Scholars argue that lower-income undergraduates’ transition from segregated, distressed communities to college fosters heightened senses of difference and alienation in college. I call undergraduates socialized and educated in these contexts the Doubly Disadvantaged. Extant research, however, overlooks undergraduates who participate in pipeline initiatives that place lower-income students in elite boarding, day, and preparatory schools, permitting them greater exposure to wealth, whites, and privilege. I call undergraduates who travel this alternative route the Privileged Poor. This chapter investigates how differences in the Doubly Disadvantaged and Privileged Poor’s precollege experiences influence their experiences with class marginality and culture shock in college.