/sessions.py", line 465, in request
    resp = self.send(prep, **send_kwargs)
  File "/Users/kev/venvs/test/lib/python2.7/site-packages/pip/_vendor/requests/sessions.py", line 573, in send
    r = adapter.send(request, **kwargs)
  File "/Users/kev/venvs/test/lib/python2.7/site-packages/pip/_vendor/cachecontrol/adapter.py", line 46, in send
    resp = super(CacheControlAdapter, self).send(request, **kw)
  File "/Users/kev/venvs/test/lib/python2.7/site-packages/pip/_vendor/requests/adapters.py", line 370, in send
    timeout=timeout
  File "/Users/kev/venvs/test/lib/python2.7/site-packages/pip/_vendor/requests/packages/urllib3/connectionpool.py", line 544, in urlopen
    body=body, headers=headers)
  File "/Users/kev/venvs/test/lib/python2.7/site-packages/pip/_vendor/requests/packages/urllib3/connectionpool.py", line 344, in _make_request
    self._raise_timeout(err=e, url=url, timeout_value=conn.timeout)
  File "/Users/kev/venvs/test/lib/python2.7/site-packages/pip/_vendor/requests/packages/urllib3/connectionpool.py", line 314, in _raise_timeout
    if 'timed out' in str(err) or 'did not complete (read)' in str(err):  # Python 2.6
TypeError: __str__ returned non-string (type Error)

Looking into the connectionpool.py file revealed the context as being some sort of SSL-related validation.

By sheer luck I found the culprit in the name of the cryptography package.

After uninstalling it I was finally able to properly install alembic:

$ pip uninstall cryptography
Uninstalling cryptography-1.1:
(...)
Proceed (y/n)? y
  Successfully uninstalled cryptography-1.1

$ pip install alembic
Collecting alembic
(...)
Successfully installed alembic-0.8.3

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