This project examined the effectiveness of a transitional program in breaking the cycle of homelessness. Within a community-based research approach, the authors conducted a case study to describe the program and participants within a context in which housing is largely unavailable and unaffordable. Although most participants successfully transitioned to housing few transitioned from homelessness to economic self-sufficiency in market housing and participants remained in poverty. Evaluations of housing programs can “blame the victim” or “blame the program” when measures of success are not achieved. Interventions to address homelessness require attention to the system-level forces that create and sustain poverty and inequities.