The 44-day Karabakh War seriously affected the international balances in the Caucasus in terms of security, politics, and economic dimensions. The attitude of international actors during the war was important to define the fate and consequences of the war. Among these international actors, Russia’s attitude was of special importance. The policy followed by Russia during and after the 44-day Karabakh War had four main and parallel pillars: The first pillar of Russia’s policy was maintaining the status of its traditional ally Armenia. The second pillar was maintaining its mediator role for the resolution of the conflict. The third pillar of the policy pursued by the Kremlin was not harming the strategic partnership relationship with Azerbaijan, which had been specially developed during Vladimir Putin’s tenure. The fourth pillar of the policies pursued by Russia was not disrupting the multidimensional profound relationships with Turkey, which had advanced in recent years. The first two dimensions of this policy followed by the Putin Administration during the 2nd Karabakh War represent Russia’s conventional Caucasus policy and the last two dimensions embody a policy change.