One of the most significant tests of U.S. President Barack Obama's tenure has been the U.S.'s relations with Russia. Obama inherited some unwelcome baggage due to the deterioration of relations following the crisis in Georgia. The missile defense system and the debates about the deployment of the radar systems and missiles in Eastern Europe, including the Czech Republic and Poland, also contributed to the significant tensions in bilateral relations. There is a growing mistrust between the two countries and the political actors on both sides have failed to resolve this problem.In the first days of his presidency, Obama signaled a different approach in dealing with Russia. The word "reset" became the key term to define a fresh start in the relations between the two countries. The U.S. not only sent signals but also started to take very important steps in order to repair relations between the two countries. In the meantime, Obama also improved the warm personal relations with Prime Minister Dmitry Medvedev. Despite the lack of chemistry between Russian President Vladimir Putin and Obama, the U.S. administration insisted on pursuing a policy of engagement with the Russian government. As a result of this new policy, both sides took essential steps towards further cooperation. Obama, in a very controversial decision, suspended the U.S's missile defense systems program and the parties launched new nuclear negotiations. Even the spy crisis was handled relatively smoothly between the two countries. Later, this policy opening was criticized, not just for being overly optimistic but also because it miscalculated Russia's decision-making process. Although they reached a nuclear treaty and decided to continue working on issues of international security, including terrorism and Iran's nuclear program, the fact that the U.S. chose to deal with Medvedev and ignored Putin created problems between U.S. and Russian policy-makers. The most significant point of this issue was seen during the open mic crisis in which Obama asked Medvedev to show "some more flexibility" before the elections. Medvedev told him that he would convey the message to Vladimir Putin.Domestically, the "reset" had significant political costs for Obama. It made some members in Congress skeptical about rapprochement between two countries. During the presidential election campaign, the issue became a critical one, as the presidential candidate of the Republican Party, Mitt Romney, harshly criticized the policy. The suspension of the missile defense program in particular generated significant criticism from Congress and the Republicans. (It was not a coincidence that Romney made a stop in Poland during his foreign trip and gained a lot of support from Polish policy-makers.) However, Obama and his foreign policy team usually mocked the criticisms and retaliated in turn by making fun of the Republicans for being stuck in a Cold War mindset.Following Putin's re-election to the presidency, relations never reached the "reset" stage again. The rhetorical tension between the higher authorities of the two countries gained new heights after retaliatory legislation. Obama signed the Magnitsky Bill while Putin prohibited the adoption of children from Russia. In the meantime, the two countries' stances regarding the conflict in Syria began to diverge. Although they continue their diplomatic dialogue in multilateral meetings, the fact that the Russian government was militarily helping a regime the U.S. considered illegitimate generated significant strain. The deterioration of relations continued with the Edward Snowden affair and led to the cancellation of a summit meeting between the two presidents. However, the greatest period of tension took place during the Ukrainian crisis. Ukraine had become a source of crisis before between the two countries, during the Orange Revolution. But this time the crisis turned into a major conflict. At each and every step the tensions between the two countries escalated. Support for the separatist forces from the Russian government, the downing of Malaysian airlines plane MH17 over Ukrainian airspace and the annexation of Crimea deteriorated the situation for both countries. The U.S. adopted sanctions alongside other governments. In the meantime, Putin began to talk about a "nuclear conflict" and the Russian Air forces started to violate the airspace of European countries.The Syrian crisis and Russia's military involvement therein signaled another major step in the escalating strain between the two countries. Although Obama recently stood very much opposed to the idea of Russia gaining an advantage in Syria as a result of U.S. inaction, there are many others who argue that Russian military involvement in the Syrian crisis represents a game changer in the regional politics.So, now, while President Obama is entering his last year in office, he has a Russian file more complicated than the one he inherited seven years ago. Over that time, Russia has militarily engaged in two countries and changed the map of Europe by force for the first time since the end of World War II. The problematic relations between Obama and Putin are unlikely to be fixed in the next 12 months. Although there is a growing common threat, namely, DAESH, which might force the two sides to coordinate operations and cooperate, the damage, disappointment and dysfunction of the last seven years will be hard to ameliorate in the next year. The issue of Russia has already become a topic in the presidential debates and seems as if it will continue to be an issue domestically. So it looks like Obama will pass the presidential torch over to the next incumbent burdened with a more complex Russian file and the issues in relations with Russia will be a significant feature of Obama's legacy.