Raylan visits Boyd in the prison hospital to check on him, and transport Crowe to prison. Meanwhile, during a 'prison band' performance, convict Douglas Cooper and a fellow inmate escape. After Art Mullen asks Raylan to return to investigate, Raylan makes a stop at a gas station. Unbeknownst to Raylan, the convicts have set a trap, and Cooper makes off with Raylan's guns, car and hat. After learning that Cooper only had three months left on his sentence, Raylan and marshal Gutterson make a trip to Cooper's ex-wife, Shirley. Cooper then visits after and makes a deal with Shirley and Dupree, Shirley's 'cousin'. They are looking for money Cooper hid in the flooring of development housing during construction. After Ava makes a house call to Raylan, he discovers a hunch as to the location of the money. Cooper, however, screwed up the location. After Dupree shoots Cooper, they find the right house, whose occupants have spent it all. A hostage situation ensues after Cooper helps Raylan find the right house, and Shirley helps Raylan by allowing Gutterson to snipe Dupree, citing that it 'wasn't right' to shoot Cooper. The episode ends with a nice conversation between Cooper and Raylan as they once again leave the prison.