This chapter, analyzes megaprojects characterized by processes of high-tech innovation in urban settings, focusing on urban technopoles, manufacturing megaprojects (factories of the future), innovation districts (innodistricts), the pervasive expansion of the smart-city paradigm, and its gradual evolution into a nascent AI urban regime. Such an AI regime is characteristically disruptive, and it begins to show some distinct features that impose valuation and devaluation strategies over entire neighborhoods and urban areas, thus reinforcing marked inequalities and a dual pattern of benefits and high risks in already “quartered” cities. By focusing on high-tech development and utilization, particularly new kinds of automation capabilities and AI, this chapter offers some elements for a critical analysis of the “smart-city” paradigm and the promises and discontents of urban sustainable infrastructure centered on these new technologies. The paradox of artificially intelligent urban environments lies in the promise of attaining a certain type of sustainability at the risk of further jeopardizing urbanity, equality, and livability. AI alone does not necessarily foster urban sustainability, even if specific AI innovations can. Furthermore, in the case of innovations that foster sustainability, one needs to factor in both the benefits and risks of the innovation strategies. The key question is how to craft and build a framework for sustainability that can discriminate and identify which innovations contribute to the desired sustainability outcomes. This Chapter discusses the empirical evidence from five megaprojects in Barcelona, Boston, London, Abu Dhabi, and Toronto.