ASEAN was established as a political and security forum and it was only in 1977 that ASEAN started to focus on regional economic integration. After the entry into force of the ASEAN Charter in 2008, ASEAN affirmed the application of the 2004 Enhanced Dispute Settlement Mechanism to resolve disputes arising from the interpretation and application of its economic instruments, including trade. The entry into force of the ASEAN Charter may be considered as the effective beginning of the legalisation of ASEAN. It is therefore not surprising that none of ASEAN dispute settlement mechanisms have ever been invoked because of the relatively short history of these mechanisms. However, it is also possible that beyond the limited time for disputes to develop there exists some pathologies in ASEAN that mitigate against disputes being resolved by any of the ASEAN dispute settlement mechanisms. To date, only two trade disputes between ASEAN states have been resolved by formal dispute settlement mechanisms and in both cases the ASEAN states preferred the WTO dispute settlement mechanism over the ASEAN mechanism. This book chapter attempts to describe the pathologies that exists in ASEAN and also considers the ASEAN culture relating to dispute settlement and management in general.