The urban environment has changed rapidly in the last 200 years, from that of the agrarian or mercantile city, to the industrial, to the post-industrial and emerging digital city. These changes are highly uneven and discontinuous, in parallel with the waves of socio-technical development and the world system of cities. For the future there are many pressures and challenges, and also many different trajectories. On current projections, two-thirds of the world’s population will be urban, and half of these will be residents of informal settlements, lacking fixed infrastructure or welfare systems. Other extremes may exist side by side: we can envisage a new generation of affluent, well-designed, low-carbon cities, alongside fossil-fueled sprawls in vulnerable or hostile climates. We also have to stretch or rethink the definition of “what is the city”: already there is a massive low-density urbanization of peri-urban areas, while floating settlements and tourist city replicas are pushing towards the extremes of virtual cities and exotic urban habitats. Some things appear almost certain, such as the impending chaos of climate change, and the uneven progress of global development. Other forces of change are up for debate, such as the implications of digital transition on the cohesion of social and economic systems. There are fundamental contradictions, between the rhetoric and technical potential for “green and sustainable cities,” and the probable outlook for the urban majority of “brown and vulnerable cities.” All this raises the uses and meaning of future studies and foresight, in a complex and uncertain arena. Urban planning should take a long-term strategic view, but often has to work with short-term tactics and uncertainties. Urban stakeholders can debate the longer future, as a lens on present day fears or aspirations, or to energize and mobilize creative pathways and actions. The urban environment in all this is a green backdrop and capital asset for some, but a source of livelihood or life and death for others. We can perhaps be sure of one thing, that the human dimensions of the urban environment will continue to be challenging and controversial.