Military Service Academy graduates have a unique pathway to surgical careers and unique insights into military life from their time as cadets. Whether going directly to medical school or entering after a period of service, cadets often have very successful and long careers as military surgeons. The qualities that contribute to success as cadets closely align with the core competencies required for success in medical school and residency. There are many options for civilian and military general surgery residency and subspecialty fellowship training, as well as career advancement as a military surgeon. Service academy graduates must carefully consider the service obligations and career implications of their residency and fellowship choices.