I was trying to run ansible over a debian slim docker image and I got this error, which was rather cryptic.  There wasn’t any particularly good information on google for fixing it either.

ContextualVersionConflict: (cryptography 1.7.1 (/usr/lib/python2.7/dist-packages), Requirement.parse(‘cryptography>=2.5’), set([‘paramiko’]))
ERROR! Unexpected Exception, this is probably a bug: (cryptography 1.7.1 (/usr/lib/python2.7/dist-packages), Requirement.parse(‘cryptography>=2.5’), set([‘paramiko’]))
the full traceback was:

Traceback (most recent call last):
File “/usr/local/bin/ansible-playbook”, line 97, in <module>
mycli = getattr(__import__(“ansible.cli.%s” % sub, fromlist=[myclass])…

In my case, running this before my ansible install resolved the issue.  It just forces an upgrade to a newer version which ansible is okay with.  Of course, if you were dependent on the lesser version this may not be an option.

pip install –force-reinstall cryptography==2.7