This study examined the relationship between the timing of maternal education and children’s educational attainment and the extent to which this relationship differs by gender. I used data from the National Longitudinal Survey of Youth 1979 and the Child and Youth Survey to determine the timing of mothers’ education relative to the birth of their children, with additional predictors associated with children’s educational attainment included in quantitative analyses. ANOVA analyses identified statistically significant differences in educational attainment among the children grouped by mother-category, based on the timing of their mothers’ education, and between genders. Regression analyses found no statistical difference between children whose mothers earned bachelor’s degrees before birth and those whose mothers were in college while mothering, but a large gap in attainment for children whose mothers did not attend college. Significant predictors, especially children’s grades, educational expectations, type of high school, and socioeconomic status, were found to predict children’s attainment. The findings inform a discussion about the extent to which a mother’s return to postsecondary education serves as a force for social mobility for her children and the extent to which the timing of maternal education facilitates social reproduction of education.