Sociology can be a highly emancipatory discipline, permitting students and researchers to identify and thus alter the structures that contour their lives. Nowhere has this been clearer to me than in teaching sociology to incarcerated students in state prisons. Drawing on nine semesters of teaching experience and a complement of semi-structured interviews, I analyze patterns and challenges that emerge in the teaching and learning of sociology in this environment. I explore how in units of sociology that challenge or denaturalize the social organization of the prison or students' temporary identities, learning is altered and conditioned by their environment. In this sense, my analysis goes beyond other thinking on student engagement with privilege and oppression, showing that the particular social characteristics of a prison have meaningful effects on learning. I conclude by offering thoughts about the power of voice and writing, both public and private, in overcoming some of these obstacles.