The U.S. has reached a crossroads with its policy regarding assassination. Executive Order 12333, which explicitly and absolutely prohibits assassination, is still in effect. The ban, however, has been diluted and circumvented since its inception. Past administrations have targeted enemy leaders with "indirect" strikes such as the 1986 attacks against Libya and the 1998 missile strikes in Afghanistan and Sudan. Currently, the U.S. deliberately targets individual enemies, whether in the context of an armed conflict, such as Afghanistan or Iraq, or in the war on terror, such as the November 2002 Predator Hellfire missile strike in Yemen. This ostensibly duplicitous policy has caused controversy for the U.S., both internally among policy makers, military leaders, operatives, and the American public, and externally with the international community. This thesis examines U.S. assassination policy in detail, and proposes recommendations for modernizing the Executive Order. The intent is to provide decision makers with a clear point of reference, and a framework for determining when assassination is the best-or at a very minimum the "least bad"-possible option for dealing with the complex and dangerous threats of modern conflict.