The incredible growth figures that many Asian countries have realized in the later part of the 20th century, and the growing amount of political power that accompanies it, are unprecedented. This is particularly the case in the ten states that constitute the Association of Southeast Asian Nations (ASEAN), which managed to achieve economic success and peaceful environment in a region characterized by a wide variation of ethnicities with different norms, values, languages and religious beliefs. Indeed, despite the initial scepticism on its durability and ability to play a significant role in shaping the region, ASEAN has proved to be able to adapt to changing conditions in geopolitics and economics, become a stabilizing force in promoting security and peace, and facilitate economic growth amongst its members. The end of 2015 will see the next major landmark in ASEAN integration by initiating the start of the ASEAN Community. However, challenges remain. This paper has found strong support that ASEAN integration has primarily been driven by the desire of state regimes to satisfy political self-interests such as state security, sovereignty and regime survival, influenced by developments in the external environment, which have caused political cooperation to push economic integration in order to ensure economic growth and political stability. These interests have played an important role in ASEAN integration throughout its history, by pushing for integration that is deeper and broader, but also by limiting the progress of region to become larger than the sum of its parts. In order for the relatively small Southeast Asian countries to develop and gain more economic and political influence on the world stage, creating an integrated region is crucial, but the desire to uphold regime survival makes the future of ASEAN unclear. The principle of conflict avoidance has created stability in the short term, but the lack of cohesiveness and unresolved conflicts between the members are able to undermine integration in the future and prevent the Association from gaining a stronger position in the world arena. The reiterated importance of the principles of the ASEAN Way in regional decision-making and the lack of commitment of governments to increase the level of institutionalization show that the willingness to move ASEAN forward is missing. These findings indicate that ASEAN’s character is unique and distinctive from regional integration schemes such as the EU, and imply that comparisons with these other schemes have limitations to predict ASEAN’s future.