The expansion of multinational pipelines for the transportation of oil and gas has created new opportunities for both cooperation and competition, with implications for stability and prosperity in the wider Black Sea-Caspian basin where the protracted conflicts in Abkhazia, South Ossetia, Trans-Dniester, Donbas and Nagorno-Karabakh have exacerbated mounting dangers to the regional security situation. The two regions comprising the five Caspian littoral states and the six Black Sea coastal countries have become crossroads for increased commerce and economic development as the old Silk Road is revived. Although each of these countries is trying to evolve its own strategy to confront the issues at hand, there is a lack of comprehensive understanding of the need to address energy security challenges from a regional perspective. It is believed, however, that mutual economic gains can reshape regional mindsets, which, at present, get in the way of tackling the most serious disagreements. Public debate on the commercial value of peace can help the political elite promote confidence-building over intra-regional fractures. Boosting regional cooperation in the energy sector and adopting resource-centered strategies for the management of related natural resources can enhance energy security for the whole region so everybody can win. This opinion piece applies post-conflict scenario planning to the future of the regional energy security cooperation in the Black Sea-Caspian basin and describes collaborative steps that could be taken by all relevant players to think more deeply about promoting the integration of energy markets in this part of the world. Overall, the article examines possible ways the post-conflict energy security cooperation scenarios could contribute to shaping conditions that allow political leaderships to consider negotiated compromise solutions to intractable problems.