Cities' complex man-made terrain, the presence of civilian populations and infrastructure to support those populations, a complicated information environment, and a range of political and other factors make planning for brigade and division urban operations extremely difficult. Too often, militaries rely on a limited set of options—such as the deliberate assault or an effort to bypass cities completely. But history yields lessons on how to overcome the unique challenges of urban warfare. Chief among these lessons is that developing operational approaches to major urban areas requires planners to account for unique, environment-specific considerations. In this episode, Dr. Jacob Stoil—the chair of applied history at the Modern War Institute, an associate professor of military history at the US Army School of Advanced Military Studies, and a senior fellow at the 40th Infantry Division Urban Warfare Center—explores these considerations and details several operational approaches for brigades or divisions in the offense, drawing on historical case studies to illustrate their value.