Once a year for a number of years we would have a small total outage as our Ops team forgot to renew our wildcard certificate. Like clockwork.
It's been a couple of years now so they must have set better reminders for themselves.
I have tried several times to convince them of the joys of ACME, but they're insistent that a Let's Encrypt certificate "looks unprofessional". More professional than a down application in my opinion at least. It's not the early 2000s anymore, no one's looking at your certificate.