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Compared to continuing-generation students, first-generation students face additional structural barriers to their belonging in selective intuitions (e.g., research universities). We examined first-generation (N = 601) and continuing-generation (N = 832) students’ perceptions of belonging uncertainty, motivation, and achievement at three research universities. A multi-group path analysis suggested that belonging uncertainty was negatively related to success expectancies and positively related to costs (perceived drawbacks) in math for both first-generation and continuing-generation students. Importantly, expectancies and costs mediated the relations of belonging uncertainty with achievement for first-generation students but not for continuing-generation students. These findings shed light on the mechanisms through which belonging uncertainty impacts students’ achievement and has implications for narrowing equity gaps between first-generation and continuing-generation students in selective institutions.