Expectations about the future direct effort in goal-oriented action and may influence a range of life course outcomes, including educational attainment. Here we investigate whether such expectations are implicated in the dynamics underlying the persistence of educational advantage across family generations, and whether such dynamics have changed in recent decades in view of historical change. Focusing on the role of domain-specific (educational) and general (optimism and control) expectations, we examine parallels across parent-child cohorts in (a) the relationships between parental socioeconomic status (SES) and children's future expectations and (b) the associations between children's future expectations and their academic achievement. We estimate structural equation models using data from the prospective multigenerational Youth Development Study (N = 422 three-generation triads [G1-G2-G3]; G1 M[subscript age] in 1988 = 41.0 years, G2 M[subscript age] in 1989 = 14.7 years, G3 M[subscript age] in 2011 = 15.8 years; G2 White in 1989 = 66.4%, G3 White in 2011 = 64.4%; G1 mean annual household income, converted to 2008 equivalents = $41,687, G2 mean annual household income in 2008 dollars = $42,962; G1 mode of educational attainment = high school, G2 mode of educational attainment = some college). We find intergenerational similarity in the relationships between parental educational attainment and children's future expectations. Children's educational expectations strongly predicted their academic achievement in the second generation, but not in the third generation. With educational expansion, the more recent cohort had higher educational expectations that were less strongly related to achievement. Overall, the findings reveal dynamics underlying the persistence of educational success across generations. The role of future expectations in this intergenerational process varies across historical time, confirming a central conclusion of life span developmental psychology and life course sociological research that individual functioning is influenced by sociocultural contexts.