Macedonia has reached its long desired strategic goal to become a full NATO member state in March 2020. This article sheds light on the peculiarities associated with the accession process of this small and impoverished country, and the unique criteria it had to fulfill in order to finally achieve its desire to join NATO. The key questions that are addressed include the following: Does Macedonia’s membership bring peace and progress to the troublesome region? What does membership mean in terms of internal cleaveages, especially concerning socio-economic and inter-ethnic difficulties? The key premise is that NATO membership would not enhance the country’s transformation to the better; membership came at too high a cost, which may instigate an even greater instability.