Parents raising youth in high-risk communities at times rely on active, involved monitoring strategies in order to increase both knowledge about youth activities and the likelihood that adolescents will abstain from problem behavior. Key monitoring literature suggests that some of these active monitoring strategies predict increases in adolescent problem behavior rather than protect against it. However, this literature has studied racially homogenous, low-risk samples, raising questions about generalizability. With a diverse sample of youth (N = 753; 58% male; 46% Black) and families living in high-risk neighborhoods, bidirectional longitudinal relations were examined among three aspects of monitoring (parental discussions of daily activities, parental curfew rules, and adolescent communication with parents), parental knowledge, and youth delinquency. Parental discussion of daily activities was the strongest predictor of parental knowledge, which negatively predicted delinquency. However, these aspects of monitoring did not predict later delinquency. Findings were consistent across gender and race/urbanicity. Results highlight the importance of active and involved parental monitoring strategies in contexts where they are most needed.