Developments at the international arena in the last decade were not favorable for the strengthening of Kosovo’s statehood. Serbia’s hostile policies towards Kosovo, the increase of malign Russian and Turkish influences in the Balkans, the EU’s enlargement fatigue and the lack of unity of its members towards Kosovo’s independence, have become major and long-term challenges and threats to Kosovo’s sovereignty. With the aim of analyzing these external threats and challenges in a comprehensive framework, Columbia University and the Kosovar Institute for Policy Research and Development (KIPRED) have joined their efforts in bringing together a group of prominent scholars and opinion-makers from Kosovo, Greece, Macedonia, Serbia, the United States of America and Turkey. This aim of this publication is not to offer any specific policy recommendations to national and international stakeholders. Instead, it provides ideas for Kosovar and Western decision and policy makers through a comprehensive analysis of the context related to challenges and threats to Kosovo’s statehood and sovereignty, and to the overall stability and security of the region.