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Development plans are central tools in spatial planning practice. They create a vision of how places should develop and prescribe how desired patterns of development will be realized. However, development plans are increasingly regarded as inflexible and even rigid when confronted by changes in their context. Conceptualizing urban districts in terms of complex adaptive systems (CAS), this paper identifies ways in which more flexible development plans can be designed. This is investigated through a case study of a development plan for Blauwestad in the Netherlands, which enabled sources of rigidity to be analysed. The paper concludes with the view that from a CAS perspective, development plans are part of the structures necessary to facilitate self-organization, and if designed with certain principles in mind, can play a key role in assisting the endogenous evolution of spatial developments.