I think I might have found a related/real world example.

I'm on a mac with OSX-10.10.3 and "test_ssl" passes, but when I try to install jupyter_notebook it attempts to download some css, and gives what looks like an identical error to the first one, in the initial report (test_protocol_sslv23). The download works fine in 2.7 and 3.4:

>>> sys.version
'3.5.0a4 (v3.5.0a4:413e0e0004f4, Apr 19 2015, 14:19:25) \n[GCC 4.2.1 (Apple Inc. build 5666) (dot 3)]'

>>> ssl.OPENSSL_VERSION
'OpenSSL 0.9.8zd 8 Jan 2015'

>>> urllib.request.urlopen("https://cdn.jupyter.org/notebook/4.0.0-dev/style/style.min.css")

Traceback (most recent call last):
  File "/Library/Frameworks/Python.framework/Versions/3.5/lib/python3.5/urllib/request.py", line 1239, in do_open
    h.request(req.get_method(), req.selector, req.data, headers)
  File "/Library/Frameworks/Python.framework/Versions/3.5/lib/python3.5/http/client.py", line 1083, in request
    self._send_request(method, url, body, headers)
  File "/Library/Frameworks/Python.framework/Versions/3.5/lib/python3.5/http/client.py", line 1128, in _send_request
    self.endheaders(body)
  File "/Library/Frameworks/Python.framework/Versions/3.5/lib/python3.5/http/client.py", line 1079, in endheaders
    self._send_output(message_body)
  File "/Library/Frameworks/Python.framework/Versions/3.5/lib/python3.5/http/client.py", line 911, in _send_output
    self.send(msg)
  File "/Library/Frameworks/Python.framework/Versions/3.5/lib/python3.5/http/client.py", line 854, in send
    self.connect()
  File "/Library/Frameworks/Python.framework/Versions/3.5/lib/python3.5/http/client.py", line 1237, in connect
    server_hostname=server_hostname)
  File "/Library/Frameworks/Python.framework/Versions/3.5/lib/python3.5/ssl.py", line 376, in wrap_socket
    _context=self)
  File "/Library/Frameworks/Python.framework/Versions/3.5/lib/python3.5/ssl.py", line 747, in __init__
    self.do_handshake()
  File "/Library/Frameworks/Python.framework/Versions/3.5/lib/python3.5/ssl.py", line 983, in do_handshake
    self._sslobj.do_handshake()
  File "/Library/Frameworks/Python.framework/Versions/3.5/lib/python3.5/ssl.py", line 628, in do_handshake
    self._sslobj.do_handshake()
ssl.SSLError: [SSL: SSLV3_ALERT_HANDSHAKE_FAILURE] sslv3 alert handshake failure (_ssl.c:634)