This chapter interrogates the built environment with respect to its compatibility with thick community. Echoing and extending the analyses of Jane Jacobs and Ray Oldenburg, it is argued that much of the urban environment in technological societies – from suburban sprawl to urban renewal high rises – effectively legislates that citizens live as networked individuals. Not only does the coarse graining of these spaces functionally segregate different facets of everyday life, they ensure that social ties are diffuse and single-threaded. Their lack of appropriate density and walkable amenities limits serendipitous interactions and other activities that support the growth of place-based social connection. Moreover, their poor affordances for “third places” such as pubs and cafes limits the sociability of most neighborhoods. Finally, the governance structures of most areas is either weakly democratic, unable to support constructive ways of working through conflict, or not scaled so as to match the physical boundaries of urban communities.