This chapter offers an in-depth look at health politics and the compulsory health insurance system in North Macedonia. It traces the development of the North Macedonian healthcare system, characterized by the establishment of decentralized free-for-all-at-point-of-delivery health system during communism, which served as a basis for the current system. Since the early 1990s, when North Macedonia declared independence and started a transition towards democracy and a free market economy, North Macedonian health politics focused on permitting private provision, establishing a compulsory health insurance system, and integrating private services in the public insurance. Despite support from international organizations, the reform process was hampered by economic difficulties, inter-ethnic conflict, and the conflict with Greece regarding North Macedonia. As highlighted in the chapter, the main healthcare challenges have been to ensure the insurance system’s fiscal solvency, the conversion of primary care provision from local public health centers into private practices, and, since 2012, the integration of higher level private hospital services into the public system in order to reduce out-of-pocket payments and ensure equal geographical access.