Comment by tptacek
If you're using LetsEncrypt without automation you're doing it wrong, and the reason that the WebPKI is so hacky is that it was insulated from basic computer science for 2 decades and run by enterprise software companies.
You have to automate certificates. You can't do these by hand anymore. Certificate lifetimes are going to get inexorably shorter.
Wow, I came back to this thread and it unexpectedly blew up. Looks like my experience is not normal and L.E. is not flaky for anyone else on HN. Who knew my simple 6 line shell script has been buggy for a decade.
I guess if you zoom out, one of the things I bristle with is LetsEncrypt's opinionated way of changing people's behavior. The short certificates were a deliberate decision, done to "get users to do X." They were pretty transparent about it. In my view, computers should do what users want them to do, not what developers want users to do. We've got enough software out there with notifications and consent dialogs begging users to do this and that, and this just adds to the problem.
I get that the software is free (which was a revolution in the PKI world at the time), but the short lifespan seems to be either a behavior modification experiment OR an annoyance to get people to fork over money for the better (better for users, not necessarily for security), longer-lived products.