This paper evaluates rural work location outcomes of an Extended Rural Cohort (ERC) program in medical school. Students nominate a preference and are contracted to the program at entry to the medical course, involving 2–3 years continuous rural training. Data included 2412 graduates from a large university medical school cohort study. Regression modeling compared 2017 work location of ERC participants, by their level of preference for the ERC and students who had other (similar or shorter duration) rural training with a metropolitan-only trained group. Students who entered medicine with ERC as their first preference commonly had rural background (95.5%) compared with second or lower preferences (61.5% and 40.4%, respectively). Multivariate regression modeling identified ERC participants were more likely to work rurally (OR: 2.69–3.27, compared with metropolitan-trained), though higher odds were associated with lower preference for ERC. However, non-ERC students undertaking a similar duration rural training by opting for this “year by year” after course entry, had the strongest odds of rural work (OR: 4.62, 95%CI: 3.00–7.13) and work in smaller rural towns (RRR: 4.08, 95%CI: 2.36–7.06). The ERC attracts rural background students and increases rural work outcomes. However, students choosing a rural training path of equivalent duration after course entry may be more effective and improve rural workforce distribution.