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Before gaining independence, the social security system of the Republic of North Macedonia was based on centralized Yugoslav Federation policies. Only after 1991 were concrete measures taken to establish a functional social security system in order to best meet the needs of its citizens. The Stabilization and Association Agreement between Macedonia and the EU requires that social security be adapted to the new social and economic requirements of society and the level of protection of the health and safety of workers be improved. The main rights of citizens regarding the social security system are ensured by the Constitution. The pension and disability system functions on the basis of the Principles of Solidarity (otherwise referred as the Pay-as-you-go (payg) principle) and the healthcare insurance system is based on compulsory and voluntary insurance. The aim of this chapter is to present theoretical and empirical views of the social security system of the Republic of North Macedonia through the doctrinal approach, with emphasis placed on health, pension and disability insurance, as well as the challenges present in this state. The development of the social security system will depend on demographic change and may only be achieved through reform and adapting to new social circumstances.