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This study examines the role of cultural congruence—a fit between students and institutions in terms of expectations, habits, and behaviors, etc.—in the college transitions of a sample of low-income freshman at four-year, public institutions. Drawing on survey and interview data, the study finds that the process through which students initially “learn college” appears essential to understanding their later outcomes. In particular, moments of congruence are correlated with a typology of transition experiences as well as several academic outcomes, including persistence into the sophomore year. These findings suggest the need for greater institutional attention to how students manage and are supported during the transition to college, particularly by faculty members.