Persistent medical workforce shortages in rural Australia continue to undermine equitable access to healthcare. This commentary explores key barriers and enablers to rural medical graduate retention, focusing on the role of rural immersion programs, systemic training constraints, and evolving models of end-to-end rural medical education. While initiatives such as the Rural Clinical Schools, John Flynn Placement Program, and Murray–Darling Medical Schools Network have enhanced rural exposure, the lack of accessible specialty training pathways and professional support in rural areas continues to disrupt continuity. The mismatch between medical graduate output and vocational training availability compounds the issue. A coordinated effort involving universities, specialist colleges, government, and communities is essential to establish integrated training pipelines. End-to-end rural training, expanded regional training hubs, cultural competence, and community integration are critical components of a sustainable solution. Addressing these multifactorial challenges offers an opportunity to build a resilient and regionally distributed rural medical workforce.