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At a time when educational attainment in young adulthood forecasts long-term trajectories of economic mobility, better health, and stable partnership, there is more pressure on mothers to provide labor and support to advance their children’s interests in the K–12 system. As a result, poor health among mothers when children are growing up may interfere with how far they progress educationally. Applying life course theory to the National Longitudinal Study of Adolescent to Adult Health to investigate this possibility, we found that young adults were less likely to graduate from college when raised by mothers in poor health, especially when those mothers had a college degree themselves. Young people’s school-related behaviors mediated this longitudinal association. These findings extend the literature on the connection between education and health into an intergenerational process, speaking to a pressing public health issue—rising morbidity among adults in midlife—and the reproduction of inequality within families.