I have suspicions about what could be the cause - shifts in privileges, user-amnesia, or maybe the automation had no events in the last 2 weeks and I just need to provide some reassurance that everything is working as expected. Odds are I'll have to reconfigure his dashboard or "shudder" add an email to the process. Whatever, he'll probably message me in another 3 months with a new observation.
Somewhat unrelated to this most recent feedback, I think tech has built great frameworks and underlying technology, but few people are mindful of the "final mile" that puts things in front of people's faces. Tailor-made AI solutions feel like the antithesis of this challenge to me; what has worked is withered technology like the interfaces that people trust.