Adolescent academic achievement is closely linked to numerous health outcomes. Studies have demonstrated a positive relationship between parental academic monitoring and adolescent academic achievement. Less is known about factors associated with parental academic monitoring, and research is particularly lacking with low-income, African American young adolescents who are at high risk for school disengagement and underachievement. Data were collected from a sample of incoming urban sixth graders using a computer-assisted questionnaire. Data were analyzed as cross-sectional using the responses of 111 African American adolescents, ages 10-14 years. The median responses of adolescents about perceptions of parental academic monitoring were used to classify adolescents into two groups, lower and higher perceived academic monitoring. Logistic regression and stratified analyses determined factors related to higher parental academic monitoring. Adolescents' perceived parental general support (OR: 2.08, CI: 1.29-3.36) and friends' pro-social behavior (OR: 1.54, CI: 1.03-2.30), were significant factors in the multivariate model. Also, adolescents living with one biological parent and with other adults were more likely to report higher parental academic monitoring, compared to adolescents living with one biological parent and no other adults (OR: 3.58, CI: 1.00-12.83). Perceptions of general parental support and peer groups offer insight into why parental academic monitoring allows only some African American urban youth to succeed academically. Parental support provides a context that influences youths' perceptions of their parents' academic monitoring and should be considered in future research. Results identify factors in a high-risk population that may help explain why some urban youth succeed academically while others do not. (Contains 3 tables and 2 figures.)