This article examines Azerbaijan's foreign policy by demonstrating the interplay between the oil-led development process and early post-independence regional conflicts that enforced a Western orientation in the country's foreign policy. It is argued that geopolitics continue to prevail in the strategic goals of Azerbaijan. However, the new challenges in the emerging framework of energy security, which extends beyond the revitalized geopolitical rivalries and preeminent concern over securing energy supplies, put Azerbaijan's foreign policy at a crossroads and require a new trans-Atlantic partnership to promote human security and to manage the risk entailed in the unpredictable policy environments of the Caspian region.