The present analysis was guided by a gendered pathways-based theoretical model and examined relationships between childhood victimization and current attachment, psychological distress, and substance use among 406 women with histories of victimization who were on probation and parole in an urban Kentucky county. Structural equation modeling examined relationships among childhood victimization, attachment, psychological distress, and substance use. Additionally, we examined the mediational role that attachment plays in relationships between childhood victimization and both psychological distress and substance use. The data fit the models properly. Psychological distress was significantly predicted by childhood victimization, and adult attachment partially mediated this relationship. Childhood victimization did not significantly predict substance use; however, attachment did. The findings suggest that attachment may be an important factor to further understand and address in relation to psychological distress and substance use among women with histories of victimization who are involved in the criminal justice system.