Caddy can do both. If you’re using a wildcard already, stick with it. In fact, I’d say it’s more prudent to use wildcards (with DNS challenges) than http challenges.Then you aren’t listing all of your domains in letsencrypt’s public database for everyone to see. Nobody needs to know you’ve got a site called bulwarksdirtyunderpants.bulwark.ninja

Good write up. Thanks for the good lessons learned section.

Tmux is your friend for running stuff disconnected. And I agree with the other post about btrfs send/receive.