Olds had administrative and staff duty assignments at the Pentagon between 1958 and 1962 as the Deputy Chief, Air Defense Division, Headquarters USAF. In this assignment he prepared a number of papers, iconoclastic at the time, which soon became prophetic, including identifying the need for upgraded conventional munitions (foretelling the "bomb shortage" of the Vietnam War), and the lack of any serious tactical air training in conventional warfare. From November 1959 to March 1960, his section worked intensely to develop a program reducing the entire structure of the ADC with the purpose of generating $6.5 billion for classified funding to develop the SR-71 Blackbird. Following his Pentagon assignment, Olds attended the National War College in Washington D.C., graduating in 1963.