Since the start of the Arab Spring, Russia has sought increased influence in the Middle East, rekindling relationships and building influence in Syria, Turkey, Libya, Israel, and elsewhere. The return of Russian influence puts pressure on U.S. interests in the region. In the increasingly complex security environment of today’s world defined by transregional and multi-functional challenges across all domains, the United States is constrained in the Middle East by both available resources and an American public exhausted by military efforts in the region. America must make difficult choices and prioritize efforts. This article analyzes Russia’s strategy in the region, framed by the ways, means, ends, and risk models, to uncover risks to the Russian strategy that the United States could exploit.