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Sociological research has clearly demonstrated the important role that high parental expectations play in launching children on a successful life course trajectory. Parents with high levels of education tend to hold high educational expectations for their children, which influence children’s own motivation and achievement in school. However, it is unclear whether grandparents’ (G1) status, particularly their education, might influence parents’ (G2) expectations for their children (G3) independently of or in interaction with parents’ education. We begin to answer this three-generation question using prospective longitudinal data from 477 families in the Youth Development Study. Our results indicate that grandparents influence parents’ expectations for their children directly through income and educational expectations they held for the G2 parents when G2 were in high school, even after controlling G2 college attendance and income. G1 college attendance does not directly affect G2 expectations for G3 after accounting for other relevant family characteristics. However, G1 college attendance moderates the effect of G2 college attendance on their expectations for G3. If G1 did not attend college, then G2 college attendance does not significantly improve their expectations for G3. However, G2 college attendance does significantly boost their expectations for G3 if G1 also attended college. This is a clear example of resource multiplication, in which the largest “return on investment” for higher education accrues to families with intergenerational patterns of college attendance. This study highlights the need to expand the scope of status attainment research beyond the parent-child dyad to examine the influence of three or more generations.