Can't install let's encrypt: «undefined symbol: OPENSSL_sk_num»

hi @SilentImp

Are you open to use other clients?

There are a couple of good Bash Clients (GetSSL and which do not have python dependencies and have a high level of automation

The reason why I mention this is that by the looks of it your servers python configs need a bit of work and there is a benefit vs reward analysis which can be done here

If you want to carry on fixing python in the virtual environment then that’s ok as well.

I believe your issue is that you do not have the intermediate required for downloading packages over SSL from PYPI.

Have a look at this article on how I built certbot on windows: Running Certbot on Windows - Phase 1

A lot of the steps are not relevant to your setup as you are on linux but there is a note about missing intermediate certificate