It seems like the culprit is your Now() in your button
Now() always output a Date/Time value (the precision here is to the seconds).
In your button, you use it to create an apparent date in your table [Issue History].
But if you display Now() in a Date field, the time part will still be there, hidden behind the scene.
So, in your table [Aggregated Data], you’re not exactly comparing a date to a date but a date/time (with a certain set of hours, minutes and seconds behind the scene) to another date/time (where the time part would be set to midnight, as it’s the default time value for a date) both displayed as a dates… which is only corrected when you edit the field … or vice-versa .
My point here being that there seem to be a mismatch between the values in the Date field in your table [Issue History] and the Date field in your table [Aggregated Data] which most likely comes from Now()
Depending on how important Now() is in your setup, you could use Now("day") (which is the equivalent to Today()… I’ve talked a little bit about this recently, in this topic )
… or in your Filter() in the duration field Reported, you could round your CurrentValue.date to the day unit using DateTimeTruncate() .