I think this trophy is more confusing than glitched and it is just a case of not knowing how to do it correctly. However, I have had people tell me that they have done the correct steps and it still hasn’t popped.
The bounties menu in game, or any of the bounty NPC’s are not what this trophy is linked to. You can do as many of these bounties as you like and for the most part they do not count, there is a small chance that some will because once you unlock the correct bounties they will add themselves to the bounties menu if they expire.
You will notice that every safehouse has a computer in that you can interact with and it gives you the areas Liberation Project. This is what is linked to this trophy and the Liberation Project, upon completion, will give you a bounty as a reward. This bounty appears instantly and you have a timer ticking down before it expires. You just need to kill all of these bounties from these Liberation Projects for the trophy. If the timer runs out or if you fail the bounty, it will add itself to the bounties menu and you just need to go and find it and restart it. It should be in the same area as where you got given the project so search for it there. This is good to know if you know you have missed one and need to respawn them, just check the names below for the bosses for bounty and their area;
Meatwagon (Downtown Wast)
12th street (Federal Triangle)
Wolf pack (Judiciary Square)
Jefferson’s legacy (East Mall)
Lafayette’s regulars (Southwest)
Kindled Front (West End)
Peace Movement (Foggy Bottom)
Bully Buzzards (Potomac Park)
Embers Movement (Constitution Hall)
If you are just starting the game it would be a good idea to give this some focus to make sure it is done. Once you visit a safehouse to get the Liberation Project for that area, put some focus into getting it done and unlocking the bounty. Kill the bounty straight away and tick it off this list. If you fail it, you know you need to come back for it. The area where the Campus Settlement is does not have a safehouse, instead you can find the computer hidden in the campus settlement, when you spawn there just walk forward hugging the left and you will notice a path through some crates into a sectioned off area. This is where the computer is for the Liberation Project to this area.