The purpose of the current investigation was to explore whether monitoring behavior (i.e., parental solicitation, child disclosure, and parental involvement) was directly and indirectly (via parental knowledge and parent–youth openness) related to adolescent adjustment (i.e., antisocial behavior, substance use, and school grades). The sample consisted of 206 families with adolescents (ages 10–18 years) from predominantly low-income, high-risk neighborhoods. Monitoring behavior (parent reports), parental knowledge and parent–youth openness (youth reports), and adolescent adjustment (parent and youth reports) were all based on questionnaire data collected during a laboratory assessment. Results showed that when the monitoring behavior factors were examined simultaneously, only child disclosure was significantly and inversely related to youth antisocial behavior. In contrast, only parental involvement was significantly associated with less substance use. Moreover, school grades were significantly and incrementally predicted by both child disclosure and parental involvement. Parental solicitation was not significantly related to any of the adolescent outcomes. The findings also demonstrated evidence of indirect effects (via parental knowledge) in the link between monitoring behavior and adolescent adjustment. Implications regarding the socialization process during adolescence are discussed.