The relationships between the EU, NATO and Russia are of great significance for all their actors and for regional security more broadly. The overlapping remit of each is complementary, and provides a potentially beneficial way to address current military and soft security concerns. And indeed good progress has been made —formal relationships have been established and there has been some practical cooperation in a number of areas. This progress is particularly impressive when considered in appropriate historical context— i.e. against the backdrop of East-West confrontation. Few would have foreseen such progress fifteen or even ten years ago. However, there is no 'triangle' —ambiguity and contradiction mar all the relationships, which are dogged by a number of conflicting interests. Moreover, although the top leadership of all three entities profess the desire to enhance the relationships, it is clear that a number of constituencies on all sides do not seek similar developments, for a number of reasons. This has slowed cooperation significantly. EU-NATO cooperation therefore remains problematic, and the West's relations with Russia are by no means past some 'point of no return', to the confrontation of the past half century.