In this episode Jon O’Gorman hosts David Stone, Timothy Hoyt and Nicholas Sarantakes to explore the question, "When does it makes strategic sense to fight in a city?" We begin by discussing our theorist's opinion about the theory behind the issue, in particular why fighting in cites might or might not make sense from a strategic perspective. We then examine some particular examples, including, among others, Ireland in 1916, Manilla in 1944 and Stalingrad in 1942.