The USAF supports US operations in the War on Terror but its struggle to balance these operations with conventional requirements hinders effectiveness and efficiency. This report determines airpower roles in counterinsurgency (COIN) operations by analyzing COIN basics and a century's worth of lessons learned. A comparison of USAF conventional capabilities and aircraft against COIN airpower roles highlights the conventional fleet's shortfalls. The report also assesses the detrimental effects of conducting COIN operations in Afghanistan and Iraq with an aging, conventional fleet, as well as the lack of COIN doctrine for airpower. The recommendation to solve the COIN capability shortfall is for the USAF to supplement its conventional inventory with commercial, off-the-shelf (COTS) aircraft. However, while the USAF needs to change to meet COIN type threats, it does not need to transform into a COIN only air force. Using COTS aircraft would enable the USAF to maintain its conventional capability while simultaneously employing a robust COIN capability. Numerous COTS aircraft are well suited for COIN-type missions, adaptable to the demanding operating environment, and available immediately. Procuring COTS aircraft would enable the USAF to get the right platforms for the necessary mission tasks in a fraction of the typical procurement time and cost.