BACKGROUND AND OBJECTIVES: While some family medicine residency programs are designed to train residents in community health centers (CHCs) for future careers serving underserved populations, there are few outcome studies on such programs. Our residency program provides three options for ambulatory health center training, but otherwise residents participate in the same curriculum. We analyzed relationships between ambulatory training site and likelihood of practice in health professions shortage areas (HPSAs). METHODS: We sent a mail survey to all graduates of one family medicine residency about practice locations, types, and populations; influences on practice choice; and sociodemographic characteristics. RESULTS: Training in a CHC had a statistically significant association with the likelihood of practice in an HPSA for both initial and current practice. Training in a rural residency site was associated with initial and current rural practice. Logistic regression analysis showed that physicians who completed ambulatory training in the CHC were nearly six times more likely to report having practiced initially and four times more likely to cite current practice in an HPSA. CONCLUSIONS: Outpatient CHC residency training increases the likelihood of practice in an underserved setting. This finding has policy implications for supporting workforce training in practice settings that care for underserved populations.