I discovered the root cause of the issue by comparing the output of `pip freeze` on both servers.
Apparently on the upgraded server cryptography-1.9 was installed in `/usr/local/python2.7/dist-packages`, while overriding python- cryptography package. Running `sudo pip uninstall cryptography` resolves the issue. -- You received this bug notification because you are a member of Ubuntu Bugs, which is subscribed to Ubuntu. https://bugs.launchpad.net/bugs/1733311 Title: pip crashes at startup importing from OpenSSL To manage notifications about this bug go to: https://bugs.launchpad.net/ubuntu/+source/pyopenssl/+bug/1733311/+subscriptions -- ubuntu-bugs mailing list ubuntu-bugs@lists.ubuntu.com https://lists.ubuntu.com/mailman/listinfo/ubuntu-bugs
