Juveniles serving adult sentences are separated from their families for extensive amounts of time. During incarceration, youths attempt to maintain close relationships with family members, but are faced with challenges. The purpose of this multiple case study was to explore adult incarceration of youthful offenders and its effect on family relationships using Bowen's family systems theory as the theoretical foundation. Three Maryland families who have first-hand experience with the phenomenon were selected to share their stories. Through this study, to the family unit was given voice to assist understanding the experience from multiple perspectives. Interviews were conducted with each family member separately using semistructured protocols, triangulated, coded using open coding strategies, and summarized as case descriptions. Study results led to understanding that families experience different individual and collective adverse effects in relation to the experience. Families shared factors which contributed to breakdowns and resiliency of relationships between family members during and after the experience of incarceration of a youthful offender. Findings of this study support positive social change in human services and public policy. Outcomes of this inquiry support the efforts of advocates in promoting awareness and activism to encourage legislation and funding to serve the needs of this unique population. Findings inform policymakers of the need to promote policies and practices in correctional institutions that address concerns about unsafe and nontherapeutic prison environments, and the need to champion policies and practices that support families in maintaining healthy relationships with incarcerated individuals during and after long periods of incarceration.