In 1974, he attended the five-week-long Squadron Officer School at Maxwell Air Force Base.

He was then a test pilot stationed at Eglin Air Force Base 1978–82, during which time he flew test flights for the McDonnell Douglas F-4 Phantom II, the General Dynamics F-111 Aardvark, and the General Dynamics F-16 Fighting Falcon.

Bolton spent the next phase of his Air Force career in program management.

Also, in 1991, he completed a master's degree in national security and strategic studies from the Naval War College.

In 2002, while serving the commander of Air Force Security Assistance and Cooperation Command at Wright-Patterson AFB, President of the United States George W. Bush asked Bolton if he would step down from that position and accept nomination as the United States Assistant Secretary of the Army for Acquisition, Logistics, and Technology.

According to his wife, Linda Bolton, he stayed in the job for a long period because felt compelled to ensure that soldiers in battle were receiving the best equipment possible.

At the time of his death he was training for the Air Force Marathon, an event he participated in annually with his two daughters.

He will be missed, not only by the students, but also by the faculty, with whom he spent many hours over the last few years, providing assistance and valuable feedback that directly influenced the quality of instruction and the course