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Few studies have explored the factors associated with the preference of medical students to pursue a specific specialty, and even fewer have observed how these preferences and factors change over time.A longitudinal survey of medical students was administered at the beginning of first year, second year, and clerkships from 2013–2016. Surveys included demographics and factors associated with their choice of specialty.Response rates were 78–94%. Students with mentors and research experience in any specialty were 3.4 times (P < .001) more likely to choose surgery by their third year of medical school. Surgical research experience on the first- and second-year surveys was associated with 39 (P < .001) and 10 times (P < .001) greater odds of preferring surgical specialties on their third-year survey. Medical students who had a surgery mentor during the first and second years were associated with 4 (P = .024) and 13 times (P < .001) greater odds of preferring surgical specialties on their third-year survey.Students who begin surgical research during their first year and develop relationships with surgeon mentors during their second year are significantly more likely to maintain an interest in surgical specialties.