Distance learning technology provides the capability to reach multiple, distant, and geographically-dispersed locations with high-quality, real-time instruction. Interactivity improves comprehension and serves as a catalyst for effective learning when coupled with competent design and multimedia. This paper discusses combining the promises of distance learning and interactivity as the basis for an automated prescriptive assessment process. Participants in the United States Atlantic Command's UNIFIED ENDEAVOR exercises attend a relevant curriculum of seminars. They arrive with varying knowledge and experience levels in the processes and procedures associated with the effective functioning of a Joint Task Force Headquarters staff. An automated assessment process will determine individual needs and prescribe tailored curricula and courseware products. Properly focused interactive multimedia courseware can significantly enhance the effectiveness and efficiency of distance learning to meet training requirements.