This research addressed two questions: (a) What is the relationship between different patterns of cumulative victimization and psychological distress? And (b) How does the pattern of cumulative victimization and psychological distress influence women's engagement in substance- and sex-related risk behavior? Data were analyzed from interviews with 149 sexually active, crack-using women who completed a follow-up interview after participating in the Kentucky National Institute on Drug Abuse (NIDA) AIDS Cooperative Agreement. Findings from the multivariate analyses indicated that victimization accounted for 5% and 39% of the variance in psychological distress and high-risk behavior, respectively; cumulative victimization and psychological distress accounted for 6% to 11% of the variance in the high-risk behaviors. Results highlight the affects of childhood and adult victimization on psychological distress and the associations between different types of psychological distress and risk behavior.