The overrepresentation of Native Hawaiians in Hawai‘i’s criminal justice system is among the most stunning of ethnic/racial disparities in the state. To describe the human impact of Native Hawaiians involvement in the criminal justice system, the authors interviewed persons with criminal histories, correctional officials, social workers, and others. Findings reveal systemic challenges to prison exit and community reentry, including lack of services stipulated for release and upon reentry, marginalization associated with cultural trauma, resource deficits, and stigma. The National Association of Social Workers encourages social work leadership in policy formulation and service development. Suggested are strategies for influencing community attitudes, program access, and culturally-grounded services.