Identifying the conditions, contexts, and processes through which children, adolescents, and adults acquire academic skills and subsequent educational attainments is of critical importance for developmental science and for policy and practice. This special issue of the Merrill-Palmer Quarterly was assembled with the aim of advancing understanding of the pathways through which educational attainments, broadly construed, develop across childhood and adolescence and the ways in which educational attainments are transmitted across generations. Four prospective longitudinal data sets were employed to address these aims. Two interrelated questions were addressed in each study: (1) Whether, and to what extent, do parents' educational attainments predict their offspring's academic skills, achievement orientations, and educational attainment? (2) What role do socialization experiences with parents and peers play in these predictive relations? The four empirical articles provide a coherent set of answers to these questions and in so doing shed important new light on the developmental processes through which academic skills and educational outcomes accrue.