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Contracting in expeditionary operations is not new. What is new is the scope and magnitude of the roles that contracting and contractors play in today’s military operations. Lack of planning and sound contract integration at the strategic level leads to inefficiencies, ineffectiveness, and, in many cases, outright fraud. Annex W, Operational Contract Support Plan, is the overall operations plan for Geographic Combatant Commands and the Services within the Adaptive Planning and Execution System framework. The authors propose an Integrated Planner and Executor (IPE) model for operational contract support and its integration into Annex W and existing war planning systems by congressionally mandating, authorizing, and funding IPE positions within Service structures. The IPE would be vested with the authority to establish, monitor, and manage Annex W.