Scholars have studied incarceration among women in the United States of America for more than a decade, but few studies have explored the influence of repeated incarcerations among African American women and their family relationships. The research question for this study examined how African American women describe the effects of multiple incarcerations on family trust relationships and their ability to reintegrate into the family system and society. This multiple case study was conducted in Chicago, Illinois, and drew a sample of 4 African American women released from prison with histories of multiple incarcerations. The study explored their perspectives through a series of semistructured, in-depth interviews. Data consisted of narrative interview transcripts and artifacts collected and analyzed using a framework of feminist theory and critical criminology. Findings from the analysis indicated these African American women experienced profound and long-term devastation to relationships with family and friends following periods of multiple incarcerations. Repeated periods of imprisonment negatively altered their perceptions of themselves and reduced their social engagement with others. Results of repeated incarcerations included (a) broken trust with loved ones; (b) resentment, anger, and blame; and (c) permanent damage to social and family networks. This study contributes to social change by increasing understanding of the repercussions and effects of multiple incarcerations on African American women and family continuity, and the study offers insight into guiding program development to help families rebuild and stabilize.