The manual process was annoying but it wasn't complicated.

You knew exactly when it was going to fail and you could put it on your calendar to schedule the work, which consisted of an email validation process and running a command to issue the certificate request from your generated key.

The only moving part was the issued certificate, which you copied and pasted over and reloaded the server. There are a lot less things to go wrong on this process, which at one point I could do once every two years, than in a really complicated automated background task that has to happen within 15 days.

I love short duration automated free certs, but I think we really need to have a conversation about how short we can make them before we make it so humans no longer have the time required to fix problems anymore.