Public and private investments are increasingly being directed towards the development of ICTs for the construction of more inclusive and connected communities. Labelled as Collective Awareness Platforms (CAPs) under the European Seventh Framework Program, these initiatives explore the possibility of tackling societal issues relying on digitally-mediated citizen cooperation. As their diffusion increases, it is important to critically reflect on the extent to which they can effectively trigger forms of engagement and sustainable collaboration within and through digital artefacts. Among the associated risks is the furthering of a technocratic understanding of how collaborative processes work, based on the assumption that the introduction of CAPs would be a sufficient condition for the construction of inclusive and engaged communities. In this respect, this contribution investigates a case in which a digital platform was implemented with the aim of promoting citizens’ deliberation on urban-related issues. This experiment is analyzed by 1) assessing whether the platform functioned as a deliberative space; 2) tracking the negotiation processes of the digital artefacts’ functionalities occurring among initiative’s organizers, platform developers, and participants. The goal of the paper is to understand how different understandings and unexpected usages of the digital platform affected the deliberation process and therefore the initiative’s outcomes.