Don't forget this[1] gem which is my favorite way to use letsencrypt. It will let me run it by cron (or periodic on FreeBSD) plus I can have my own post-run script that takes my certificates and keys and puts them in the format I need for Hitch (SSL termination for Varnish), push those changes, restart the service _inside_ a FreeBSD jail automatically.

It's advanced setups like this where LetsEncrypt fails out of the box, but it's nice we have tools like this at our disposal now.

[1] https://github.com/lukas2511/letsencrypt.sh