This study compares the characteristics of out-of-treatment, homeless, crack-using African-American women with those who are not homeless to determine what risks and protective factors differentiate the two groups. From 1999 to 2001, 683 out-of-treatment, African-American crack-using women (of whom 219 were categorized as homeless) were interviewed and serologically tested. Risk factors that were examined include adverse childhood experiences, psychological distress, physical health, violence and victimization, drug use, and risky sex behaviors. Protective factors that were examined include marital status, education, public assistance, and the responsibility of caring for children. Overall, both groups of women started crack use in their mid-twenties and started drug use with alcohol in their teenage years, though differed significantly on each risk factor examined. Logistic regression analysis found that variables associated with increased odds of being homeless are physical abuse before age 18, crack runs greater than 24 hours, income less than dollars 500 in the last 30 days, depression, and current cigarette smoking. Protective factors found are marital status, living with children under 18, having had a physical in the past year, and receiving money from welfare in the last 30 days. Being sexually assaulted in the past 90 days was marginally associated with homelessness in the model. These findings, specific to crack-using African-American women, suggest that not only do these women overall report painful histories and currently stressful lives, but homeless women are more likely than women who are not homeless to have experienced childhood abuse and are more involved with drug use. Interventions designed for these women need to consider gender, cultural, and contextual issues that not only incorporate aspects of risk reduction related to violence, alcohol use, and comorbid conditions, but also linkages that will address housing issues, education, and skills for independence.