The authors examined the joint (interactive) roles of the Second Step curriculum (a validated social-emotional learning and bullying prevention program; Committee for Children, Seattle, WA) and parenting practices on students' behavioral and academic outcomes in Grades 5-8. Participants were 763 parents and their children from 22 schools (8 control and 14 treatment). A 2-level random coefficient model was conducted to assess the effect of parental monitoring on school outcomes, as well as the interaction between character development curriculum and parental monitoring. Results indicated that parental monitoring was a significant predictor of school behaviors and school grades. Furthermore, the Second Step curriculum moderated the relationship between parental monitoring and problem behaviors, prosocial behaviors, and grades at school. Specifically, in schools without the Second Step curriculum parental monitoring predicted higher school grades but had no impact on students' school behaviors. By contrast, in schools with the Second Step curriculum, parental monitoring predicted fewer problem behaviors as well as more prosocial behaviors. The study results highlight the joint influences of the family and the school in children's behavioral and academic trajectories. Results have implications for education and intervention, including improving the school climate, student behaviors, and learning or achievement.