Previous studies have examined media portrayals of total control and institutionalization in prison, and a few studies have considered the connection between media portrayals and depictions of prison escape attempts. The current inquiry seeks to fill this gap in the literature through an autoethnographic case study of the video game The Escapists, in which players assume the role of an inmate whose ultimate goal is to escape prison amid an environment populated by other nonplayer character inmates and guards. In this inquiry, specific attention is paid to the player’s experiences as a subject of control from guards, inmates, surveillance systems, and the prison construct, and how these interactions contextualize and potentially motivate the player to attempt escape. Connections between virtual and real-world escape attempts are discussed. Conceptual and theoretical links between total control and interactive experiences of simulated prison life, as well as implications of this study, are examined.