Player found a way to autotrick a target and put a bleed effect with a missed attack. This legal?

[GreyOoze]

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.

[Eric Clingenpeel]

The bleeding shot gets added to effects for debilitating trick. DT specifies that you add the effect on a HIT. So he still has to hit with the trick attack to cause the bleed, it doesn't just go off the trick itself.

SRD Bleeding Shot wrote:

For your debilitating trick, you can afflict your target with an amount of bleed damage equal to your operative level.

SRD Debilitating Trick wrote:

When you hit an enemy with a trick attack, you can make the creature flat-footed or off-target until the beginning of your next turn. You might learn exploits that grant you additional options for your debilitating trick, but you can select only one option each time you hit with a trick attack.

[HammerJack]

Right. Applying debilitating effects from a missed trick attack is not, and never has been, a thing.

[GreyOoze]

Ah ok this makes sense.

Yeah I guess I got confused with the relationship between trick attack, debilitating trick and bleeding shot.

I pointed it out to him during the game and he said the bluff roll was to check if the debilitating shot was successful or not. To speed up the game I kinda let is slide since things were running late.

Thanks for the info!