Purpose: Workforce shortage is a contributing cause of health inequality in rural Australia. There is inconclusive evidence demonstrating which factors cause doctors to choose rural practice. This study’s objective is to determine predictive factors for medical students’ intent to work rurally and for graduates’ current rural employment location choice. Methods: This prospective cohort study, utilized data gathered from the University of New South Wales about students and graduates who had spent one or more years in a Rural Clinical School. Participants were final year students and graduates already working in Australia. Stepwise logistic regression was used to determine predictive factors for the two outcomes. Results: Predictors for student intent to work rurally are rural background (odds ratio [OR], 7.16; 95% confidence interval [CI], 2.59–19.53), choosing to study at the Rural Clinical School (OR, 8.72; 95% CI, 1.32–57.63), and perceiving rural areas as opportunistic for career advancement (OR, 1.69; 95% CI, 1.15–2.49). Predictors for graduates currently working in a rural location are Bonded Medical Program participation (OR, 6.40; 95% CI, 1.15–35.59) and personal altruism (OR, 1.91; 95% CI, 1.02–3.57). Conclusion While intent is predicted by having a rural background, choosing to study at the Rural Clinical School and perception of rural areas as having positive career opportunities, a current rural workplace location among graduates is predicted by holding a bonded medical position and a desire to serve an under-resourced population. Maintaining the Bonded Medical Program and clear communication regarding training pathways may increase numbers of rural doctors.