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.