Despite the need for a robust primary care workforce, the number of students and residents choosing general internal medicine careers continues to decline. In this article, the authors describe their efforts at the University of California, Davis School of Medicine to bolster interest in internal medicine careers and improve the quality of care for medically underserved populations through a tailored third-year residency track developed in partnership with the Sacramento County Department of Health and Human Services. The Transforming Education and Community Health (TEACH) Program improves continuity of care between inpatient and outpatient settings, creates a new multidisciplinary teaching clinic in the Sacramento County health system, and prepares residents to provide coordinated care for vulnerable populations. Since its inception in 2005, 25 residents have graduated from the TEACH Program. Compared with national rates, TEACH graduates are more likely to practice general internal medicine and to practice in medically underserved settings. TEACH residents report high job satisfaction and provide equal or higher-quality diabetes care than that indicated by national benchmarks. The authors provide an overview of the TEACH Program, including curriculum details, preliminary outcomes, barriers to continued and expanded implementation, and thoughts about the future of the program.