Many educators view the process of education as transformative. This transformation is important in all classrooms, but it takes on added importance in prison classrooms. The education that inmates receive in prison can mean the difference between the doorway of freedom with a productive future and the revolving door of recidivism. For many prison educators, this transformative and liberating education process takes the form of democratic citizenship education. This article on interviews with five instructors from Ball State University's Department of Extended Education as well as the teaching experiences of the author. While the subjects taught by these individuals range from computer science to English to anthropology, their approaches and views of transformation through democratic citizen education were very similar. By addressing the societal inequality that is reflected in prisons, these educators are themselves acting as engaged citizens. They show the twin ideas of awareness and action that are required of all citizens. These educators promote citizenship education by creating safe democratic spaces in their classrooms, which depend upon power sharing with their students. Finally, they seek to transform their students into active, aware, and engaged citizens by fostering critical thinking skills, encouraging debate, and applying course lessons to the lives of their students.