Over the last 15 years, Russia has reemerged as a growing power and has sought to exert its influence among old members of the Union of Soviet Socialist Republic (USSR). This is part of a Russian strategy focused on Russia reemerging as a dominant power within the region. When the West threatened Russian interests and Russia viewed the conditions as favorable in terms of being able to achieve its objectives with acceptable levels of risk, Russia utilized controlled escalation of military operations to promote its interests and achieve its objectives. Russia conducted military operations in Georgia, Crimea and the Donbass region of Ukraine as a means of reasserting its influence within the region while simultaneously seeking to reduce the Western influence of the United States, the North Atlantic Treaty Organization, and the European Union within Russias zone of privileged interest. This paper argues that Russia utilized controlled escalation in their operations in Georgia, Crimea, and the Donbass region of Ukraine as a means to manage operational cost and risk and maintain the operational initiative in achieving objectives in pursuit of their interests. There are important lessons the United States and its allies can draw from the Russian operations in Georgia and Ukraine that will inform potential options in countering future Russian aggression.