Trellis Dev Server - vagrant up stuck - libssl1.1:amd64/ Python error

Ran into the same issue. Seems to be a known issue. https://bugs.launchpad.net/ubuntu/+source/openssl/+bug/1832919

What I did is follow the steps in comment #10.

Get into the box with vagrant ssh and then run:

sudo dpkg-reconfigure libc6
sudo dpkg --configure libssl1.1
sudo dpkg-reconfigure libssl1.1

Then run vagrant provision again and it will finish the process.

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