I have a somewhat similar issue; an in-house Zope product is retrieving some information from a remote URL. If I hit the same URL from the command line on the zope server (using wget), it works fine. When Zope hits it, it gets a Bad Gateway error from the remote (Apache + Jboss) server. Will post back here with anything I find out, maybe it will help you.
For both you and Jacob I'd recommend getting a packet sniffer up and running. It looks like the requests your python code is emitting are not the same as the ones that, for example, wget is emitting.
For Joshua only: are you sure the SSL server you're trying to connect to is alive and responding well? Do you have to do a POST or woulda GET suffice? If the latter, then try using urllib2 instead of httplib. Also, can you let us see the full traceback you get when the error occurs?
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