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Montenegro, a small Balkan state, has to grapple with many economic issues. The labor market situation has not improved in recent years. The unemployment rate has remained stubbornly high, especially among young people. What is more, around 20% of the employed in fact work in the informal economy. Large numbers of the unemployed pose a serious challenge not only to the Montenegrin economy, but also to the capacities of social security system. The economic situation and the level of unemployment also have an impact on the scale of emigration. The aim of this chapter is to present two key challenges to the social security of Montenegro – unemployment and emigration. The analytical basis of this research is a review of economic, sociological and security-related literature, including a secondary data analysis of public policy documents, statistics and media reports. Considering the subject of this study, qualitative research seemed necessary while the research topic justifies the application of content analysis and desk research in order to analyze secondary data sources. The chapter begins by presenting briefly the economic situation in Montenegro – what changes have taken place in the economy over the last 30 years. Next, the unemployment level in Montenegro is described. The last part of the analysis presents the problem of emigration resulting from the economic situation in Montenegro and the level of unemployment. Despite efforts to accelerate economic growth and reduce the level of unemployment, economic slowdown is expected, which will in turn further increase migration flows.