Originally Posted by Rascalov
I think this might be missable. I killed the first guy and the second guy hasn't shown up. I might have killed him as well without realising - not sure. If you kill any of them does that screw up the achievement?
The achievement is missable to my knowledge but it's from killing all of them and not saving/handing over at least one for the achievement.
I killed bounties #2/3 but I still got an email from Maude for #4. So killing them should not void you receiving the missions, only not handing a bounty over alive will.