This article shares first-hand experiences and reflections of individuals who participated in a community writing project between university students and women incarcerated and participating in a therapeutic community (TC) in Washington state. Together, the students and women explored the causes, impacts, and treatment of addiction and designed an online platform to share their writing, artwork, and research about the issues that have shaped their lives. Through the reflections of the participants and sponsors, common themes—such as navigating dynamics of stereotypes and authority, reframing narratives of transformation, and building connections through both empathy and alterity—emerge. This article explores the opportunities and complexities that emerge when unincarcerated university students and incarcerated writers collaborate to create a project to help reshape rhetorics not only about addiction and recovery within a carceral setting but also about the potential of a liberatory experience within such a setting.