The case for a more diverse health-care workforce has never been stronger given the rapidly changing demographics of the United States and the continued underrepresentation of certain racial and ethnic groups across the health professions. To date, progress toward diversifying the health-care workforce has been and continues to be deterred by a mix of factors at the societal, institutional, and individual levels. Since the 1970s, the Federal government has invested resources in initiatives that support the training and development of the existing workforce as well increase the supply of new health professionals—particularly those from underrepresented minority groups and/or from disadvantaged backgrounds. However, limited studies have been published detailing the processes, outputs and, where available, outcomes of such investments across multiple years. This article describes how the Health Resources and Services Administration’s Bureau of Health Workforce used retrospective case study methodology to evaluate processes and outputs associated with the Scholarships for Disadvantaged Students program—an over US$40 million annual Federal investment aimed at offsetting tuition costs for health professions students from disadvantaged backgrounds—over a 5-year period. Lessons learned and recommendations for strengthening the program’s design and requirements are provided.