This chapter focuses on the EU’s future enlargement plans. In a time of war and instability, the enlargement plans have gained new momentum, and the chapter addresses the question of how the EU can (and should) manage the risks and opportunities associated with a new wave of enlargement. It first presents various incentives for an EU enlargement: economic, geopolitical, and normative. It then examines the formal and informal procedures of the enlargement process, which has become increasingly lengthy and evaluative. Against this background, it provides an overview of the current enlargement processes in two distinct regions: the Western Balkans and the Eastern Partnership, followed by a discussion of the EU’s capacity to enlarge and various proposals for institutional reforms to manage a new enlargement. The chapter concludes with a comparison of the Western Balkans and the Eastern Partnership in terms of the challenges and opportunities of enlargement. It also examines the broader dilemmas that the EU is facing in this process. It concludes that the EU should first prioritise internal unity on the core issue of whether it wants to enlarge, and then show endurance and patience throughout the process.