Admirers of the Association of Southeast Asian Nations (ASEAN) are impressed with the fact that it continues to exist and that an outright war has never broken out between its members. Also often praised is the value to the region of promoting cooperation through the consensual process known as the ‘ASEAN Way’. If ASEAN is a talk shop, these observers say, talking is at least better than fighting. ASEAN's increasingly numerous and vocal critics reply that by valuing process more than product, consensus over accomplishment, the organization is failing to respond to urgent real-world challenges in Asia. Not least among such challenges is Chinese expansion in the South China Sea (SCS) and the stated intention of incoming US president Donald Trump to pull his country out of the Trans-Pacific Partnership (TPP). Only four ASEAN members have claims in the SCS and only four are in the TPP, but the sea's and the treaty's futures matter for the rest of the region as well. The fact of Chinese advancement and the risk of American disengagement are endangering the autonomy and relevance of ASEAN, not to mention the repercussions of Sino-American escalation. Already weakened by internal dissensus, the group's ability to negotiate as a group with China on maritime security has been blocked by Beijing's insistence on bilateral talks. Chinese material largesse has coopted Cambodia into vetoing any ASEAN agreement to restrain, moderate, or even question China's designs on the heartwater of Southeast Asia. The ASEAN Way is being used against ASEAN itself. Heightened uncertainty as to America's future role in and commitment to the region further heightens security concern. In its 50th anniversary year, Southeast Asians would do well to think outside the increasingly marginalised, internally divided, and procedurally restricted box that ASEAN has become. Three ideas already in circulation illustrate the kind of creativity that ASEAN will need if it is to sustain its acknowledged historical success in fashioning an independent political and economic identity for Southeast Asia.