Yes, the behavior you’re describing is expected with the current implementation. RefreshMySegments, RefreshPromotions, and login will not attach the promotion to users who are already in the segment, because the system is designed to only grant automated promotions when the user enters the segment (i.e., when it shows up in enteredIds). The fact that Reset Segments or Re‑evaluate All Segments fixes it is also expected, because those actions force the user back through the segment‑entry logic.
We’re working on a fix to make this smoother. The practical effect going forward will be that, when a new automated promotion is created or attached to an existing segment, the next segment refresh will automatically apply it to all currently‑eligible users in the background, without you needing to reset or re‑evaluate segments manually. This should make the behavior more predictable, especially when you have a large number of existing users already in that segment.