The transition from active duty military service to civilian surgical practice involves careful planning and understanding of available benefits and career pathways. This chapter outlines key considerations for military surgeons, including retirement, separation, and Reserve service options. It emphasizes early preparation, ideally 1–2 years before transition, to ensure a smooth process. The chapter explores different employment models like private practice, hospital employment, and locum tenens, discussing compensation, work-life balance, and contract negotiations. It also highlights the importance of gathering accurate documentation, such as medical records and DD214 forms, for future credentialing and accessing VA benefits. Overall, this guide provides essential insights to help military surgeons make informed decisions and transition successfully to civilian careers.