As the Twentieth Century closes, efforts towards organizing, training, and equipping U.S. airpower assets remain based on the assumption of face-to-face conventional confrontations. This is a comforting hypothesis, as U.S. technological superiority should keep the odds stacked in our favor for decades to come. Air strategists may be overlooking the fact, however, that this very technological superiority may force adversaries to counter U.S. airpower with other than conventional methods. Couple this with the strong possibility that the interests of the U.S. and our opponents will likely be found on opposite ends of the spectrum of war, and U.S. airpower could be in for some surprises. This study analyzes the asymmetric threat to U.S. airpower across the political, operational, and tactical levels of war and examines whether the U.S. has adequately prepared itself to counter asymmetrical measures against its airpower assets. The answers are not reassuring. U.S. airpower is not likely to overwhelming technological capability by increasing friction levels and changing our visions of surgical warfare into an attrition reality. They will attempt to inflict "virtual attrition" as well by changing U.S. targeting strategies and reducing our effectiveness while buying themselves time to attain their objectives. In this respect, U.S. airpower can be strategically defeated.