In the U.S. Army Learning Concept for Training and Education 2020-2040, the Army recognizes the need for training/learning management improvements in order to enable education-based learning (U.S. Department of the Army, 2017). A mobile assessment tool called MLC SPOTLITE was developed for instructors of the Master Leader Course (MLC). This paper examines the usability and utility of MLC SPOTLITE as well as lessons learned from implementing new technology in the U.S. Army. MLC SPOTLITE was iteratively developed with input from and testing by MLC instructors, and was deployed on two-in-one devices. The development of MLC SPOTLITE aligned with several factors identified in previous research as facilitators of the use of technology to support the Army Learning Model, including an extensive front-end analysis, subject matter expert support, and editable software (Barnieu et al., 2016). The system streamlines the traditionally paper-based assessment process and allows instructors to digitally complete and sign course rubrics, and easily toggle between students. The majority of instructors found the system easy to use (94.8%), and all instructors agreed or strongly agreed that they felt confident using the system. Despite the need for such technologies to improve learning and education, there are significant challenges associated with using mobile devices in an Army setting. One challenge with using mobile technology is the variable access to Wi-Fi in Army classrooms. This paper explores and discusses some of the barriers that may prevent the wide-spread adoption of easy-to-use technologies. Without implementing mechanisms for overcoming such barriers, the role of technology in fulfilling the Army Learning Concept vision may be limited.