In this article, the authors (a faculty member and two former students) describe the trajectory that Portland State University has taken over its history to institutionalize transformative learning opportunities within its comprehensive general education program, University Studies. Following a description of the institutional changes that resulted in the community-based, experientially focused courses at the heart of University Studies, the authors explore one particular community partnership involving both a state agency and the national Inside-Out Prison Exchange Program, dedicated to offering transformative experiences in which incarcerated and non-incarcerated students learn together inside correctional facilities. Finally, each author shares a reflective essay about the personal transformation experienced through these Inside-Out courses and the implications of these changes on their lives.