So we've been running devpi internall for a few weeks, 1.1 and now 1.2. One thing we've seen occasionally is pip running into this SSLError below. Apache Bench doesn't show any oddities when we try to hit devpi directly. Our SSL settings are the same we use with all our internal sites. It's fronted by nginx: ssl on; ssl_certificate ***; ssl_certificate_key ***; ssl_prefer_server_ciphers on; ssl_session_cache shared:SSL:10m; add_header Strict-Transport-Security max-age=86400; Exception: Traceback (most recent call last): File "/home/travis/virtualenv/python2.7/local/lib/python2.7/site-packages/pip/basecommand.py", line 134, in main status = self.run(options, args) File "/home/travis/virtualenv/python2.7/local/lib/python2.7/site-packages/pip/commands/install.py", line 236, in run requirement_set.prepare_files(finder, force_root_egg_info=self.bundle, bundle=self.bundle) File "/home/travis/virtualenv/python2.7/local/lib/python2.7/site-packages/pip/req.py", line 1092, in prepare_files self.unpack_url(url, location, self.is_download) File "/home/travis/virtualenv/python2.7/local/lib/python2.7/site-packages/pip/req.py", line 1238, in unpack_url retval = unpack_http_url(link, location, self.download_cache, self.download_dir) File "/home/travis/virtualenv/python2.7/local/lib/python2.7/site-packages/pip/download.py", line 602, in unpack_http_url resp = _get_response_from_url(target_url, link) File "/home/travis/virtualenv/python2.7/local/lib/python2.7/site-packages/pip/download.py", line 638, in _get_response_from_url resp = urlopen(target_url) File "/home/travis/virtualenv/python2.7/local/lib/python2.7/site-packages/pip/download.py", line 176, in __call__ response = self.get_opener(scheme=scheme).open(url) File "/usr/lib/python2.7/urllib2.py", line 400, in open response = self._open(req, data) File "/usr/lib/python2.7/urllib2.py", line 418, in _open '_open', req) File "/usr/lib/python2.7/urllib2.py", line 378, in _call_chain result = func(*args) File "/home/travis/virtualenv/python2.7/local/lib/python2.7/site-packages/pip/download.py", line 155, in https_open return self.do_open(self.specialized_conn_class, req) File "/usr/lib/python2.7/urllib2.py", line 1180, in do_open r = h.getresponse(buffering=True) File "/usr/lib/python2.7/httplib.py", line 1030, in getresponse response.begin() File "/usr/lib/python2.7/httplib.py", line 407, in begin version, status, reason = self._read_status() File "/usr/lib/python2.7/httplib.py", line 365, in _read_status line = self.fp.readline() File "/usr/lib/python2.7/socket.py", line 447, in readline data = self._sock.recv(self._rbufsize) File "/usr/lib/python2.7/ssl.py", line 241, in recv return self.read(buflen) File "/usr/lib/python2.7/ssl.py", line 160, in read return self._sslobj.read(len) SSLError: The read operation timed ou t