The U.S. Army must be prepared to respond rapidly to ambiguous and asymmetric threats especially when laws, rules, and regulations do not provide a clear, right course of action. Soldiers are trained to internalize and demonstrate a shared commitment to the Army Ethic, and act in accordance with the legal and moral foundation of the Army Profession (ADRP-1; U.S. Department of the Army, 2015a). The Army’s strong commitment to development of agile and adaptive Soldiers inculcated in the Army Ethic continues during Initial Entry Training (IET), a sub-set of Initial Military Training. In IET, trainees not only learn and are assessed on technical and tactical skills, but also on character – how they live and uphold the Army Values in everyday activity. A key challenge is assessing character in a manner that facilitates Soldier development while also enhancing leader understanding of training effectiveness. This research showcases an assessment strategy and tools developed and tested for capturing and tracking character in Basic Combat Training (BCT), a component of IET. Specifically, trainee responses on peer evaluations and ethical decision-making questions based on videos showcasing the Army Values were digitally captured using audience response clicker technology. An Excel-based tracking tool was also developed to automatically store and analyze assessment data for insights into programmatic trends. A quasi-experimental study was conducted with three platoons as an initial test of the assessment tools. Preliminary findings indicate that instruction and technology interact to differentially impact learning outcomes (knowledge, critical thinking). Technology alone does not promote learning; as such, its implementation must be supplemented with instructional strategies that align with the primary learning objectives and instructor training on how to appropriately harness the tools to support learning. The assessment tool development process, study results, and practical implications (assessment tool integration, generalizability to other contexts) are presented and discussed.