With varying levels of intensity, Southeast Asian countries have been experimenting with different modes of decentralization for over two decades. Significant debate exists about the success of these efforts, and some countries have recently attempted to reverse these measures by recentralizing political, fiscal, or administrative authority. To better understand the arguments over these institutional changes, we commissioned a set of articles from world-class scholars on the region, asking them to reflect on decentralization/recentralization debates within their countries of study. In this introductory article, we explore some of the key themes and findings from these contributions. An unmistakable tone of negativity pervades the pieces. Authors express either disappointment that decentralization did not achieve its lofty goals or was never given a chance to succeed by central leaders who: were reluctant to fully devolve power; issued contradictory legislation that undermined decentralization’s effectiveness; or used alternative levers to recentralize authority to negate the incipient decentralization measures. We probe some of the main drivers of the disappointment and offer some conjectures about the future of decentralization in the region.