Inherited privilege and status remain powerful factors in the distribution of opportunity in American life. These transfers of socioeconomic resources across generations are facilitated by the links between adult educational attainment and children's cognitive skills. Our current study expands the notion of social reproduction beyond this narrow two-generation approach to investigate the links between grandparents' educational attainment and their grandchildren's academic abilities. Using a nationally representative sample of over 13,000 children who participated in the Early Childhood Longitudinal Study-Kindergarten Cohort (ECLS-K), we find that familial advantages in human capital persist over time and that these advantages are associated with improved cognitive outcomes among later generations. Even after controlling for a wide array of socioeconomic and demographic characteristics, young children with college-educated grandparents possess stronger literacy and mathematics skills at the start of formal schooling. Propensity score approaches, which address concerns regarding the endogeneity inherent in the topic, yield similar results, suggesting the robustness of our findings.