Yeah... so.... he's going to rage at you when you don't give him the money on time because he hasn't met your requirements. Be prepared for that, it's going to be nasty! Like... probably nastier than anything you've ever experienced with him before, because that is a legitimate high-stress situation for him. And, from the sounds of it, he will not accept that that's his OWN fault that he's in that mess.

Also - don't be surprised if the psychiatrist comes back and says there's nothing wrong with him. Your son has likely lied and acted to the best of his ability. I would suggest - IF he has been successful in convincing the psychiatrist of this, that you only give him as much for the base tuition for the first semester/term. Give the BARE minimum and tell him he'll get more when he continues going. Do NOT give him any extra - don't cover his books, don't cover his expenses. Just the base tuition costs so that he can attend class.

Make him go back to the psychiatrist anyway, even if he's managed to con him over. AND. If the pyschiatrist has seen through it, still only give him that bare minimum to make sure that he goes to more appointments. Pay that base tuition. If you were going to cover other costs? Do not give him the money for them until after he's gone to more appointments - because seriously, he can go without the textbooks for a while. Most students don't even look at them And as the poster above said - don't give him the cash. Go in with him to pay for things.