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The paper outlines a collection of impediments and incentives that has been influential in the adoption of automation technologies in the United States Air Force over the last century. I focus on technologies that replace the pilot or reduce his role in the operation of his aircraft. I conclude that pilot-replacing technologies are opposed, while performance augmenting technologies are welcomed as long as they keep the pilot at the center of the aircraft. Pushing towards the automation of aircraft is the desire for higher performance, the huge investment needed to train pilots, and the pressure to gold-plate systems with cutting edge technology. In addition, the adoption of autonomous air vehicles by other branches of the military is encouraging the Air Force to embrace unmanned vehicles to maintain its role as provider of air-based firepower. Against adopting automation are the pilots themselves and their warrior ethos, the desire to include a human in the loop between stimulus and lethal action, and the inertia of almost 100 years of manned flight. This examination of the non-technological barriers to and motivations for deployment of automation technologies by the Air Force can serve as a starting point for investigations into arms control and policy-influencing activities. The impact of these factors can be magnified or mitigated by social changes independent of the technological trends.