Issue 1:
Related to #1083, perhaps. Standard requests.get() for this particular site/page https://docs.apitools.com/2014/04/24/a-small-router-for-openresty.html results in:

>>> import requests
>>> requests.get('https://docs.apitools.com/2014/04/24/a-small-router-for-openresty.html')
Traceback (most recent call last):
File "<stdin>", line 1, in <module>
File "/Users/jaddison/.virtualenvs/techtown/lib/python2.7/site-packages/requests/api.py", line 55, in get
return request('get', url, **kwargs)
File "/Users/jaddison/.virtualenvs/techtown/lib/python2.7/site-packages/requests/api.py", line 44, in request
return session.request(method=method, url=url, **kwargs)
File "/Users/jaddison/.virtualenvs/techtown/lib/python2.7/site-packages/requests/sessions.py", line 383, in request
resp = self.send(prep, **send_kwargs)
File "/Users/jaddison/.virtualenvs/techtown/lib/python2.7/site-packages/requests/sessions.py", line 486, in send
r = adapter.send(request, **kwargs)
File "/Users/jaddison/.virtualenvs/techtown/lib/python2.7/site-packages/requests/adapters.py", line 385, in send
raise SSLError(e)
requests.exceptions.SSLError: [Errno 1] _ssl.c:504: error:14077410:SSL routines:SSL23_GET_SERVER_HELLO:sslv3 alert handshake failure

Using request-toolbelt's SSLAdapter to try various ssl versions, they all fail, it would seem... see following tracebacks.

TLSv1:

>>> adapter = SSLAdapter('TLSv1')
>>> s = requests.Session()
>>> s.mount('https://', adapter)
>>> s.get('https://docs.apitools.com/2014/04/24/a-small-router-for-openresty.html')
Traceback (most recent call last):
File "<stdin>", line 1, in <module>
File "/Users/jaddison/.virtualenvs/techtown/lib/python2.7/site-packages/requests/sessions.py", line 395, in get
return self.request('GET', url, **kwargs)
File "/Users/jaddison/.virtualenvs/techtown/lib/python2.7/site-packages/requests/sessions.py", line 383, in request
resp = self.send(prep, **send_kwargs)
File "/Users/jaddison/.virtualenvs/techtown/lib/python2.7/site-packages/requests/sessions.py", line 486, in send
r = adapter.send(request, **kwargs)
File "/Users/jaddison/.virtualenvs/techtown/lib/python2.7/site-packages/requests/adapters.py", line 385, in send
raise SSLError(e)
requests.exceptions.SSLError: [Errno 1] _ssl.c:504: error:14094410:SSL routines:SSL3_READ_BYTES:sslv3 alert handshake failure

SSLv3:

>>> adapter = SSLAdapter('SSLv3')
>>> s = requests.Session()
>>> s.mount('https://', adapter)
>>> s.get('https://docs.apitools.com/2014/04/24/a-small-router-for-openresty.html')
Traceback (most recent call last):
File "<stdin>", line 1, in <module>
File "/Users/jaddison/.virtualenvs/techtown/lib/python2.7/site-packages/requests/sessions.py", line 395, in get
return self.request('GET', url, **kwargs)
File "/Users/jaddison/.virtualenvs/techtown/lib/python2.7/site-packages/requests/sessions.py", line 383, in request
resp = self.send(prep, **send_kwargs)
File "/Users/jaddison/.virtualenvs/techtown/lib/python2.7/site-packages/requests/sessions.py", line 486, in send
r = adapter.send(request, **kwargs)
File "/Users/jaddison/.virtualenvs/techtown/lib/python2.7/site-packages/requests/adapters.py", line 385, in send
raise SSLError(e)
requests.exceptions.SSLError: [Errno 1] _ssl.c:504: error:14094410:SSL routines:SSL3_READ_BYTES:sslv3 alert handshake failure

SSLv2:

