The xp evaluator was skipping silently whenever `advancement_ready` was already set, which meant once a level-up was queued the DM had to remember to act on it on their own. In practice that turned out to be easy to lose track of — the flag would just sit there. Now when the evaluator wakes up and finds a pending advancement, instead of doing nothing it appends a short reminder to the DM notification channel and returns without spending tokens on a Claude call. The repetition itself (one reminder per evaluator wake) creates the urgency, without needing a counter or escalation state. If that turns out to be too quiet we can layer on stronger language after N reminders later. Co-Authored-By: Claude Opus 4.6 (1M context) <noreply@anthropic.com>