Our research explored the experiences of educators who teach in a gender-responsive program for women in a jail. We interrogated how educators fostered empowerment in their classes, what their motivations were for teaching in the program, and the tensions that existed for them when using emancipatory teaching practices in jail. Findings indicate that educators used Freirean concepts to foster empowerment, were motivated to share their knowledge, were motivated to counter dehumanization, and recognized their commonalities and privilege. Trust and agency created tensions while using an emancipatory pedagogy at a jail. Findings have implications for educators teaching marginalized populations.