Serbia is negotiating European Union (EU) membership, a process that started in 2014 after the Brussels-mediated agreement between Kosovo and Serbia was signed in April 2013. Although the Federal Republic (FR) of Yugoslavia (Serbia and Montenegro) was officially included into the EU’s Stabilization and Association Process soon after the fall of the Milošević regime in October 2000, complex political issues have prevented its faster progress toward the EU. EU measures after 2001 in the areas of financial assistance, trade, and legal harmonization have sustained in a major way the country’s political and economic reforms, facilitating fast economic integration with the EU economy, financial and banking integration, the adoption of many laws in conformity with the acquis communuataire, new business opportunities, and increasing foreign direct investment. However, the Serbia–EU integration process has also been accompanied by strict political conditionality that has greatly delayed the establishment of contractual relations. Despite major efforts of various governments to comply with EU conditions, it was only in late April 2008 that Serbia concluded a Stabilization and Association Agreement with the EU, which has paved the way for obtaining candidate status in 2012 and the opening of EU accession negotiations in 2014. In the meantime, EU’s enlargement negotiations framework has been strengthened further, making the negotiation talks much more complex and demanding. In addition to Serbia’s insufficient compliance with accession criteria, particularly reforms of the judiciary and public administration, the contested issue of Kosovo’s independence continues to pose a major threat to Serbia’s entry into the EU. Despite the absence of a common position on the part of the EU, given that Kosovo has still not been recognized by five EU member states, the limited progress in the Belgrade–Priština EU-facilitated dialogue represents one of the major obstacles for Serbia’s EU membership. Serbia’s entry into the EU, which could possibly take place in 2025, is likely to bring many benefits to the country and its population, but also to the EU, as this is a region of not only risks but also opportunities.