>>> adapter = SSLAdapter('SSLv2')
>>> s = requests.Session()
>>> s.mount('https://', adapter)
>>> s.get('https://docs.apitools.com/2014/04/24/a-small-router-for-openresty.html')
Traceback (most recent call last):
File "<stdin>", line 1, in <module>
File "/Users/jaddison/.virtualenvs/techtown/lib/python2.7/site-packages/requests/sessions.py", line 395, in get
return self.request('GET', url, **kwargs)
File "/Users/jaddison/.virtualenvs/techtown/lib/python2.7/site-packages/requests/sessions.py", line 383, in request
resp = self.send(prep, **send_kwargs)
File "/Users/jaddison/.virtualenvs/techtown/lib/python2.7/site-packages/requests/sessions.py", line 486, in send
r = adapter.send(request, **kwargs)
File "/Users/jaddison/.virtualenvs/techtown/lib/python2.7/site-packages/requests/adapters.py", line 378, in send
raise ConnectionError(e)
requests.exceptions.ConnectionError: HTTPSConnectionPool(host='docs.apitools.com', port=443): Max retries exceeded with url: /2014/04/24/a-small-router-for-openresty.html (Caused by <class 'socket.error'>: [Errno 54] Connection reset by peer)

Note the last one gives a Connection reset by peer error, which differs from the others, but I'm pretty sure SSLv2 isn't supported by the server anyhow.

For fun, I tried to pass through some more appropriate headers through on the last request as well:

>>> headers = {
... 'Accept': u"text/html,application/xhtml+xml,application/xml",
... 'User-Agent': u"Mozilla/5.0 (Macintosh; Intel Mac OS X 10_9_2) AppleWebKit/537.36 (KHTML, like Gecko) Chrome/34.0.1847.131 Safari/537.36",
... 'Accept-Encoding': u"gzip,deflate",
... 'Accept-Language': u"en-US,en;q=0.8"
... }
>>> adapter = SSLAdapter('SSLv2')
>>> s = requests.Session()
>>> s.mount('https://', adapter)
>>> s.get('https://docs.apitools.com/2014/04/24/a-small-router-for-openresty.html', headers=headers)
Traceback (most recent call last):
File "<stdin>", line 1, in <module>
File "/Users/jaddison/.virtualenvs/techtown/lib/python2.7/site-packages/requests/sessions.py", line 395, in get
return self.request('GET', url, **kwargs)
File "/Users/jaddison/.virtualenvs/techtown/lib/python2.7/site-packages/requests/sessions.py", line 383, in request
resp = self.send(prep, **send_kwargs)
File "/Users/jaddison/.virtualenvs/techtown/lib/python2.7/site-packages/requests/sessions.py", line 486, in send
r = adapter.send(request, **kwargs)
File "/Users/jaddison/.virtualenvs/techtown/lib/python2.7/site-packages/requests/adapters.py", line 378, in send
raise ConnectionError(e)
requests.exceptions.ConnectionError: HTTPSConnectionPool(host='docs.apitools.com', port=443): Max retries exceeded with url: /2014/04/24/a-small-router-for-openresty.html (Caused by <class 'socket.error'>: [Errno 54] Connection reset by peer)

No dice there either. Here's what the HTTPS connection info in Chrome on Mac looks like:

I'm not positive, but some googling indicates it's likely a cipher list issue, which is more urllib3, I think?

I tried to modify DEFAULT_CIPHER_LIST in pyopenssl, but started running into import errors. At this point it seemed like things were just broken, and there wasn't really a proper way to approach fixing this yet.

Version information:

OSX Mavericks

Python 2.7.5

OpenSSL 0.9.8y 5 Feb 2013 - (from python -c "import ssl; print ssl.OPENSSL_VERSION")

requests 2.2.1

requests-toolbelt 0.2.0

urllib3 1.8

Issue 2:
Many web servers use the Host header to match different sites, probably the most important HTTP header.

There is no Host entry in the response.request.headers, unless set explicitly when issuing the request.