Within an Air Operations Center AOC, planners make crucial decisions to create the air plan for any given day. They are expected to complete the plan in part by pairing targeting or collection tasks with the available platforms. Any assistance these planners can acquire to help create the plan in a timely manner would make the entire process more efficient and effective. This paper describes the Intelligent Pairing Assistant IPA decision aid, which provides pairing recommendations at specific decision points in the planning process. IPA is deployed as a plug-in to the Master Air Attack Plan Toolkit MAAPTK software system already in use within AOCs. The primary contributions of this case study are applying artificial intelligence techniques to a novel domain and discussing the software evaluation efforts in moving from a prototype to a deployed system in this high-stakes domain.