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The bag under the seat is the only one you are guaranteed to keep. Pack it so that if everything else is gate-checked or delayed, your day still works. A personal item is the small bag that fits under the seat in front of you, and it is the only piece of luggage nobody can take away at the gate. That single fact should decide what goes in it. When the overhead bins fill and your cabin bag is checked at the door, the under-seat bag is what you keep, which makes it the right home for your documents, your medication, your chargers and anything you cannot replace.
