Technologies, for example artificial intelligence (AI) and big data, are just two of the innovations that may change the tools and roles of planners. Many of these innovations are becoming embedded in smart city initiatives. This chapter questions the relevance of the predominant tools of planning, planning support systems (PSS), as cities think of adopting smart city initiatives. We compare the evolution of PSS to that of smart cities. Comparisons between changes in PSS and the short history of smart cities show that what constitutes a smart city complicates a path forward in integrating the two. We see potential challenges in the adaptation of PSS, related to concepts of technocracy and opacity, digital divides, wicked problems and the role of civic participation in the planning process. We are particularly concerned with automated systems obviating the need for PSS and planners. We conclude by exploring ways to solve planning problems with AI while remaining cautious about a 1960s-type hyperbole about the smart city.