A theoretically informed model was estimated with the LISREL-VIII program using panel data from 1,384 mother-adolescent child pairs to examine processes by which mothers' adolescent school experiences measured in 1971 (Time 1) affected the adolescent school experiences of their children measured in the 1990s (Time 3) through mediating variables examined when the mothers were young adults in the 1980s (Time 2) and when they were parents of adolescents in the 1990s (Time 3). Results revealed two statistically significant paths from mothers' adolescent school experiences and psychological distress to their children's adolescent school experiences. This Intergenerational effect was mediated by mothers' early adoption of adult roles, psychological vulnerability, and low self-expectations, measured at Time 2, and by mothers' educational involvement, educational expectations, and family socioeconomic level, measured at Time 3.