The uncertainties that are part of the development trajectories of cities challenge spatial planners in designing productive interventions. This paper explores how complexity theory can support planners in dealing with these uncertainties intelligently. It presents a dynamic, time-sensitive understanding of spatial transformations that helps to clarify the interconnected and changeable nature of the underlying processes. The paper continues by proposing an adaptive planning approach that strengthens the responsiveness of urban areas to both expected and unexpected changes. The argument is made that adaptive planning first and foremost implies a focus on influencing and creating conditions for development, followed by attention to content and process. Based on an imaginary case of inner-city transformation, the paper distinguishes key conditions for guiding patio-functional configurations and supporting capacity building of local actor coalitions.