I’m the one who asked about supervision at the beginning of this thread. As the father of teenaged sons, I can emphasize with your comment about a jail like setting, I can’t sympathize with you though 🙂
Back to the subject at hand. Could you elaborate on why and when a bachur would have the need to hitch a ride somewhere? Is it to seder, davening or a meal? Is it to a simcha? Shopping? How much time (or alternately how often) do bachurim have to engage in this activity? When these bachurim are hitching, is the yeshiva aware of where they are, why they are not in the yeshiva and when they are expected back?