Throughout the nineties, the South Caucasus was a distant neighbour for the EU. However, because of pressures resulting from the EU's eastern enlargement which consumed most of the Union's energy in that very same period, EU thinking on the South Caucasus has changed. The aim of this chapter is to explain this flux in EU's policies towards the South Caucasus through the concepts of structural stability and short-term conflict prevention, terms borrowed from the Commission's conflict prevention lexicon. Employing these two concepts, the chapter explains the motives and the extent of EU involvement in the South Caucasus in two periods demarcated by the 2004/2007 big-bang enlargements. After comparing the EU's role before and after the eastern enlargement, this chapter suggests that the EU is becoming more powerful as a structural stabilizer dealing with the problems of the region at the grass-roots level, more so than as a security actor assuming direct roles in the resolution of the regional conflicts in Abkhazia and South Ossetia.