[gboudrias]

This was a few years ago, so things may have changed by now. But as they say, once bitten twice shy, and the wisdom of "just cron it" doesn't work with highly experimental tools like LE was for what I estimate to be the majority of its lifetime.

[lvh]

I'm sure there's a way to make your LE experience consistently suck but the way to run caddy for a static website has been the same for about as long as caddy has had support for automatic HTTPS, and that's also true for python-nginx-certbot. But more importantly: we can argue about what it was 4 years ago, or we can just observe that it's really easy now.

[lugg]

A tool not working well or being "experimental" does not dismiss the premise that frequently run automated tools are a better than infrequently run manual tasks when those manual tasks can take down your infrastructure if done improperly, missed or forgotten.

All it being new means is that depending on your risk ratio you need to decide whether updates to the software need testing or whether you need to invest in your own solution - or, how about just wait until it matures and keep the old process until then.

Waiting doesn't invalidate the premise either. It just means you lack the resources to implement it safely and that's ok.