The South Caucasus is not only one of the most multi-ethnic regions on Europe’s periphery but also, and probably because of this, one of the most conflict-inflicted territories in the world. Not only did the disintegration of the Soviet Union allow the three countries of the region – Armenia, Azerbaijan, and Georgia – to recover their independent statehood, but also re-ignited the old hostilities between and inside them. During its existence, for over seventy years, the Soviet Union was a major unifying factor in its territories, although not always peacefully, as it blocked nationalist sentiments and separatist initiatives. When it collapsed in the early 1990s, not only did the republics that once constituted the Union gain independence, but also autonomous entities within some of them strove to seize the opportunity and become independent. South Ossetia and Abkhazia warred against the central government in Tbilisi and, in the southern part of the region, another armed conflict broke out between Armenia and Azerbaijan as the former waged a full-scale war to separate the Nagorno-Karabakh region from Azerbaijan. This working paper analyzes the rationale behind the recent breakout of a long-expected military confrontation as well as the new dynamics to the old conflict which has the potential to further aggravate the enmity between two peoples of the South Caucasus.