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Running certbot-auto gives this output:
Error: couldn't get currently installed version for ...
File "/opt/eff.org/certbot/venv/local/lib/python2.7/site-packages/cryptography/hazmat/bindings/openssl/binding.py", line 140, in init_static_locks import("_ssl") ImportError: No module named _ssl
This occurred after a dist-upgrade from Debian 7 -> Debian 8
certbot-auto uses its own installed virtual environment, including its own build of python. This was (naturally) not updated in the dist-upgrade to Jessie. certbot-auto did not detect that it needed a rebuild, thinking that all the dependencies were satisfactorily already installed.
So the fix was:
rm -rf /opt/eff.org
/usr/local/bin/certbot-auto
which then downloaded and rebuilt all that was needed.
I also upgraded a system from Debian 7 to Debian 8, but found no file with the name "certbot-auto". So I renamed /opt/eff.org to /opt/eff.org.old and started letsencrypt-auto which downloaded the necessary files.
letsencrypt-auto is the really old name for certbot-auto.
Dec 2, 2018 at 15:48