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At set times now sends at each time you set, even while a window is open. That message costs next to nothing and just doesn't start a new window, so a late window never pushes the rest of your day back.
A set time goes out within 15 minutes of it or not at all (Mac asleep, offline). A failed one is tried again at each check inside those 15 minutes.
Replaces the 3.8.8 rule; nothing waits for an open window to end any more.