Despite the promise of AI and IoT, the efforts of many organizations at scaling smart city initiatives fall short. Organizations often start by exploring the potential with a proof-of-concept and a pilot project, with the process later grinding to a halt for various reasons. Pilot purgatory, in which organizations invest in small-scale implementations without them realizing substantial benefits, is given very little attention in the scientific literature relating to the question of why AI and IoT initiatives fail to scale up for smart cities. By combining extensive study of the literature and expert interviews, this research explores the underlying reasons why many smart city initiatives relying on Artificial Intelligence of Things (AIoT) fail to scale up. The findings suggest that a multitude of factors may leave organizations ill prepared for smart city AIoT solutions, and that these tend to multiply when cities lack much-needed resources and capabilities. Yet many organizations tend to overlook the fact that such initiatives require them to pay attention to all aspects of change: strategy, data, people and organization, process, and technology. Furthermore, the research reveals that some factors tend to be more influential in certain stages. Strategic factors tend to be more prominent in the earlier stages, whereas factors relating to people and the organization tend to feature later when organizations roll out solutions. The study also puts forward potential strategies that companies can employ to scale up successfully. Three main strategic themes emerge from the study: proof-of-value, rather than proof-of-concept; treating and managing data as a key asset; and commitment at all levels.