Despite more than a decade-long process to transition aircraft maintenance practices from paper-to electronic-based systems, some organizations remain unable to complete this transition. Researchers have indicated that while organizations have invested resources in technology improvements, there remains a limited understanding of the factors that contribute to effectively managing technology-enabled change. The purpose of this case study was to identify and explore socio-technical (ST) factors that inhibit an effective transition from a paper-based system to an electronic-based system for aircraft maintenance. A conceptual model applying theories of change management, technology acceptance, systems thinking, and ST theory informed the research. Thirteen participants provided data via semistructured interviews, field observations, follow-up interviews, other documentation, and a questionnaire. Data were analyzed with open and axial coding techniques to identify themes, which were then crosschecked and triangulated with observation and follow-up interview data. Findings revealed communication issues, a fundamental misconception in training, and a false assumption that all personnel easily acquire computer literacy. Benefits gained from this study should assist maintenance, repair, and overall (MRO) organizations within the Department of Defense to improve current and future technology implementation as the research underscores real-life issues from a comparable organization. The implications for positive social change provide a greater understanding of technology-enabled change and contribute to the development of best practices for technology initiatives that address common ST issues in the MRO workplace.