Daily life in cities is often about balance and compromise. Urban densities facilitate things being in close proximity and provide convenience for residents, but they also create an opportunity for traffic congestion and increased social and environmental inequity, and the possibility of lower-density suburban sprawl. To promote urban sustainability, a careful balance of economic development, ecology, and equity is required. In this chapter, four examples of urban sustainability crises and the dramatic response to them are examined. The cases include Miami, US; Oslo, Norway; St. Georges, Grenada; and Shenzhen, China. In each situation, the sustainability crisis emerges from a deeply set awareness of diminishing environmental quality of life and a feeling that the residents’ sense of place is under threat. The drivers of this threat are deeply embedded in social and economic factors. In each city, the policy switch to enhanced sustainability results from an aggressive, multi-scalar effort to alter and redirect the pattern of urban spatial development.