The requirement on the withdrawals from 529 plans is that it is used for college tuition. The brokerage will issue a Form 1099Q and you need to be able to show that it was used for the tuition. In the filing for 2023, you will be asked if you paid tuition in the year prior. This will match to the issued Form 1099Q.
This is also a good plan:
"Would I be better off paying the tuition from my bank account by 12/1/22 and getting reimbursed from my 529 1/1/23 or later?"
It actually keeps the whole transaction clean and simple.
By the way, if you do it in 2022, have the check sent directly to the college or university.
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