In this post-war period, and in the wake of its gains in the Second Karabakh War, Azerbaijan is in the process of pursuing ambitious infrastructure and connectivity projects spanning the transport, energy, and digital spheres. However, such projects face significant geopolitical complications, with a number of players, both in and beyond the South Caucasus region, acting to challenge Baku’s plans. The purpose of this paper is to examine the opportunities and constraints that Azerbaijan faces in pursuing its regional connectivity ambitions. The paper concludes that, for Azerbaijan to advance its goals, careful geopolitical manoeuvring is required that focuses on the functional and mutually beneficial gains of building regional connectivity and mitigating the propensity towards division and zero-sum conflict in the Caucasus.