Global urbanization and heat-related fatalities are rapidly increasing, while the full potential of advanced information technologies to mitigate urban heat has not yet been used by city planners and policymakers. Cognitive computing systems (CCSs), which mimic human information processing and reasoning abilities, can transform how cities strategize and operate. In this commentary, we develop a framework and outline future research directions to understand the disconnect between a strategic and operational CCS, which can facilitate an effective interplay between urban policy (e.g., framing alternative policies) and urban technology (e.g., engaging local communities with data generated by sensor networks).