This article seeks to explore the development of the new security environment in the Black Sea and its implications for the future of regional dialogue between Turkey and Russia. The radically altered strategic balance in the Black Sea after the Russian- Georgian war in 2008 and Russia’s annexation of Crimea in 2014 have urged Turkish policymakers to revise their traditional policies toward this region. Yet Ankara currently faces four main challenges in this quest: i) maintaining the status quo established by the Montreux Convention, ii) protecting its interests vis-à-vis Russia’s strengthened military presence in the Black Sea, iii) dealing with the significant security implications of the three Russian anti-access/area denial (A2/AD) spheres built around Turkish territories, 4) accommodating the diverse Black Sea policies of its NATO allies without alienating Russia.