Ask HN: Easiest and least painful way of adding Lets Encrypt?

https://caddyserver.com/ - Caddy works pretty nicely, and you should be able to use it as a reverse proxy in front of apache.

Use this to get exact instructions for your setup:

Personally I use haproxy to forward all LE related requests to certbot in standalone mode.

My email is in my profile if you want to try this and need some help.

You can use the certbot on your local machine and setup a txt record on the DNS of the domain.

Let's Encrypt will verify ownership against that text entry.

Warning for anyone trying to add Lets Encrypt to GCP - absolute nightmare. Would not recommend.

Are you willing to share some details about the challenges you had?

Currently, there isn't any built-in support with AppEngine. The steps you have to go through to ssh in and verify ownership is just a hassle.

kube-lego for kubernetes is just awesome!