Raylan's step-mother and aunt, Helen, calls him to tell him Arlo is in jail. Raylan reluctantly goes to Harlan, where Helen tells Raylan he needs to bail out his father. Raylan is wary about getting too involved with his father, who made Raylan live in fear growing up and who was constantly involved in some sort of scheme. Arlo in part blames his behavior on his own father, a religious man who mistreated him. Raylan eventually discovers that Arlo planned to use his own son as a shield from Oxycontin ("hillbilly heroin") runners, whom Arlo had stolen from. Arlo's plan works, as Raylan finds Oxy at the drug runners' house (planted by Helen) and threatens the Oxy runners with jail if he goes after Helen and Arlo again. Raylan doesn't even bother asking Arlo where the stolen Oxy or money is because he knows Arlo will not tell him.

After disrupting an apparent assassination attempt on Ava, Raylan is hellbent on tracking down the responsible parties. However, he soon discovers that Ava may not have been the real target. It is revealed that a hitman employed by the Miami mob wanted Raylan dead. Harlan county Sheriff Hunter Mosley (Brent Sexton) kills the hitman to protect himself and then exposes his true affiliations to Raylan. Ava helps Raylan turn the tables on Mosley and his partner, and Raylan and Ava escape. Boyd is almost killed in prison for talking to Raylan as other inmates view Boyd as a snitch, but Boyd's father Bo saves Boyd.