This article offers a descriptive case study of an ongoing community-engaged dialogic learning experience that emphasizes human connection and the evolution of self-narratives within criminal justice contexts. The course in question, Performing History/Autobiography in Progress, is facilitated online as a variation of the Inside-Out Prison Exchange Program. It has been designed to build upon a program where police officers and academy recruits enter a carceral setting to study as peers with incarcerated citizens in a three-credit seminar on criminal justice policy. Primarily, the course focuses on public safety and restorative justice. An important secondary benefit is that the course provides an opportunity for its participants to see the humanity in people previously only recognized as adversaries. Performing History/Autobiography in Progress was designed to follow the Inside-Out course and expands on those gains, using writing and performance to explore further intersections of self and society--the personal and the political--as observed, at least partially, through the prisms of prison and policing. The hope is that this course's arts-based curriculum will push participants to authentically incorporate the voice of "the other" into their own self-narratives so that they might better see all, including themselves, as people with vested interests in their communities and nation. Through participant observation and interviews with the course's instructors, this article shares what has been learned about how notions of self can evolve in a collaborative, humanities-based learning environment.