The dialogue between Kosovo and Serbia facilitated and mediated by the EU and strong U.S. support is a critical part of sustainable peace, stability, and the road to the European integration of the Western Balkans. This article seeks to provide the mediators’ insights into the process of dialogue by outlining the factors and circumstances in which it is being developed, as well as analyzing strategies that lead toward desired success, peace, stability, and the EU integration of the Western Balkans. The article discusses the important issues linked with the dialogue that is being facilitated and negotiated by the EU, including essential activities, challenges, difficulties, obstacles, antagonism (inner and international), the approach the EU facilitators/mediators undertake as well as the reaction and the expected results that the parties involved in the process have regarding reaching a final solution to the dispute. The researchers of this paper used the methods of legal analysis, comparative analysis, and teleological analysis. The study is an update of the work done in the field by the authors and aims to contribute to further political, diplomatic, and academic debate developed in this field locally and internationally.