The process of engaging the Democratic People’s Republic of Korea stands at a crossroads that presents challenges as well as opportunities. We believe that the Association of Southeast Asian Nations (ASEAN) can indirectly help to facilitate North Korean reforms in three ways: (i) Political: via ASEAN’s ability to function as a neutral facilitator of dialogue; (ii) Economic: as models of economic reform for North Korea (particularly based on the experiences of Singapore and Vietnam); (iii) Social: the Choson Exchange based in Singapore is an ideal location for enabling North Koreans to study abroad and thus gain a greater understanding of other countries.