This book bridges media, technocultural, urban, and journalism studies to examine the role of journalism in relation to a smart city project on Toronto's waterfront. From the announcement of the public-private partnership called Sidewalk Toronto to the project's 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 proposeand- public pushback movement. This work of articulating mediation conditioned the project's alteration and dissolution within asymmetrical relations of power. In addition to a wave of opposition that inflected the project's 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.