The population living in cities around the world will increase in the next decades. Conventional military forces will deploy more in constrained areas where their high-tech capabilities are not an advantage. This research provides an analytical framework for understanding the main challenges of urban warfare for conventional forces. The analysis identifies the military organizational dimension, dual-use technologies as game changers, and the role of civilian population in urban environments as key factors. The conclusions provide some policy recommendations concerning training and communication strategies. The prospects of urban warfare will be defined by a combination of cognitive and kinetic actions.