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 has an idea to get out of Dannemora, but Sweat is not interested in taking the risk. Matt begins to help Tilly with an inmate she doesn't get along with in the shop, while Sweat comes to miss the freedoms that come with Matt's protection.

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.

Excited by the possibility of a new life, Tilly tries her best to avoid Lyle, who is planning something special for their anniversary. Sweat makes progress on the escape route, but feels like he’s doing all the work. Matt likes the arrangement just fine.

On the day of the escape, Matt and Sweat know the smallest mistake can derail their whole plan. But when a stern corrections officer takes over the post in the tailor shop and fellow inmate Murder gets out of the Special Housing Unit, Matt seems attracted to the danger. Tilly and Lyle have a fateful dinner at an all-you-can-eat Chinese restaurant.

In a deep dive into the minds of these individuals, we finally see what Matt and Sweat are capable of outside the prison walls. Tilly’s natural instincts aren’t much better.