Below is a quote from me on this forum from May of last year. I was worrying myself sick over what to do. Guess what? Everything worked out fine. No, he didn't show up in underwear only, but USAFA takes care of everything. Not only will USAFA take care of your DS, but he will have a new family in his fellow Cadets that will take care of him as well.
"I've been on this forum since December of 2016 and have learned a TON of information. I've tried to "soak up" all the advice on what to do for my DS, from buying boots/don't buy boots, what color underwear, do/don't buy socks, computers, which days to visit, what to bring when you come, do/don't accompany to I day, and the list goes on and on.
I've made the decision to send D/S to Colorado Springs June 28th in nothing but his underwear and see what happens!!"