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Scholars have found first-generation college students (FGCS) encounter enormous challenges in college enrollment. Extant FGCS scholarship mostly adopts qualitative approaches based on regional investigations or employs quantitative methods with dated datasets. Using a more recent, nationally-representative dataset, the High School Longitudinal Survey of 2009 (HSLS:09) and multiple regression analysis, our research investigates how habitus (i.e., one’s dispositions) and school context can predict college enrollment among FGCS. We find evidence of the important role practitioners play, specifically counselors, in helping FGCS enroll in college through discussions regarding financial aid. This study discusses the types of targeted interactions that educational stakeholders (e.g., counselors, teachers) can facilitate with their students to support FGCS access to higher education.