Expiry is the failure mode, not misconfiguration
Certificates are free and issuance is automated, so the interesting risk is not getting one — it is renewal quietly breaking and nobody noticing until the browser warning appears.
The pattern is consistent: automated renewal is configured, something changes underneath it — a plugin, an authenticator, a DNS provider — and the renewal fails silently every night for weeks. The site keeps working, because the existing certificate is still valid, right up until the day it is not.
Two defences. Monitor days-to-expiry as a metric rather than waiting for the failure, and periodically run the renewal in dry-run mode, which catches a broken configuration while there is still time to fix it. A wildcard certificate needs particular care: it can only be issued through a DNS challenge, so a renewal configured for an HTTP challenge will fail every time while appearing to be set up correctly.