The New South Wales Rural Resident Medical Officer Cadetship Program began in 1988 as a strategy to increase the numbers of junior doctors in rural hospitals. This article outlines the results of an evaluation undertaken in 2014. Specifically, it will look at where former cadets who entered the program between 1989 and 2010 were working in 2014, what training programs they chose and their attitudes toward the program. Data were collected using a semi-structured questionnaire sent to all the former cadets who entered the program from 1989 until 2010. This included self-administered questions relating to background (where the majority of the students' primary schooling was undertaken), vocational training, current role, current work location and attitudes towards the cadetship. Responses were received from 142 of the 211 cadets in the study (67%). Of the 142 former cadets who responded to the questionnaire, 90 had completed a vocational training program and were working as fully qualified medical practitioners. A further 44 were trainees, six were non-specialist hospital doctors and two were no longer practising. Overall, the most popular vocational training programs among fully qualified doctors and trainees combined were general practice, anaesthetics/intensive care and emergency medicine. Over half of the cadets included in the analysis (<i>n</i>=74, 53%) were working in rural areas (Australian Standard Geographical Classification Remoteness Areas 2-5) in 2014 and practice location was significantly (<i>p</i><0.001) influenced by career choice. Of the cadets working in rural locations, the majority (58%) were working as general practitioners while 38% had chosen other specialties and 4% were working as hospital non-specialists. An equal proportion of cadets came from urban and rural backgrounds while a small proportion grew up overseas. The cadets with rural backgrounds were more likely to choose general practice than those from urban backgrounds. A similar analysis of cadets comparing geographic background and practice location showed cadets of rural background were more likely to be working in a rural location than cadets of urban background. The cadetship is an effective link between medical school and rural practice. The success of the program relies in part on the mentoring, networking and other educational opportunities available to cadets, which serve to foster their interest and provide a structured pathway to long-term rural practice. It has been demonstrated that targeted incentive based scholarship schemes with a return-of-service component can be beneficial, particularly where they include ongoing support and reinforcement throughout the transition from undergraduate to postgraduate training.