The historic Prespa Agreement about the name issues between (now) North Macedonia and Greece marked an important turning point for North Macedonian aspirations for NATO membership and the European Union. It also showed that progress in the region is possible with committed and responsible leadership. Other key issues with both country-level and regional consequences, though, remain unresolved: functionality of Bosnia and Herzegovina as a state and the dispute between Kosovo and Serbia over Kosovo’s status stand out. Other issues, though, that range from weak rule of law, massive immigration of the younger population and criminal networks that reach highest echelons of the political establishment pose equal challenges with long-term consequences. This seminar will outline some of the key issues that the region (and individual states) has been grappling with as it enters into its fourth post-socialist and post-war decade. It will also provide a discussion about whether we have seen a progress or deterioration in democratisation and peaceful relations in the region and why that might be the case.