This work examines the complex dynamics of Russia’s relations with the Caucasus. Beginning in 2000, Putin’s Chechenization strategy had unforeseen and controversial results for the entire Russian Federation. These are elucidated in case studies of the Stavropol region, the Sochi Olympics, the Pussy Riot conviction, and Russia’s efforts to reintegrate religion with politics against the backdrop of an emerging Islamic “inner abroad.” Neither Russia nor the Caucasus can be understood without an appreciation of their uneasy interconnection and its explosive consequences.