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Drawing on interviews with fifty first generation college students attending predominantly White, private residential colleges in the northeast, this paper explores the factors that shape students’ sense of belonging in these college settings. Student responses mirror what Nunez’s (2009) quantitative work describes as a “critical paradox”, wherein highly involved students are more likely to have a greater sense of belonging but also to articulate a more significant critique of the campus climate. However, our findings indicate that students may struggle to cultivate that tenuous sense of belonging and others may only feel a sense of belonging to particular niches within the campus community.