Airpower has been a feature of low-intensity conflict since the beginning of manned flight. Predominantly, airpower has been the tool of the counterinsurgent. This stands to reason, as the government forces have the financial resources, diplomatic connections, secure areas, and large organizations to employ this advanced technology. In a surprising number of recent cases, however, airpower has been the tool of the insurgent. These have often been small operations that the insurgents cannot sustain over time. Nonetheless, insurgent air operations have almost always resulted in strategic effects far beyond the effort required to execute them. The counterinsurgent, however, can anticipate and negate the effects of insurgent airpower by understanding the preconditions required for its emergence and the effects the insurgent is likely to pursue. This paper will analyze four recent conflicts in which the insurgent use of airpower was significant enough to capture international attention. The first of these was the Sri Lankan civil war, in which the Tamil Tiger Air Wing sustained operations in the face of a superior adversary for more than two years. The second case study is of the opportunistic but effective use of airpower by the Taliban as they wrestled to gain control of Afghanistan between 1994 and 2001. The third study will assess Brothers to the Rescue, a Cuban exile group that initially formed to rescue rafters in the Florida Straits but then gained international attention for its efforts to destabilize the Castro regime. The fourth and most recent case study involves Hezbollahs use of drones against Israel between 2004 and 2006. The final section of the paper will identify trends suggested by these case studies and make recommendations to defeat the airpower of the flea.