I am pretty sure exceed the amount I gave him through his 529.
For tax purposes, the IRS doesn't see "you" as giving him anything through a 529. That 529 is considered it's own "third party source" of income for the student, having nothing to do with you. Just because you may be the custodian of the account doesn't matter either. That 529 money is *not* from you.
Money you give the student out of your pocket is also "third party support". Remember, the parent is not required to provide the student any support what-so-ever. So the IRS considers money you provide/give the student to also be "third party support".
The support requirement is on the student, and only the student.
