This book bridges media, technocultural, urban, and journalism studies to examine the role of journalism in relation to a smart city project on Toronto waterfront. From the announcement of the public-private partnership called Sidewalk Toronto to the project termination, a mediatized controversy unfolded. Through an assemblage approach to this project and a case study of The Globe and Mail and the Toronto Star, it follows the actors and chronicles the Quayside project story as a conversation about the promise and perils of a future “smart� neighbourhood. In the news of Waterfront Toronto, Sidewalk Labs, other actors, events, and developments, there were multiple voices and views, interpretations and arguments, that manifested conflicting interests and values. As a locally situated actor, journalism produced a porous discourse that expressed a propose-and-public pushback movement. This work of articulating mediation conditioned the project alteration and dissolution within asymmetrical relations of power. In addition to a wave of opposition that inflected the project enactment, a time lag between project time and governmental policymaking made the controversy over this future urban space intractable. With their residual symbolic power, quality journalism contributed to dialogical urban learning.