This book discusses Russia's policy on Crimea influenced by its policy towards separatism in Georgia. By applying concept of political learning, this paper aims to analyse how Russia's learning about its policy to militarily support Abkhazian and South Ossetian separatists in Russo-Georgia War underpinned its policy to more peacefully support Crimea separatists. Based on library research, this paper explains Russia's external and internal environment during Crimean crisis, observation on Georgia-Russo War, belief change, transformed policy and its effectiveness. This paper has found that Russia assessed its operational failures in Russo-Georgia War leading its belief to change that to balance and adapt with external and internal environments namely NATO and European Union enlargement and re-surge of domestic dissents respectively Russia had to win war with more accurate tactics and minimum casualties in Crimea. This change was implemented into non-military measures effectively strengthening Russia's regional leverage, Black Sea Fleet and domestic nationalism.