The COVID-19 pandemic has accelerated the transition of health systems from “hospital” to “city” thanks to smart devices aimed at health promotion through the deployment of ICT in urban contexts. Worldwide, the pandemic has triggered a rethinking of the healthcare system according to the prevention principle, characterized by the usage of advanced technology, which can widely re-orient markets and public action in the field of public and private health services. The chapter will consider the impacts of such innovations and the challenges for the regulatory framework, with a special focus on the Italian context. First, it outlines the main global and EU strategies for digital healthcare. Second, it focuses on the use of smart devices as tools of health prevention. Third, it highlights critical aspects regarding competition and privacy. Finally, the author reflects upon the centrality of the city as a crucial actor for urban health innovation and its upcoming regulatory challenges.