The smart city is often approached by its critics as a “system” that exploits optimal connectivity and efficiency for an urban society of control. Meanwhile, the actual operation of “smart city” assemblages in globalizing cities—characterized by development and breakdown, connectivity and disconnection—is seldom the basis of analysis. By focusing on the interplays between these dualities, this article aims to underscore the modalities of power and political possibilities of dissent in Istanbul, Turkey. Data-based smart city apparatuses are supposed to at once fix infrastructural breakdown and stabilize the socio-political order. However, during the Gezi protests of 2013, the integrated tactics of sabotage in urban space and data vandalism in the digital realm undermined both data control by the state and its political authority. Yet Gezi’s example also shows that hyperconnectivity, data motility, and virality by themselves do not necessarily lead to more meaningful participation in urban politics.