I dealt mainly with soldiers who had an operational stress injury or mental health concerns. Most of the drugs would be in the range of antidepressants, anti-anxiety pills, and so on and so forth, and that was a big concern.
The other big concern was with starting your whole prescription life again once you get out, because the DND ones literally stop. If you need meds for another month, you're going to have to get at that pretty quickly. You have to get in to see a doctor, and the doctor is just going to take what he knows and work through it; he's not just going to blindly sign off on the prescriptions you say you were getting.
Some of the medications are life-saving too, so that's a big concern with regard to that transition.