The extent to which the family environment is characterized by stress may have a substantial impact on life-course trajectories of young people. Illicit drug use is a fairly common part of these trajectories. This paper estimates the direct impact of family stressors on the progression to problem cannabis use, as well as their indirect effects via the youth's school experience among adolescents in Ontario. The results suggest that family stressors have direct and indirect effects increasing the probability of cannabis use outcomes. The implications of these more complex associations between factors believed to influence adolescent drug use trajectories are discussed.