The 22nd Winter Olympics in Sochi, Russia, possess a singular symbolic character for Russia and its leadership. President Vladimir Putin considers the Games a demonstration of Russia’s growing international role and the success of his administration’s policies. Many view a successful Olympics as integral to his presidency. But also Sochi presents a number of challenges as an Olympic host city. It stands at the center of a number of thorny issues with geopolitical and security implications, including the turbulent insurgencies in the North Caucasus, ethno-political issues such as the “Circassian question,” and the Russia-Georgia-Abkhazia security triangle. It is also a focal point for many nonsecurity issues, including the environment, transportation, housing, and public services. By placing Sochi within the domestic political, regional, and geopolitical contexts, this report examines the myriad challenges facing the Sochi Olympics that could affect the Games. It also examines Russia’s policy response to these challenges and its preparations for the Games, as well as the work that still needs to be done.