Geopolitics is never constant. There are always actors with revisionist ambitions who seek to alter the existing political order with a hope of securing a better position in the emerging circumstances. Presently, the world appears to be traversing one such period of geopolitical reconfiguration, characterized by the rivalries and overt confrontations among several major global powers. These dynamics in international relations, particularly the repercussions of the Russia–Ukraine conflict, have also had implications for the security order of the South Caucasus. Facing an unexpected military debacle in Ukraine and massive economic troubles at home, Moscow has also encountered challenges in the South Caucasus, a region that Russia has traditionally treated as part of its “zone of privileged interests” and dominated its security space. In parallel with the decline of Russia’s regional hegemony, other external actors discern new opportunities to step into the resulting power vacuum in this geographically strategic region. Meanwhile, the three countries of the region – Armenia, Azerbaijan, and Georgia – are strategizing to take the most advantage from the situation, boost their independence, and safeguard their national interests. The developments in regional politics over the last few years signal a significant transition towards a new security order. This article explores the veracity of this ongoing transition and, if it is indeed taking place, what repercussions it might hold for the future of the South Caucasus.