The paper explains the difficulties that have been emerging for the Southern Caucasus regarding these countries’ relationship with and towards the EU. Through the deconstruction of the area’s particularities and specificities, and its framing in the EU’s policy to the region, this paper aims at analyzing the implications of the transition efforts and stability in the area for Europe in general, along with the different roles each of these pieces – Armenia, Azerbaijan and Georgia – play in the complex strategic Caucasian puzzle. Thus, the EU’s neighborhood policy goals are closely interconnected with the principles defined in the Union’s security strategy, demonstrating the commonly felt need for the building of stability in its vicinity as a way of promoting and expanding security.