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Hi @scoutfinch190

I noticed something here…

Think about the physical proximity of the two guards that would be on either side of him.  Punching their captive in the mouth would make more sense if he was upright and facing them, or pinned to the wall.  At best, a guard might give him a grazing blow down the side of his jaw, but that would be difficult to do with trying to hold him at the same time.  A blow to the back of the head might work, since he would be lower then the two standing guards, but again it would be a cross-body hit, with their free, less dominant arm.  It might be helpful to picture the shot or have two friends help you block it out to see what might work to subdue him.

It is not clear how many guards have Jake, but there would seem to be at least two.  A mouth punch usually clips the nose which would bleed, unless it only impacts the lower jaw, but consider that Jake is just awakening, hanging slack between the two guards with his feet dragging the floor.  To struggle, he would first need to gain his feet and thrust upward, before he could twist and writhe.