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Planning for combat in an urban environment is a complex task. The urban environment combines the challenge of conventional combat with the complexity of three-dimensional terrain, constrained maneuver space, and a high density of people on the battlefield. The traditional answer to this problem was to rubble the city while defeating the organized resistance found within the urban area. The battles of Aachen, Stalingrad, and Grozny (2000), reflect this rubble approach. However, several factors have driven military thinkers to look for a more efficient and effective manner to defeat an adversary within an urban environment. These factors include a lower tolerance for friendly military and civilian casualties, post-conflict considerations, and a smaller friendly force structure. This monograph describes a possible technique to allow military planners to identify key objectives that may be affected in gaining control of a city without destroying it. This technique involves viewing a city as a complex "system of systems" and offers the planner insights as to where to apply military means to achieve the desired ends. While much has been written on Effect Based Operations (EBO), this monograph attempts to "operationalize" the concept. It presents a planning technique to assist in identifying targets, understanding target interrelationships, and analyzing second and third order effects. This study uses the urban environment to present this planning technique. The primary research question is: Is it possible to seize and control a city without destroying it? The secondary question is: Is there a systems approach process to achieve military success in an urban environment? The purpose of this paper is to provide the operational commander with an approach to manage the complexity of the urban environment., The original document contains color images.