I've spent some time as an Army recuiter, perhaps I could help. They will ask questions like these. Have you ever been arrested? Even if the court has expunged your record, you need to come clean. Have you ever taken drugs, if yes, what kind and how long ago? They will drug test. He may have to say if he was in rehab. It depends on how he answers the questions as to what bunny trail they will follow. If he hides anything, it use to be a $10K fine if found out. The best way to find out anything is to ask a different recuiter what the different polices are. You would need to ask, not him. Since the services are drawing down, they can get more picky.