The purpose of this study was to investigate the mediation effects of children’s cognitive and noncognitive traits on the relationship between dropout mothers’ traits and their children’s educational expectations and to examine the interaction effects of dropout mothers’ General Education Development (GED) on children’s traits and educational expectations. The data were drawn from a series of National Longitudinal Survey Data. This study demonstrated the effect of mothers’ self-esteem on children’s educational expectations, which were mediated through children’s cognitive ability and self-esteem after controlling for the mothers’ cognitive ability, self-esteem, and socioeconomic status. Furthermore, mothers’ GED attainment moderated the relationship between children’s self-esteem and educational expectations. These findings provide better understanding of the intergenerational connections between cognitive and noncognitive traits and educational expectations.