Timor-Leste is in the process of addressing a key issue for the country’s health sector: a medical workforce that is too small to provide adequate care. In theory, a bilateral programme of medical cooperation with Cuba created in 2003 could solve this problem. By the end of 2013, nearly 700 new doctors trained in Cuba had been added to Timor-Leste’s medical workforce and by 2017 a further 328 doctors should have been trained in the country by Cuban and local health professionals. A few more doctors who have been trained in Indonesia and elsewhere will also soon enter the workforce. It is expected that the number of physicians in Timor-Leste in 2017 will be more than three times the number present in the country in 2003. Most of the new physicians are expected to work in rural communities and support the national government’s goal of improving health outcomes for the rural majority. Although the massive growth in the medical workforce could change the way health care is delivered and substantially improve health outcomes throughout the country, there are challenges that must be overcome if Timor-Leste is to derive the maximum benefit from such growth. It appears crucial that most of the new doctors be deployed in rural communities and managed carefully to optimize their rural retention.