I did an upgrade of my Ubuntu Bionic server and certbot fails now with:
certbot
An unexpected error occurred:
ContextualVersionConflict: (cryptography 2.1.4 (/usr/lib/python2.7/dist-packages), Requirement.parse('cryptography>=2.3'), set(['PyOpenSSL']))
I can't seem to fix it no matter what I do.
It looks like you need to updated cryptograpy package
Also it looks like current version is 2.7