When ASEAN celebrated its fiftieth anniversary, it was asked if an organization founded on principles appropriate for the 1960s remains relevant today. Its critics point to the organization’s recent failures to indicate that continued reliance on the “ASEAN Way” puts it on the road to irrelevance. Its defenders argue that the peace and stability that ensued since the Association’s formation are testimony that the ASEAN formula works. Both conclusions are based on what commentators on either side of the debate believe ASEAN’s role should be. This paper argues that an assessment should, instead, be based on what its members want it to do, expressed through policy announcements and documents like the ASEAN Charter. It should also consider the totality of its mandate from diplomacy to economics. Viewed in this way, the grouping has accomplishments to be proud of, but also some failures to regret. The “ASEAN Way”, upheld steadfastly by its member countries’ leadership, has been instrumental to both its successes and failures. Overall, while ASEAN may not live up to the expectations of its critics, its achievements in some areas do suggest its continued relevance even under vastly changed circumstances, both domestic and external.