"I requested a distribution from his 529 on 12/30/2019, and paid his college on 1/5/2020". When did the 529 plan send the money (when did it leave your account) ad when did you receive it?
You basically have the same situation, as with the other distribution. Claim what you need to claim and hope you can explain it to the IRS, if they contact you because the paper work doesn't match.
