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It sounds like there's something wrong with the keyboard, e.g. it is not holding a charge.
Normally (with sufficient energy stored in battery) tapping a key (say, Shift) will restore previous connection, you don't need to re-pair. And it'll have a timeout more like 15-30 minutes of inactivity.
It's perfectly normal to have the keyboard disconnect after some timeout to conserve battery but not normal to have to go to Settings to do anything to restore.
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