Military organizations have been leveraging the latest in computational technologies for training for decades, and recent developments in Adaptive Instructional Systems (AISs) are no exception. However, recent reviews of AIS-related research activities across countries of the North Atlantic Treaty Organization (NATO) revealed many challenges, as well as opportunities, for AISs in military training. In light of these analyses, the authors here consider past AIS development efforts for the Canadian Armed Forces (CAF), identify factors in the CAF context that must be addressed to facilitate the adoption of AIS, and propose a roadmap for successful implementation of AIS in the CAF.