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How do undergraduates engage authority figures in college? Existing explanations predict class-based engagement strategies. Using in-depth interviews with 89 undergraduates at an elite university, I show how undergraduates with disparate precollege experiences differ in their orientations toward and strategies for engaging authority figures in college. Middle-class undergraduates report being at ease in interacting with authority figures and are proactive in doing so. Lower-income undergraduates, however, are split. The privileged poor—lower-income undergraduates who attended boarding, day, and preparatory high schools—enter college primed to engage professors and are proactive in doing so. By contrast, the doubly disadvantaged—lower-income undergraduates who remained tied to their home communities and attended local, typically distressed high schools—are more resistant to engaging authority figures in college and tend to withdraw from them. Through documenting the heterogeneity among lower-income undergraduates, I show how static understandings of individuals’ cultural endowments derived solely from family background homogenize the experiences of lower-income undergraduates. In so doing, I shed new light on the cultural underpinnings of education processes in higher education and extend previous analyses of how informal university practices exacerbate class differences among undergraduates.