So the demoralize action specifically states that it does not stack with itself. But what are the rules for it staking on a previously shaken or frightened creature? And what about the other way around with casting fear (or using a magic item, etc.) on an opponent that has been demoralized?
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Confusing one-directional stacking:
If the target is shaken or frightened or panicked and you demoralize, track the durations separately: The target suffers the stronger effect while both are active, when 1 wears off suffers the remaining effect.
If the target is shaken from demoralize, and is then given the shaken or frightened condition from another source, the new source bumps up to frightened or panicked respectively. Again, track the durations separately, because if the new condition wears off before the demoralize, the target is still shaken.
At least, that's my understanding of it, please someone correct me if I'm wrong here.