The focus of this article is Myanmar’s transition to democracy, which is taking place after almost half a century of military rule. The former military rulers are themselves the architects of transition. This article notes that one of the key challenges faced by military regimes during this kind of transition is the problem of “credible commitments”. In short, the issue is this: a transition will only be successful if it has the support of the political opposition and the public at large. But why should these groups believe in the promises of former tyrants? Problems of credibility and low expectations about the intention and capacity of the military to effect reform can cause destabilisation and undermine prospects for a successful transition. In worst case scenarios, instability leads to a resurgence of authoritarianism, or to a(nother) military coup. This article highlights the role of the Association of Southeast Asian Nations (ASEAN) in assisting the transition and stabilisation of Myanmar’s fledgling democracy. The argument is that ASEAN provides a means whereby Myanmar’s leaders can make credible commitments about their intentions in relation to liberalisation and democratisation, lending support to Myanmar’s reformist government at a crucial time in the transition to democracy. The article concludes that under certain circumstances, even regional organisations such as ASEAN, which are not comprised of a majority of democratic states, can (to a degree) influence perceptions about a democratising regime’s commitment to reform.