ASEAN transport connectivity is critical to the completion of the ASEAN Economic Community. Cross-border transportation development helps to lower trading time and transaction costs, therefore facilitates the regional economic integration. ASEAN Member States initiated two regional land transport projects: the ASEAN Highway Network project and the Singapore-Kunming Railway Link. The implementation of regional transport projects requires involvement of various stakeholders, but the disparity of funding capacity of individual states is likely to cause collective action dilemma. Regional development banks and donor countries have provided financial sources for the projects, but their contribution remained limited. This research suggests that the main obstacles are the lack of focused mechanisms on transport development, weak project coordination, and overemphasize of ASEAN-way diplomacy in ASEAN. Consequently, different national priorities bottleneck the least developed countries to utilize donors’ funding, and thus slowed down the implementation of regional transport networks. All these make not only the realization of the project but also the completion of ASEAN Economic Community very difficult.