This research studied the effectiveness of the Association of Southeast Asian Nations' (ASEAN) policy of constructive engagement toward Myanmar (Burma), with the aim of recommending appropriate improvements to this policy. Myanmar is one of the world's longest military-ruled dictatorships and is beset with many internal problems. Its government has been criticized by some countries and n-governmental organizations for human rights abuses and political suppression. There are also allegations of cross border criminal activities, such as human and drug trafficking, coordinated by criminal gangs in that country. Despite its reputation, Myanmar was accepted as an ASEAN member in 1997. Since then, the association is one of the few organizations in the world with diplomatic links to that country. ASEAN's approach of diplomatic engagement, commonly referred to as constructive engagement is geopolitically advantageous to ASEAN in many aspects. However, it runs contrary to the current policies of diplomatic isolation and ecomic sanctions imposed by some Western powers such as the US and the EU. This research has studied the effectiveness of constructive engagement from three angles -- an International perspective, a Regional perspective, and a Grassroots perspective. It has found that ASEAN should t only continue constructive engagement but that the association should offer even greater assistance to Myanmar. These actions will help improve the quality of life of Myanmar's citizens and strengthen the country, as well as generating regional benefits.