Aviation is a major globalizing force for the transfer of people, goods, and power, as well as a tool of positive statecraft. Through intergovernmental and transnational relationships, the United States and European Union have helped countries such as Ukraine and Azerbaijan build capacity – human, technical, and legal – and engage more fully in the global aviation system. These relationships provide Washington and Brussels with avenues of influence and enhance the potential for civil-military cooperation, without the overt provocation of Moscow. This article argues that this form of constructive engagement is not an exclusive strategy for diplomacy, but a long-term investment in the development of Russia’s near abroad.