The EU and the USA have not always agreed on Europe’s approach to energy security, particularly Europe’s relationship with Russia. But even when transatlantic interests have converged vis-a`-vis Russia or the Caspian region, mere concurrence has not always been sufficient for producing positive outcomes. By analysing in broad-brush strokes the motivations of the EU, the USA and Russia in four arenas — Russian and Caspian oil to world markets and Russian and Caspian gas to the EU — the contradictions and challenges are illuminated. As this analysis demonstrates, success is more likely when the EU member states are unified around a position and the transatlantic partners agree on both objectives and strategies.