The Brussels-facilitated dialogue between Kosovo and Serbia has been marked by periodic breakthroughs, political fanfare, and declarations of historic progress. However, a closer inspection of its key milestones—the 2013 Brussels Agreement, the 2015 clarifications on the Association/Community of Serb-majority Municipalities (ASM), and the 2023 Agreement on the Path to Normalization (APN)—reveals a striking pattern: partial success, followed by prolonged stalemate. Rather than establishing a cumulative normalization process, these agreements have produced short-term gains that repeatedly stalled implementation. This chapter analyzes the structural reasons for the EU’s limits in producing a comprehensive normalization of relations with Kosovo. Suppose the Union cannot shepherd a comprehensive normalization process between two aspiring members on its doorstep. What message does that send to countries like Ukraine or Georgia, where the stakes are higher and the actors far more adversarial? The answer lies not only in institutions and approaches but also in personalities.