So, if you are wondering why you can’t remotely decrypt your server after a reboot, you might check your VPN…
Ours was running in an LXC container…on the very computer we were trying to reboot. SO of course, the container WAS NOT RUNNING. After some panic when SSH did not respond, we found that ALL web services did not respond. We actually really liked that! It was only then that we figured out or dumb mistake…
“Pro Tip” – Disconnect the non-functioning VPN before you SSH to the encrypted server. It’s a lot less stressful than trying to do it the other way round. 😐