This article aims to build a bridge between past, present, and future, and to search for the connection between the old urban imaginary of the virtual city, and the new narratives associated with urban platformization. It aspires to recover the utopias and expectations linked to the emergence of digital technologies and the Internet, and the urban changes that were formulated as promises, but also to detect the warning signs and fears that these socio-technological and urban transformations aroused over time. The platform city constitutes the urban manifestation of changes in informational capitalism that affect not only the way of producing and consuming, but also the labor market, social interactions, and human subjectivity itself. Adopting a retrospective view allows us to deepen the analysis of the urban effects of platformization in order to recognize challenges, risks, and opportunities of the current phase of informationalism—among them the limitations for the intervention of local governments in the platform’s governance—and identify the main problematic issues associated to platform urbanism.