The initiative of New Strategy Center Romania alongside the partner organization, World Experience for Georgia represents an innovative input to strategic awareness and anticipation, an attempt to horizon scanning in the sophisticated security context in the region. The purpose of analyzing Black Swans has bigger stakes than ever, especially after the events during and after the illegal annexation of Crimea in 2014, showing that the Black Sea region and the Balkans have a significant potential for strategic surprises. Given its aim to analyze “Black Swans” on NATO's Eastern Flank, the project seeks to provide a set of scenarios for two of the most vulnerable areas of Europe, notably from the perspective of the countries situated in these regions.