What does 'the first matching window wins' mean in a schedule?
If a moment falls inside more than one window, Skie applies the first one in the list that matches. Windows are checked from the top, and the first match decides the app set. Put specific windows, such as exam time, above broad ones, such as general school hours.
Overlaps happen. Imagine a broad 'School hours' window from 8 am to 3 pm, and a narrower 'Maths test' window from 10 am to 11 am. At 10:15 both match. Skie goes down the list and stops at the first window that matches.
That means order is a tool. If the test window is above the general window, the test window wins at 10:15 and the device shows only the test app set. If it is below, the general window wins and the test apps never apply. The fix is not a special setting, just the order of the list.
Use the rule on purpose. Place exceptions first and the everyday rules after them. An exam window above the lessons window, a holiday window above a weekday window, a night window above a catch-all. Windows that do not overlap are unaffected, so this is only something to think about when you want one to override another.
For a one-off lesson where a class needs an extra app, you do not have to fiddle with order. Skie has an option for extra apps for one lesson, applied to a whole class in one step. A practical tip is to read your schedule from top to bottom aloud, asking at each line 'does this ever swallow the one below it?', and to check the result on a pilot tablet at a time when two windows overlap.