I think this is fixed by the following commit to python-cryptography.

commit 9837cb15b84fea92ffce3306d14160a8c11b1c65
Author: Paul Kehrer <paul.l.keh...@gmail.com>
Date:   Mon Aug 24 08:00:10 2015 -0500

    make engine addition idempotent

    Threading issues keep cropping up. ENGINE_add already
    acquires a lock at the C layer via CRYPTO_w_lock (provided you
    have registered the locking callbacks) so let's try to use that.

    As part of this we'll try to init the openssl locks, but of course
    there's potentially a race there as well. Clearly this isn't the real
    fix but it might improve the situation while we try to determine what to
    do.

** Changed in: python-cryptography (Ubuntu)
       Status: New => Triaged

** Changed in: python-cryptography (Ubuntu)
   Importance: Undecided => High

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https://bugs.launchpad.net/bugs/1601986

Title:
  RuntimeError: osrandom engine already registered

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