Here's what's going on.   Keep in mind, that post-Trusty this was all
sorted out but backporting the fixes to Trusty will not be easy or
quick.

In Trusty, virtualenv vendorizes pip, which vendorizes requests, which
vendorizes urllib3.  It's the three-layers down vendored urllib3 that
would need to be fixed, but doing that is not easy because of the way
this whole stack interacts.  I think we'd essentially have to backport
everything to either devendorize everything, or build the pip.whl back
up using a patched urllib3 all the way back up to virtualenv.  It's a
massive amount of work.

There's good news though: the virtual environment support built into
Python 3.4 already has all the necessary fixes, so I would highly
recommend using that instead.  First, apt-get install python3.4-venv
(for some reason there's no virtual package python3-venv in Trusty as
there is in Vivid and beyond, but no matter, the python3.4-venv package
does the trick).

Then: `python3 -m venv <dir>`.  Source that venv's activate script, set
your proxies up, and everything should install just fine through squid.

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https://bugs.launchpad.net/bugs/1522500

Title:
  pip in Python 3.4 virtualenvs cannot install using a proxy

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