Today’s military training environment poses many challenges to instructors, developers, and support personnel. One obstacle is the limited amount of time instructors have to interact with trainees during live training, leading to an increase in simulation in the school house with often high instructor-to-student ratios, dividing an instructor’s efforts across many students. To address this issue, the U.S. Army Research Institute for the Behavioral and Social Sciences (ARI) and SA Technologies, Inc. developed an adaptive training system prototype that provides automated support for instructor-led training through trainee self-guided learning. Using predefined instructor input, the system actively monitors trainees’ activities within a simulation and automatically provides targeted feedback and coaching through metacognitive prompts. These prompts mimic the essential input a live instructor would normally provide, allowing instructors to provide consistent, valuable input to all students while lowering their workload. However, despite a wealth of evidence promoting the efficacy of feedback during practice, such system-based interventions are often regarded as intrusive. The purpose of this paper is to provide an overall review of the constraints and considerations associated with developing and implementing such training systems. This includes a summary of our system evaluation, conducted at the United States Military Academy (USMA) at West Point during incoming cadets’ normal land navigation training, which included classroom, simulation, and live training exercises. Results demonstrated the efficacy of the system for enhancing training with improved task performance both in the simulation and the subsequent live exercise. Additionally, subjective measures yielded positive evaluations for perceived effectiveness of the training intervention, usability of the system, and subjective workload associated with trainees’ interaction with the tool. Together, these findings suggest that the training system and intervention it provides may be a viable approach to enhancing instructor-led, classroom training and provide guidance for the development of future adaptive training tools.