It is no doubt that the rise of new energy actors in post-Soviet geographic space such as Azerbaijan, Kazakhstan, and Turkmenistan was welcomed by Western power centers. Those emerging actors were assessed as partners in diminishing Europe’s energy dependence to a single supplier; the Russian Federation. In this context, the main Western initiatives to challenge Russian energy dominance regarding the Caspian Basin were the Baku-Tbilisi-Ceyhan (BTC) oil pipeline, and South Caucasus gas pipeline. These two strategic pipelines pass through the territories of Samtskhe-Javakheti region of Georgia - a tiny administrative unit adjacent to the Turkish city of Ardahan and Armenian city of Gyumri. Because of that, any political turmoil in that strategic region should easily turn into a factor endangering both already unsatisfactory regional stability and European energy security.In this article, Samtskhe-Javakheti region’s economic and demographic characteristics that make it unique and prone to instability are analyzed and European Union’s Samtskhe-Javakheti policy is evaluated through the lens of security of energy supply. The conclusion of the paper is that, the European Union failed to establish influential cooperation mechanisms to avoid political and economic instabilities in this transit region. The European Union simply lacks a comprehensive regional plan compatible with the sociological and economic realities of Samtskhe-Javakheti