With the geopolitics of Southeast Asia and changing rapidly and substantially, an opportunity presents for a timely and thoughtful deliberation on the role ASEAN can play in the region. This enduring union of 10 member states has made great strides in becoming a formidable regional body. At the same time, the region is facing radically new and complex security and economic challenges. ASEAN is in a distinct and timely position to ably guide its members toward more sustainable security and prosperity in the years ahead, and to lead member states in the development of a uniquely ASEAN jurisprudence. In order to effectively grapple with those daunting challenges, ASEAN must consider new and innovative transboundary solutions, and work more deliberately across borders to enhance regional collaboration and implement existing agreements. The need to sustain a common regional identity and organizational coherence requires a fundamental rethinking of ASEAN’s institutional capacity and the reach of the ASEAN Secretariat. It is now imperative for ASEAN to help strengthen legal norms and establish effective rule-making systems in ASEAN member states so that the region can cope with the security and economic challenges it is facing.