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This research investigates the social reproduction of inequality by drawing on prospective longitudinal data from three generations of Youth Development Study respondents. It examines intergenerational influence on adolescents’ educational plans, as well as a relatively under-studied dimension of the adolescent self-concept with potential relevance for educational attainment, academic self-esteem. A structural equation model, based on 422 triads, finds evidence that the sources giving rise to the development of G3 children’s achievement orientations are not only the result of G2 parental contemporaneous influence. They also extend back, in both direct and indirect ways, to the G2 parents’ own conceptions of their ability and their educational plans when they were adolescents during high school, and to the G2 parents’ educational attainments. G3 children’s achievement orientations are also found to be influenced indirectly by their grandparents’ socioeconomic accomplishments and by the expectations the G1 grandparents had more than 20 years earlier for the G2 adolescents.