As President Barack Obama enters his second term, relations with Russia present him with a set of thorny problems. The first-term “reset,” a fresh American posture toward the Kremlin that was designed to build productive relations by offering compromises on a range of political and geostrategic issues, has clearly run its course. The Obama administration had partly based its hope for improved ties on the ability of Dmitry Medvedev, who served as Russia’s president from 2008 to 2012, to achieve liberal reforms, especially on freedom of expression, the rule of law, and the ability of civil society to function without state intrusion. However, substantive reforms never materialized, former president and then prime minister Vladimir Putin remained the dominant force in government, and Russia moved abruptly in a more repressive direction following his return to the presidency in May 2012.