In this prospective longitudinal study (N = 585) we examined intergenerational links in level of educational attainment. Of particular interest was whether family background characteristics, parenting in early childhood and early adolescence, and school adjustment and performance in middle childhood accounted for (i.e., mediated) continuity and amplified or attenuated (i.e., moderated) continuity. Family background data, including mother education level, were collected when the children were age 5 years; parenting was assessed at ages 5 and 12; and school adjustment data (behavior problems, peer acceptance, academic performance) were collected in the first four years of elementary school. Cross-generational continuity in educational attainment was moderate (r = .38) and largely indirect via children's academic performance in elementary school and mothers' academic involvement in early adolescence. Moderator analyses indicated greater cross-generational continuity in single-parent families; in families low in proactive teaching, monitoring, and academic involvement; and in families with lower-IQ children who performed poorly in school and were disliked by peers. These findings suggest that distal and proximal family and child characteristics may serve as crucial processes in the intergenerational transmission of low educational attainment.