This paper identifies impediments to converting military personnel authorizations in non-military essential positions to government civilians, and estimates the potential savings from civilianization in two areas—Education and Training (E&T) and Personnel and Social Services (P&SS)—to be about $530 million in annual savings to the Department of Defense (DoD) over the long run and about $1.1 billion in annual savings government-wide, by converting about 14,200 military authorizations to about 11,300 civilian authorizations. We identified six recurring issues that undermine civilianization efforts: (1) the lack of a consistent methodology to determine military essentiality for specific positions and functions across the Services; (2) the lack of a unified, holistic approach to DoD military and civilian personnel requirements and budget allocations; (3) military Service concerns about losing converted positions when civilians replacing the military personnel in these positions are perceived as “wasteful overhead”; (4) manpower gaps that emerge while executing conversions, where military billets have been civilianized but converted positions have not yet been filled; (5) human resource and management factors beyond cost that affect the decision to employ military versus civilian manpower to perform a specific function; and (6) the critical role of congressional legislation, from capping/constraining civilian authorizations to past prohibitions on conversions in certain career fields.