Modeling and simulation (M&S) is increasingly used for decision support during combat operations: M&S is going to war! One of the key operational uses of M&S in combat is collateral damage estimation (CDE). Reducing undesired collateral damage (CD) in war and in operations other than war is important to the United States of America. Injuries to noncombatants and damage to protected sites are uniformly avoided by our forces whenever possible in planning and executing combat operations. This desire to limit unwanted CD presents unique challenges to command and control (C2), especially for time-sensitive targeting (TST). The challenges begin the moment a target is identified because CD estimates must meet specified criteria before target approval is granted. Therefore, CDE tools must be accurate, responsive, and human-factored, with graphics that aid C2 decisions. This paper will describe how CDE tools are used to build three-dimensional models of potential target areas and select appropriate munitions, fusing, and delivery in order to minimize predicted CD. The paper will cover the evolution of CDE from using only range rings around the target to improvements through Operation Allied Force, Operation Enduring Freedom, and Operation Iraqi Freedom. Positive CDE feedback from various sources, including the Secretary of Defense, lessons learned, and warfighters will be presented. Current CDE tools in the field and CDE tools used in reachback are being improved, and short-term and long-term improvements in those tools and in the CDE methodology will be described in this paper.