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How do undergraduates engage college officials? Existing explanations of help-seeking and engagement predict class-based engagement strategies. Employing 137 interviews with undergraduates and two years of ethnographic observation at an elite university, this article shows how undergraduates with disparate precollege experiences differ in their orientations and strategies toward help-seeking and engaging college officials, and considers the payoffs. Middle-class undegraduates report being at ease when engaging college officials. Undergraduates from working-class backgrounds, however, are split. The Privileged Poor—lower-income undergraduates who attend boarding, day, and preparatory high schools—enter college with cultural repertoires akin to those of their middle-class peers, are primed to engage college officials, and are proactive in doing so. By contrast, the Doubly Disadvantaged—lower-income undergraduates who remain tied to their home communities and schools before college—are more defensive when engaging college officials and withdraw from them. Through documenting the overlooked heterogeneity between lower-income undergraduates, this study outlines how precollege experiences have lasting influence on undergraduates’ cultural repertoires that is independent of family background. In all, this study sheds new light on the cultural underpinnings of education processes, mobility, and the reproduction of inequality in college that results from uneven access to institutional resources via college officials.