Singapore‐Indonesian investment cooperation in the Riau islands forms the key part of an initiative in cross‐border cooperation including Indonesia, Malaysia and Singapore. Four flagship projects – Batamindo Industrial Park, Bintan Industrial Estate, Bintan Beach International Resort, and the Karimun marine and industrial complex – are a key test of the effectiveness of a development strategy that seeks to ‘fast track’ development by creating enclaves of investment, protected from the diseconomies and constraints of their surrounding environment. This paper evaluates the progress of the flagship investments and their interaction with their surrounding communities. It shows the constraints on securing enclaves of investment opportunity in the midst of poverty and high population growth. Lessons from the development experience are linked to the political processes affecting cross‐border cooperation in Southeast Asia. This discussion reveals the retention of interstate processes predicated on the continued existence of strong nation‐states, rather than trans‐state processes which permit the weakening of national sovereignty. The negotiating pitfalls and development dilemmas emerging in this political context are identified.