[TedDoesntTalk]

HTTPS is indeed broken when viewing it from a site reliability perspective. Anyone who has maintained more than a handful of domains simultaneously will agree (personally I’ve managed hundreds, each with their own certificate … it’s an awful experience).

[middleclick]

Awful in what sense though? I also maintain many domains and have not touched them in years since their initial setup, with LetsEncrypt (and the Certbot renewal timer).

[verdverm]

I've had several sites with HTTPS work for many years now with zero effort or SRE time. Let's Encrypt via certbot handles it all for me

[baisq]

Lucky you. I’ve had multiple problems like rate limits, cron not firing, let’s encrypt servers not being able to see challenge files because of obscure rewrite rules… it’s far from flawless

[verdverm]

I don't think of it as luck, more about good devops practices and not letting tech debt creep