Simeone and Patelli, building upon their experience as designers and scholars within the Urban Sensing research project, provide materials for scholars and researchers to reflect upon the potential and limitations of social network analysis and data visualization as research methods in urban studies. The chapter starts with a fundamental consideration of the limitations and the distortions inherent in any measurement and technical mediation, considering the particular context of evaluations stemming from quantitative analyses of big data. Simeone and Patelli then map out precursory initiatives and projects that made use of the spatial web to study contemporary cities. Based on concrete empirical examples the methodological limitations and potentialities of Urban Sensing are discussed; which lead to the authors’ reflections on the relevance of sensing the urban through the social web.