All too often, military operations are planned and conducted without a clear understanding of the political endgame expected to occur on the adversary’s side, or by simply assuming rational calculation. Clausewitz states that war is the continuation of policy by other means, yet policymakers do not always articulate how they believe military operations will lead towards the desired political end state. Instead, the end state is left in military terms; with the result that military operations can achieve every stated objective condition, yet the policy aims remain unfulfilled. This is a two-part problem, one theoretical and one practical, and both are interlinked, The theoretical problem is the lack of a mental framework tying the desired end state (usually broadly stated) to the activities undertaken with the instruments of national power. This is a “theory of victory,” which describes how the instruments, properly utilized, have effects which lead to reactions and ultimately to particular political endgames within the adversary’s political system. The practical problem is tracking the many activities contained in a plan to establish that they have some logical linkage to the ultimate end. Military plans are immense. The implied logic behind every activity is not always obvious, and it strains credulity to believe that planners can be sure they are not working at cross-purposes. Yet, just as planners must do the thinking, surely tools beyond word processors can be provided to help them with mindless task tracking. This thesis establishes a theory and tests it against the real word, ties it to a practical tracking methodology, and examines one possible means to assist planners in examining the logic they express.