Includes supplementary materialThis thesis examines retention in the Navy Medicine and Surface Warfare communities using an administrative dataset from Defense Manpower Data Center and the Milestone Survey from the Office of the Deputy Chief of Naval Operations (Manpower, Personnel, Training, and Education) (OPNAV N1). Through a combination of descriptive and multivariate logistic models, we find that being a female, having dependents, and being Hispanic are most correlated with separation outcomes in the administrative data. Our survey results indicate that the top reasons for leaving are impact on family, civilian job opportunities, and work-life balance. The top reasons for staying are medical and dental benefits, monetary compensation a...