This paper sets out to examine why it is that combat in urban environments is so deadly and casualty-heavy for conventional militaries, even when those militaries hold a technological and/or numerical advantage. The paper aims to test the theory of Alice Hills through a structured, focused comparison on three cases of urban warfighting. The paper examines the battle of Stalingrad 1942-1943, the battle of Mogadishu 1993 and the first battle of Grozny in 1994. Support for Hills theory is found in what she argues is a pre-modern type of combat that is slowgoing and relies upon ground forces as well as the equalization of technological advantages through improvised adaptation of older and/or less than ideal equipment. The paper highlights the need for intelligence in urban operations, especially human intelligence, as a potentional further development of Hills theory.