
I don't know the exact rules, but I'm pretty sure it has to do with whether the inscription in the box matches the location it was mailed from. It looks like it was mailed from Pheonix.
Either way, they aren't actually paying for the postage twice. When there isn't a stamp, it gets tallied up by permit number. Since there is a spray-on cancel, that means the machinery recognized there was a stamp on it.