The current generation of junior officers have spent the last ten years continuously deployed with tactical units focused on stability operations for both training and execution. This has led to a significant degradation in Major Combat Operations (MCO) planning and execution abilities at both the tactical and especially the operational-level. Faced with an unclear operating environment and a population of experienced combat vets, the senior military leaders must determine the training direction of the armed services. In a fiscally-constrained environment, web-based learning games can assist in rapidly bridging the gap between the familiar and unfamiliar at a lower cost and at increased adoption rates versus large simulations. This book describes the designing and development process of an original web-based wargame that familiarizes junior field-grade and senior company-grade officers on MCO operations at the joint level. The end state was the production of a completed paper wargame and a VASSAL module which adapted the paper version into an electronic form. Lastly, using HTML5, Javascript and mainly free-to-use tools, we created a prototype wargame that only requires a web browser for service members to play.