The children of teen mothers are at elevated risk for becoming teen parents themselves. The current study aimed to identify how levels of mothers' education were associated with risk of teenage childbearing for children of teen versus nonteen mothers. Through structural equation modeling, we tested whether children's environmental and personal characteristics in adolescence and subsequent sexual risk behaviors mediated the relationship between their mothers' educational attainment and their risk for teenage childbearing. With multiple-group models, we assessed whether the associations of maternal educational attainment with children's outcomes were similar for the children of teen and nonteen mothers. The sample (N = 1,817) contained linked data from female National Longitudinal Survey of Youth, 1979 (NLSY79) participants and their first-born child (son or daughter) from the NLSY79 Children and Young Adults. The mediating pathways linking higher levels of maternal education to lower risk for teenage childbearing, and magnitudes of the associations, were mostly similar for children of teen and nonteen mothers. However, nonteen mothers experienced greater associations of their high school diploma attainment (vs. no degree) with some of their children's outcomes. Also, the association of earning a high school diploma (vs. a GED) with household incomes was greater for nonteen mothers; there was no significant difference between degree types for teen mothers. Findings provide support for teen mother secondary school support programming, but point to a need for further research regarding the long-term behavioral and social outcomes associated with the high school equivalency certificate for teen mothers and their children.