In WordPress maintenance automation, you inevitably run into points where you have to decide: keep going, or stop right here? One that took us a long time to get right was this: when a WordPress core update goes wrong and gets rolled back, should the remaining plugin updates continue, or stop?
We eventually switched to the "stop" design, but we started with "keep going" — and several traps surfaced only after running it in production. Here's how the redesign happened.
Three cases to separate
The outcome of a core update, viewed through a rollback lens, falls into three patterns:
Case 1: Core rollback succeeded, site recovered — the site is healthy again after the RB
