Despite decades of critical reframings, policy and practice on prisoner (re)entry often remains situated within a framework of individual responsibility that fails to acknowledge the structural drivers of criminalization. Attending to individual symptoms rather than root social, political and economic causes, such approaches may ultimately reinforce the inequalities and injustices that fuel imprisonment. This article presents a case study of an alternative approach. It examines A New Way of Life Reentry Project, a nonprofit organization in South Los Angeles, California, that offers housing and support to women coming home from prison through a critical and holistic framework-one that attends simultaneously to the physical, mental and social contexts that shape lived experiences before, during and after prison. Drawing from seven years of observation and participation, supplemented by ten in-depth interviews, I argue that a critical, holistic approach can have a significant positive impact for people returning home from prison.