We investigated determinants of parental monitoring and the association between parental monitoring and preadolescent sexual risk situations among low-income, African American families living in urban public housing. Preadolescents and their parents or caregivers who participated in a longitudinal study of familial and contextual influences on HIV/AIDS risk provided data on parental monitoring and preadolescent sexual risk situations. Data were also collected on parent risk factors (psychological distress, maternal age at first childbirth); preadolescent risk factors (responsiveness to parents, peer pressure) and contextual factors (parenting help, household type, friendship, partner presence, and perception of religious guidance) that were hypothesized to predict parental monitoring levels. Results showed that greater parental monitoring predicted less sexual risk situations. Further, instrumental and emotional supports were both significant predictors of parental monitoring, but parent and preadolescent risk factors were not strongly associated with parental monitoring. These results were similar for male and female preadolescent youth. Our findings suggest that preventive interventions to reduce sexual risk situations for urban, African American youth should consider parental monitoring. In addition, contextual factors such as strong parental friendship networks and instrumental help may enable parents to provide closer monitoring of youth.