Research has shown social class differences in undergraduate engagement, yet we know little about the reasons for these differences. Drawing on interviews and participant observation with undergraduates at an urban, public comprehensive university, this ethnographic study investigates the academic engagement strategies of students from different social class backgrounds during their first two years of college. I find that first-generation and middle class students expend strenuous efforts to succeed, with first-generation students employing independent strategies and middle class students employing interactive, as well as independent, strategies. But because middle class students have a broader repertoire of strategies, which include those that are visible and valued by university faculty and staff, they are advantaged in the college context, or field, relative to their first-generation peers. This research shows how culture in the form of social class shapes undergraduates’ academic strategies and contributes to their unequal outcomes. It also points to the role of institutions in defining the implicit rules of engagement, such that middle class strategies of interaction are recognized and rewarded while first-generation strategies of independence are largely ignored.