I went to a board my Plebe year. What year is your DS? Also, when you say he did bad on 3 finals, what were his final grades (no need to share here)? But that will have an impact. I am sure each SA has its own unique boards, but they are probably similar nature. The biggest thing is, not the excuses, but what is he doing to fix the issue? Since he had medical issues are these fixed and he is back at it 100%? What were the impacts, such as missed class, etc? If they are not fixed and he will miss more stuff coming up how will he handle this better? If they can directly relate his poor performance to medical, they will be inclined to give him another chance, but what has changed to convince them he can handle things. If they are not fixed, can he take a lighter load next semester and take summer school to catch up. How much extra instruction, outside tutoring, etc has he received? Was he proactive in informing his professors of his issues and missed classes? Was he in touch with them on how to make up lectures, labs, assignments. Did he sleep in class? Was he on time, sat in the front row and participated. These are all things the board will look at and will certainly have feedback from his professors on. I know at USNA professors are required to supply this on students who are UNSAT, I am sure it is at USAFA also. Lots of Cadets and Mids have health issues with surgeries, broken bones, mono, and lots of other fun things that occur to active athletic young men and women who live in close proximity. The SAs work with these folks to get them healthy and back at things. Its all about him being proactive about his situation and showing that this was a one off variation for him and he won't be back in front of them again in May.