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When attempting to use basic auth over https with a server that sends 401 and closes the connection as soon as the headers missing auth are received, the process aborts with a broken pipe when (presumably) trying to send the POST body.
session = requests.session(auth=(USER, PASSWORD), verify=False)
resp = session.post('https://foo.com/something')
 --> requests.exceptions.ConnectionError: [Errno 32] Broken pipe

Thanks ABR. You may be better off raising a ticket against requests (https://github.com/kennethreitz/requests).
I'm assuming what you want to happen here is for the session.post() call to return the 401 response without raising an exception. Perfectly reasonable, but to the best of my knowledge the "requests" library isn't in Python's standard library -- and so this is not the place to get it fixed :)

If that's where the bug is. I forgot to mention this issue seems identical to 5542 (http://bugs.python.org/issue5542), but for https. The fix there was in the underlying url/httplib.

Issue5542 was fixed, so if it's the same thing this is also fixed. If it's not the same thing, then python 2.7 is past EOL so please create a new issue if you can reproduce this problem in 3.8+.