The current economic crisis has lent extra urgency to ASEAN’s efforts at economic integration and raising its attractiveness for trade and investment. This process gained momentum in the 1990s and has made much progress, as reflected in the emergence of a wide range of extra- and intra-regional agreements. However, the effectiveness of this network of arrangements in stimulating trade and investment depends on not just the characteristics of each arrangement but how well they complement each other. This paper addresses these two areas by examining and evaluating past and present initiatives individually and collectively. Findings suggest that the fundamental impeding issues have endured over the years: lack of political will, ASEAN-style consensus-reliant negotiation, and insufficient management in implementing and harmonising of initiatives. Recommendations include agreement design innovation and focus on shared concerns to overcome lack of will, role expansion of the secretariat to monitor implementation through issuance of score cards, and establishment of specialised bodies such as sub-committees and working groups to enhance implementation and dispute settlement.