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This study examines the relationship between parental monitoring and youth violent delinquency, as well as the extent to which this relationship may be influenced by the school context. The study is based on data from the International Youth Survey (2006) which gathered information from a sample of students in grades 7, 8 and 9 attending Toronto schools. Findings indicate that a low level of parental monitoring is associated with a higher likelihood of youth violent delinquency, and this effect is stronger when youth attend schools where the prevalence of delinquency among the student population is high. This finding supports the hypothesis that the negative influence of low parental monitoring is magnified when youth are also exposed to a pool of delinquent peers, and further suggests that the effectiveness of particular parenting strategies may vary depending on the environments to which youth are exposed.