The quest is started by the player encountering the dead body of a Morag Tong assassin. Upon searching the corpse, they discover a note describing the assassin’s task to kill a former slaver named Endyrn Dredayn.
From here the player is prompted by their quest marker to seek out Dredayn's estate. As soon as the player opens the door to enter the estate, they are forcefully greeted by Dirk, who questions their arrival. The player's actions may result in Dirk attacking them. This leads to combat with both Dirk and Dredayn.
If the player chooses to be civil with Dirk, he leads them to Dredayn, who thanks the player for warning him about the assassin, and proposes that the player assists him in cleaning up his past once and for all. This request manifests itself in the form of three assassination jobs. Each is a former business partner of Dredayn's.
After killing a target, they player may return to Dredayn for their reward, and are then given information concerning the next target.
The quest can be resolved in two ways. First, the player can kill all three of Dredayn's targets, and complete the job. Alternatively, they can decide to kill Dredayn and collect the bounty on his head.
The final target, Waldran, asks the player to kill Dredayn for them. The actual gold reward for killing Dredayn can be found afterward at a dead drop location.