This paper analyses the evolution of Azerbaijan's position on regional cooperation since its independence. It argues that unresolved conflict regarding Nagorno Karabagh has been constantly defining Azerbaijan's view on regional cooperation. Facing the necessity to resolve its major security issue, while at the same time sustain its independence and build strategic alliances, Azerbaijan developed a multilayered foreign policy. Rich with natural resources, Azerbaijan has skillfully used this asset to become a key actor in shaping regional cooperation, creating alliances with the states with similar foreign policy orientations and security concerns. This cooperation was strongly securitized. As there was little progress in terms of resolution of the conflict, Azerbaijan remained devoted to the alliances and strategic direction of its integration. However, the substance of this cooperation was changing depending on security in the region, the political backgrounds of leaders and economic growth caused by the inflow of oil revenues, affecting the degree and nature of participation in regional organizations and energy policy. Geopolitical changes, which started to be observed after the Russia-Georgia war, such as Turkish-Armenia rapprochement, will have little effect on the nature of regional cooperation, if and while the major conflict preventing the states from comprehensive economic cooperation is separated from the process of reconciliation.