Prior research has consistently found disproportionate rates of traumatization and psychopathology in criminal justice-involved women. The current study aimed to characterize rates of traumatization, psychopathology, and diagnostic comorbidity in women involved with the justice system. Furthermore, this study examined the role of posttraumatic stress symptoms in the association between traumatic events and levels of self-esteem. Participants were 185 women from the Chicagoland area with current or previous (past 2 years) involvement with the criminal justice system. Results confirmed disproportionate rates of trauma experiences and psychopathology in this population, and logistic regression analyses indicated that rates of traumatization predicted diagnostic comorbidity. Analyses indicated an indirect effect of posttraumatic stress in the association between traumatic experiences and self-esteem. Findings highlight the importance of assessing and targeting both trauma experiences and posttraumatic stress in justice-involved women to optimize prevention and intervention efforts.