Twenty years on Myanmar has come full circle, repeating the events of 1988. Myanmar's Saffron Revolution has come to a brutal halt amidst public outrage worldwide. Violent repression, where the State turns its guns on its own citizens, has come into twenty-first century news screens, uniting those university students in the final years of the Cold War with their contemporary successors. ASEAN has issued its most strongly worded statement thus far on the situation in Myanmar in reaction to recent events. What does this recent practice, viewed against ASEAN's previous modus operandi, signify for those who are trying to understand ASEAN today? What are the true causes for ASEAN's latest policy shift? Is it truly a shift? What does constructive engagement cost ASEAN today? Is constructive engagement obsolete? What sorts of assumptions underpinned the policy of constructive engagement in the past and have those assumptions, and the world around ASEAN, changed? What does it mean to call for clearer action? Should ASEAN suddenly adopt a coercive or sanctions model of international law and expel Myanmar, or has it been on the right path all along by taking the view that membership of ASEAN would eventually alter Myanmar's behaviour? Does our experience of the effect, if any, of international legality on how countries behave tell us anything useful? In the face of calls for Singapore to cut ties with Myanmar, what does that mean and is it possible for Singapore to do so as an ASEAN member? In light of two decades of putting the spotlight on Myanmar, debate over sanctions and human rights in Asia, and geopolitical change, what would be the best way forward for ASEAN? Do techniques of legality provide ASEAN members some of the practical tools with which to understand and do the job of responding to today's issues? Against popular public opinion, the 21st Singapore Law Review Lecture will argue that there is both the means and opportunity today for a coherent, cautiously optimistic, regional response to the Myanmar crisis.