This chapter focuses on the key challenges facing cities in developing countries. Observations from the case study cities of Gaborone, Santiago and Johannesburg have indicated an overwhelming range and scale of challenges with extremely limited opportunities. Deterioration of socioeconomic, environmental and institutional capacity has been noted as a recurrent trend in all three cities. Equally, prioritization of socioeconomic and local environmental challenges has meant that global environmental concerns have not been accepted as urgent local issues. Consequently, the expectation that, through sustainable development, developing countries will catapult themselves into cleaner technologies (smaller ecological footprint with increasing standards of living) cannot be justified on the basis of the prevailing trends in the case study cities at this point. It is therefore clear that efforts to address sustainable urban development in a comprehensive manner will require many more resources and several times the capacity currently in place within such cities.