Smart cities embed information and communication technologies (ICT) to create interactive milieus that constitute a bridge between the physical and the digital world. In their attempt to improve citizens’ quality of life through a more efficient use and sustainability of resources, smart cities might, however, also raise important concerns as regards the privacy and confidentiality of personal data flows. Insofar as the design of a city’s telecommunication infrastructure is likely to affect the nature of social dynamics and human interactions, it should, ideally, be achieved through a coordinated, citizen-centric approach combining integrated ICTs with active citizen participation and an intelligent management of physical, digital and informational resources. This chapter analyzes the case of community mesh networks as an example of grassroots decentralized communication infrastructures, whose architecture design has important implications on the deployment and configuration of smart cities.