Air Force leadership has ordered the development of an Enterprise Resource Planning (ERP) system called the Expeditionary Combat Support System (ECSS). Many current jobs and positions will be streamlined, restructured or removed, while some will certainly be created to handle the new requirements associated with ECSS. The structure of the Air Force is certain to change with the implementation of ECSS. The Air Force has used many maintenance organizational structures since its inception in 1947. The focus of this research is to analyze past organizational structures to define key factors that affect organizational change. A case study style methodology was applied to eight periods of maintenance-related organizational change. Strategic initiatives, information and maintenance-related technology advances, change and project management practices were evaluated for relational affect. The researcher found that the strongest relational variables leading to organizational structure change were force-size change, budget change and major conflict occurrence or cessation.