Demian Brecht added the comment:

Hi Alejandro,

I've spent a little time looking into this. I haven't been able to reproduce 
what you're seeing on Windows exactly, but I've encountered other issues along 
the same path using a local squid instance (localhost:4242):


from http.client import OK, HTTPConnection
import unittest

class TestProxy(unittest.TestCase):
    def test_proxy_tunnel_success(self):
        con = HTTPConnection('localhost', 4242)
        con.set_tunnel('www.example.com')
        con.request('GET', 'http://www.example.com')
        resp = con.getresponse()
        self.assertEqual(resp.code, 200)
        data = resp.read()
        con.close()

    def test_proxy_tunnel_failure(self):
        con = HTTPConnection('localhost', 4242)
        con.set_tunnel('www.example.com')
        con.request('GET', '/')
        resp = con.getresponse()
        self.assertEqual(resp.code, 200) # FAILS
        con.close()

if __name__ == '__main__':
    unittest.main()


As you can see with the test above, if I use the full URI, the request 
succeeds, but the relative path (as in your example) fails. My assumption is 
that these issues may be related to proxy server implementations, but I'd have 
to some further investigation before being able to go on more than a hunch (and 
I don't have time to do that tonight).

As a first step, could you please try using a full URI in your request and see 
if that produces the desired result?

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Python tracker <rep...@bugs.python.org>
<http://bugs.python.org/issue22041>
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