Intergenerational transfer of risk between mothers and children, based on mothers' childhood aggression and social withdrawal, was examined in an inner-city sample. Each of the 3 studies reported involved a subset of the 909 female participants in the Concordia Longitudinal Risk Project, initiated when the participants were of school age. Using medical records, Study 1 (n = 853) focused on prediction of teen motherhood, delivery complications during childbirth, multiparity, and close spacing of births. Study 2 (n = 428) examined pathways to school dropout and teen parenthood. Study 3 (n = 89) involved prediction of observed parent and child behavior from mothers' childhood characteristics. Mothers' childhood aggression was consistently predictive of negative outcomes in each area of intergenerational risk, especially when combined with social withdrawal and low levels of academic achievement. Education was protective: Mothers' years of schooling predicted positive outcomes.