ABSTRACT. Objective: The current study aims to evaluate individual, relational, and community-level risk and promotive factors for transactional sex involvement among substance-using youth. Method: Youth (ages 14-24 years) presenting for care in an urban emergency department, who reported drug use within the past 6 months, were surveyed as part of a larger study assessing violence. Of the 600 youth enrolled in this study, 350 presented to the emergency department with violent injury. Based on youth presenting with violent injury, a proportionally selected (age and gender) comparison group of youth (n = 250) presenting without violent injury were enrolled. Participants were queried about both risk and promotive factors at the individual, relational, and community levels. Results: Of the sample, 7.3% reported involvement in transactional sex within the past month. Regression analyses indicated that being African American or other race (as compared with White), having more than one sexual partner, depressive symptoms, negative peer infl uence, and substance use treatment utilization were positively associated with transactional sex involvement. Increased school involvement was negatively related to involvement in transactional sex. Conclusions: Drug-using youth who reported recent transactional sex involvement are more likely to experience increased HIV risk, depressive symptoms, and negative peer infl uence and are less likely to experience the promotive factors of school involvement. Future research is needed to better understand the bidirectional relationship between transactional sex involvement and both risk and promotive factors at multiple ecological levels. (J. Stud. Alcohol Drugs, 75, 573-579, 2014)