The 529 will not ask for receipts. You simply request a distribution. The IRS may ask for documentation or you could get audited, so you should have receipts on file. Remember that room and board off campus is capped at the school's cost of attendance or the actual cost. He should keep all the grocery and rent receipts and try not to mix up qualified and unqualified expenses. So get two receipts to separate out the Hot Pockets from the PBR.

You save your receipts.

First year of college, payments went straight from the 529 account to the university (so tuition, room, board and campus book store). Next year, DS will move off campus. How do you make payouts from the account and how do you track "qualified expenses" for room and board? The 529 is fully paid up so I'm trying to capture every qualified expense that I can.