In 2007, the Association of Southeast Asian Nations attempted to celebrate its 40th founding anniversary with a bang as it was about to set another milestone, which is the signing of the ASEAN Charter. However, the celebration was overshadowed by the political crisis in Myanmar following the military's crackdown on protesting monks and their democratic supporters. The inability of ASEAN to influence events in that country became the focus of public attention in the region and the international community. Even the much-vaunted milestone of finally having an ASEAN Charter was a major disappointment for many in Southeast Asia as the final document signed by ASEAN leaders was everything but bold, forward-looking, and transformative. It became an object of criticism mainly by some think tanks and civil society groups in the region because it paled in comparison to the recommendations of the Eminent Persons Group that drafted the blueprint of what the ASEAN Charter should look like. This article describes the major milestones and turning points of ASEAN's regionalism project over the last forty years. It also attempts to identify the major issues and challenges to ASEAN's community building efforts in the future. The main argument of this article is that ASEAN's continuing relevance to the people of the region can be ensured only if it seriously opens up to greater participatory regionalism. Only then can ASEAN be transformed into a truly people-centered organization.