If I do
# /home/ec2-user/.local/share/letsencrypt/bin/pip install pyOpenSSL==0.14
(based on pip install error on Ubuntu due to pyOpenSSL breaking change · Issue #557 · mitmproxy/mitmproxy · GitHub) then the error changes to
File "/home/ec2-user/.local/share/letsencrypt/bin/letsencrypt", line 7, in <module>
from letsencrypt.cli import main
File "/home/ec2-user/.local/share/letsencrypt/local/lib/python2.7/dist-packages/letsencrypt/cli.py", line 17, in <module>
import OpenSSL
ImportError: No module named OpenSSL
which makes me think something is out of sync.