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Prisoners can break windows, but they cannot escape through them even if they do.
I've attempted to do both in escape mode myself and windows are little more than just a decoration.
I theorize that maybe - just maybe - if you drop contraband right up against a wall it might glitch through a wall in a million to one freak accident, but I've never seen it happen despite my best efforts to do it deliberately.
As for AI prisoners, if they could escape or trade through windows, I would have seen them try at some point as they are very determined when it comes to contraband and escapes, so safe to assume they simply can't.