While Service members and their families receive unique financial benefits as a result of their service, few are well educated in the best ways to manage their finances. Consequently, they may fall prey to predatory lending practices, high pressure sales pitches, and other financial pitfalls. Adding to the complexity of this problem is the fact that Service members’ financial priorities change throughout their lives, both during service and after separation. 10 U.S. Code § 992 requires financial literacy training to be provided at specific points in Service members’ careers, including significant life events, at promotion, and in concert with deployments. However, there is no guidance for what specific training content should be provided or when. Further, there is no solution to provide Service members complete access to financial literacy information. Due to the breadth of the financial domain, an effective solution must tailor content to the individual Service member, providing the right information in a timely way, and in an engaging and effective way. Although adaptive training is not a new concept, it is rarely designed to provide lifelong support to learners. Even less frequently are these solutions designed for mobile devices. In this paper, we describe research that designs and develops a mobile Personal Assistant for Learning to support Service member financial literacy. First, we describe the front-end analysis conducted to determine the scope of the domain and identification of learning objectives. Second, we discuss the process to develop a framework mapping the content to specific points in a Service member’s career to enable an adaptive learning experience. We also present research findings to support our approach. Our goal with this paper is to share the process used to design adaptive content to support lifelong learning and discuss lessons learned through our research.