This paper discusses our investigation on the potentials of CAAD system implementation to generate collaborative process in a complex organization of construction project. Housing reconstruction projects in disaster-recovery context has been taken as case study to examine some CAAD system that has been claimed as collaborative. Based on social organizational theory and complex adaptive system theory we attempt too test the claim by analyzing the flexibility of these CAD system on the real complex organizational project. We stratify the result based on the level of adaptability of each CAAD system to indicate the level of collaboration.