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This study uses an ecological framework to examine the associations between parental monitoring and a variety of indicators of adolescent adjustment. Specifically, investigators examined whether higher levels of parental monitoring were associated with higher adolescent grade point average, lower levels of adolescent depression, and lower levels of adolescent sexual activity and minor delinquency, and whether these relations were moderated by gender, grade level, or mothers’ work status. Participants were 424 7th to 12th graders from a single rural school district in central Pennsylvania. Bivariate correlations indicated that parental monitoring had strong associations with all indicators of adjustment for both boys and girls, with the exception of boys’ depression. Gender and grade level simultaneously moderated the relation between parental monitoring and adolescent delinquency, with the effect of parental monitoring increasing across grade level for boys, and decreasing with grade level for girls. Furthermore, maternal employment moderated the relation between monitoring and adolescent delinquency and sexual behavior. For both boys and girls, monitoring was a significant predictor of problem behaviors among adolescents whose mothers worked full time. Thus, effective monitoring may compensate for a lack of direct supervision. However, gender further moderated these associations. Specifically, the relation between monitoring and adjustment was also significant among girls when their mothers were not working and among boys when mothers worked at least part time.