Over the last four decades, the US Department of Defense (DoD) has produced several iterations of military doctrine on the operational environments it functions within, and to no insignificant degree, the increasing relevance of “urban terrain” in its doctrine influences how its military branches operate. The history of urban warfighting doctrine is nascent, considering military strategists have historically avoided cities in wargaming. The defense enterprise has become easily impressionable to forecasting of imminent urban conflict espoused by defense think tanks, private contractors, and policymakers, with little to no regard for histories of urbanization and human settlement that would inform their decisions. These institutions have steered the DoD toward an adamant belief that future conflicts will inevitably be in cities. The result of this assumption has permeated everywhere from the creation of new tactics, techniques, and procedures on warfighting in “dense urban terrain,” to massive investments in virtual and augmented reality industries and the makeshift construction of mock cities and villages across the country and its greater territories. Without a specific enemy, the military constructs one, in technical lands that replicate cities and hybridize cultures for foreign policy objectives. Currently, hundreds of purpose-built artificial cities devoted to simulating warfare in urban areas exist across the United States. This work investigates, through representational simulacra and critical counter-cartography, the emergent urbanizations of the DoD’s synthetic training environment and seeks to broaden the field of urbanism to show the influence that urban warfare preparation produces on the built environment.