The python libraries like urllib and httplib do not support ssl through a proxy. Urllib2 supports http through a proxy or https alone, but not https through a proxy. A while ago my wife complained to me that perl had trouble w/https. I was surprised since perl has a lot of networking libraries. Preferring python, I took a look a python and found the same problem. Eventually I figured out what python was missing: tunnelling. Though she may _coax_ me to port the code to perl, I'm writing it first in my favorite language. Pytunnel offers a tunnel that can be used for (among other things) tunnelling the ssl through a proxy. I'd be willing to offer suggestions or myself add the necessary code to urllib2. Anyone know how one goes about doing either? Your python code does not need to be changed except that the port and ip are supplied by the tunnel. Pytunnel uses a custom recvall which is like sendall but for recv. Recvall uses non-blocking sockets,timeouts and sleeps to attempt to get all of the data. If you have a bad network connection you'd want to set the timeout to be high. Recvall will probably be slower than a standard recvall. The code is rough and needs better error handling, comments and such. But since I got it working I decided to post it. You can find it at: http://aspn.activestate.com/ASPN/Cookbook/Python/Recipe/213238 Example of usage: import pytunnel,httplib def tunnel_this(ip,port): conn = httplib.HTTPSConnection(ip,port=port) conn.putrequest('GET', '/') conn.endheaders() response = conn.getresponse() print response.read() tunnel=pytunnel.build(host='login.yahoo.com',proxy_host='h1',proxy_user='u',proxy_pass='p') tunnel.run(tunnel_this)