It is the purpose of this manuscript to evaluate the existing status of U.S.-Russian cooperation and the prospects for future joint security ventures in the region. In the process, a second related major rationale will be to assess the coalition's successes and failures in meeting the jihadist threat in Afghanistan. To put the Afghanistan Question in perspective, the 1979 Soviet invasion of Afghanistan will be assessed along with the U.S. reaction to it, and subsequent events like the civil war that followed the collapse of the communist government in Kabul, the rise of the Taliban, and its association with al-Qaeda that led to the 9/11 strikes on the Twin Towers and the Pentagon. Special attention will be devoted to the support that Russia provided the United States in the wake of 9/11 and, more recently, its role in advancing U.S. goals in America's "longest war." Toward this end, the performance of the Obama administration's counterinsurgency (COIN) operations will be explored through three scenarios.