The present study’s goal is to illuminate how media-generated popular cultural understanding of prison impacts the educational, therapeutic, and administrative work non-uniformed staff engage in with people who are incarcerated. Understanding these dynamics is vital because non-uniformed prison staff play instrumental roles in supporting people who are incarcerated with making the transition to future community members. We argue that non-uniformed staff rarely feature in media accounts of prison, yet these popular cultural representations of prison nonetheless shape both the work they are able to carry out in prison and their perspectives their work. Uniting and building on literature in cultural criminology, prison social climate, and transdisciplinary work on courtesy stigma, this article unfolds in two parts. First, we explore how non-uniformed staff conceptualize and interpret the impact of media representations of prison on their everyday work. Second, we examine how nonuniformed staff respond to the political will wielded by a media-educated voting public in determining their work’s scope in prison.