Background/Context: Prison settings present some of the deepest democratic contradictions in the United States. Purpose/Objective: In this study, we investigate how and what teacher education programs can learn from and support teaching practices in prison settings and pre-K-12 contexts. Population/Participants: This study draws from interview data collected from two experienced directors of prison education programs in the United States. Research Design: This study employs in-depth qualitative interviews. Data Collection: Participants were asked questions related to ideals and mindsets they have observed as most effective for teachers to adopt when working in prison settings. Findings/Results: Analytic induction of interviews reveals both similarities and differences between "free world" and prison educational settings. Such findings provide nuanced understandings of the types of knowledge, understanding, and skills teacher education programs might support in prison settings as well as teaching experiences within prison settings from which teacher educators could learn. Conclusions/Recommendations: Teachers in prison settings tend to have rich content knowledge but not robust pedagogical knowledge and skill. Teacher education programs have a chance to not only support teachers in prison education as they build pedagogical knowledge and skills but also be front and center in the fight to dismantle an unjust carceral system.