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.