The Maneuver Center of Excellence (MCoE) develops doctrine and provides Jumpmaster training. They are interested in strategies to build knowledge retention and improve test performance without lowering performance standards. Students of the Jumpmaster course are required to gain proficiency in airborne operations during a short period of time. In order to meet the needs of the MCoE, the Army Research Laboratory funded the development of a tool for training called the Learning Master (LM). This paper describes a systems engineering approach to the design and development of the LM prototype. The LM system was presented to students in the Jumpmaster course to assess the usability of the application. Finally, the paper discusses potential limitations and presents the path forward to improve the LM application for future use.