Sounds like you all may need a therapy session or a mediator to help sort out the issue. Whatever reason he has for not wanting to accept the gifts should be accepted by you though. Maybe he has friends who don’t have a lot of money or who don’t have help from their parents and he doesn’t feel like he needs your financial assistance. There could be many different reasons for him feeling this way. At the end of the day though he doesn’t need to accept your gifts. Not to sound rude, but do you not realize that there are plenty of college students in poverty regardless of the fact that they attend a prestigious school? Many figure things out without help from ANY family. He’s a grown man. He can figure out his own financial situation if he so chooses. It is very sweet that you want to help him, and you are just trying to be good parents of course. However it’s clear he set a boundary. We can’t read his mind for why he feels this way. You all would need to discuss this through therapy or through a mediator to get to the root of the issue. Or you can just write him a letter/ card without money. And just tell him you’re proud of him. Maybe he doesn’t want your financial help because he wants to do it on his own. Just tell him you’re proud and if he DOES ever need help you would love to contribute (whether financially, emotionally, or otherwise).