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For Engagements, the cadences are "regular", that is, they are on a set schedule for Mondays at 3pm, etc.
So there is NEVER a reason to use a trigger unless you happen to need an immediate emails send before the Engagement's emails. Thus, you should setup a batch campaign to capture everyone who meets the Entry criteria that day (or week). This will solve your problem by picking up those who qualify, when they qualify and avoid the point in time trigger issue.