After the June, 2015 prison break from Clinton Correctional Facility in Dannemora, NY, Joyce "Tilly" Mitchell is questioned about her involvement with the two men. Months earlier, Tilly enjoys her job at the prison tailor shop, balancing the temptations of David Sweat, a younger inmate, and her obligations to her husband, Lyle. Richard Matt, an inmate with an artistic talent, supplies oil paintings to guards in exchange for special treatment. Ultimately his attentions turn to Tilly.

Matt and Sweat run into walls and other obstacles as they search for a way out, but the power of positive thinking helps keep them on track. Tilly begins to feel guilty about her mounting indiscretions, but she has a funny way of showing it.