The Obama Administration’s desire to push forward with strategic nuclear arms reductions during the President’s second term requires the navigation of numerous shoals and reefs. U.S. and Russian negotiators will have to overcome both political and military obstacles to accomplish post-New START reductions in long-range nuclear weapons. For example, efforts to reduce offensive nuclear weapons are complicated by U.S. and NATO plans for missile defenses deployed in Europe and by exigencies in U.S. and Russian domestic politics. In addition, the military-technical aspects of cyber war and nuclear deterrence can no longer be treated, analytically or practically, as isolated compartments. This article considers several aspects of the relationships among possible post-START offensive force reductions, advanced conventional weapons including missile defenses, and emerging cyber capabilities.