One of my players managed to stack some stuff and I'm wondering if I am doing something wrong here. So basically he has Specialization Skill Mastery with bluff and bleeding shot.
What he does is he takes a 10 when making a trick attack. This allows him to autotrick anything that is CR 12 and below. (I don't remember what his bluff is)
He also picked up bleeding shot recently.
Last game they were fighting a young red dragon. The player attempts to do the trick attack and since the cr is 9, he auto tricks it. When he roles to hit, he missed the dragon. What I'm trying to figure out is does the bleeding shot kick in even if he missed?
If it is, there is something wrong here. He basically tricked a dragon to bump it's nose and take 8 points of bleed damage every round till the dragon gets medical attention.