Researchers and policymakers argue that expanding college access is one way to increase opportunities for students who would become the first in their families to enroll in a postsecondary institution. This article uses measures of educational attainment in the previous two generations to consider whether parents' own histories of educational mobility and reproduction explain inequalities in how students prepare for college. Results suggest differences across generational categories in the types of colleges to which students apply and in the effects of parent-student discussions about topics related to college planning. These differences are explained by distinguishing the resources some families acquire through upward mobility from the resources that accumulate in families where educational privileges have been previously reproduced.KEYWORDS: college entry, educational mobility and reproduction, multigenerational inequalities, parents and families P arents' educational attainments are closely associated with the postsecondary opportunities students pursue. Students who have a parent who attended a four-year college have been shown to benefit from that parent's knowledge of how to ''continue [the] family tradition' ' (Terenzini et al., 1994, p. 63) of higher education. As a result, the pathways leading to college for these students have been called ''simple, linear, and predictable'' (Hossler, Schmit, & Vesper, 1999, p. 2). In contrast, ''first-generation students'' are less likely to complete the necessary steps to continue their educational careers after high school, in part because their parents cannot share personal experiences about applying or transitioning to college (Cabrera & La Nasa, 2001;Engle, 2007;Goldrick-Rab, 2007;Horn & MATTHEW LAWRENCE is visiting assistant professor of sociology at Reed College, 3203 SE Woodstock Blvd, Portland, OR 97202; e-mail: mjclawrence@aya.yale.edu. His research focuses on multigenerational approaches to educational inequality and prospective models of educational reproduction.