This prospective, longitudinal investigation examined mechanisms proposed to explain continuities in parenting behavior across 2 generations (G1, G2). Data came from 187 G2 adults, their mothers (G1), and their children (G3). Prospective information regarding G2 was collected both during adolescence and early adulthood. G1 data were collected during G2's adolescence, and G3 data were generated during the preschool years. Assessments included both observational and self-report measures. The results indicated a direct relationship between G1 and G2 harsh parenting, and between G1 and G2 positive parenting. As predicted, specific mediators accounted for intergenerational continuity in particular types of parenting behavior. G2 externalizing behavior mediated the relationship between G1 and G2 harsh parenting, whereas G2 academic attainment mediated the relationship between G1 and G2 positive parenting. In addition, the hypothesized mediating pathways remained statistically significant after taking into account possible G2 effects on G1 parenting and G3 effects on G2 parenting.