This chapter addresses the daunting challenge of urban warfare on tomorrow’s battlefield. In the first section, it provides a brief background of the urban warfare phenomenon. It approaches urban warfare by asking why the field has now emerged after a long period of relative neglect. Thereafter, the chapter outlines the different challenges to and expectations for urban operations on the battlefields of today and tomorrow. A number of key challenges are addressed: the impact of rapid urbanization, multi-domain operations, grey zone problems, the impact of technology on urban operations, and the urbanization of insurgency. Observing that urban areas will be an increasingly important arena for future land warfare, the chapter argues that urban operations and warfare should acquire a greater significance in our understanding of the operational environment. With large cities being the centre of gravity for political and economic interaction and although urban warfare is a nightmare that one reasonably hopes to avoid, it is not always possible to choose the battlefield and it is therefore better to prepare thoroughly for this eventuality. Finally, to help with the preparation, the chapter presents eleven lessons about urban warfare.