Substance abuse is a major contributing factor to women being incarcerated in the United States, and substance abuse is a critical factor in the high recidivism rates of women offenders (50–70% within one year). Understanding factors that enhance and deter women from retention in substance abuse treatment will facilitate tailored interventions to improve treatment outcomes. This prospective study examined the relationship of substance use characteristics, childhood trauma, current trauma-related symptoms, motivation to treatment, and socio-demographic characteristics, in predicting the retention of women offenders in an urban, residential substance abuse program as they re-enter the community from incarceration. All women were interviewed within the first week of admission to the residential program using the following measures: the Addiction Severity Index (ASI), the Childhood Trauma Questionnaire (CTQ), and the Trauma Symptom Inventory (TSI), and socio-demographic characteristics. Length of stay was tracked for all study participants (n= 105). Using multiple regression analysis, substance use characteristics did not predict retention. Age, current use of prescribed pain medication, sexual concerns, employment problems, and importance of drug treatment were significant predictors. Specifically, women remained in treatment longer if they were older, were not taking any prescription pain medication, reported concerns about employment, reported concerns about sexual problems, and reported lower importance of drug treatment, yet higher personal commitment to recovery. Higher scores for childhood emotional trauma, emotional neglect, and physical neglect were correlated with retention, but not statistically significant. These findings suggest the need to tailor individualized treatment to address the medical, employment, sexual and interpersonal relationships, and emotional trauma needs in this vulnerable population of women.