It depends. The person who receives the funds (whose social security number (SSN) is on the 1099-Q) has to report the Form 1099-Q on their tax return. If your son's SSN is on the 1099-Q he should file a tax return and report the 1099-Q. If the money went straight to the school, it is treated as if the funds went to the student. Any taxes and penalties due that result from a 529 plan withdrawal overage are calculated on your personal tax return. The information is entered in TurboTax, and TurboTax does the math.