The countries of the South Caucasus – Armenia, Azerbaijan and Georgia – currently find themselves at a difficult crossroads. For centuries the theatre of competition between the Persian, Russian and Ottoman Empires, post-independence has brought new geopolitical challenges and choices, with new players including the US, NATO, EU and China all jostling for influence. Furthermore, the collapse of the Soviet Union not only led to a rupture between these three countries and Russia, but also between each other. The lasting effect of this has been over two decades of regional political and economic fragmentation. For a number of reasons, the three south Caucasus countries have opted for different post-independence integration projects that appear to point in different directions and may contain the seeds of further conflict. While the main reasons behind the region’s ongoing fragmentation are internal, external players – in particular Russia –continue to play a significant role.