Easel paintings recovered in the last decades in Italy and in the Balkans disclosed surprising evidence about the role of Russia and Orthodox enclaves in anti-Turkish military and ideological mobilization of Christians during the seventeenth and eighteenth centuries. The novelties match the unusual political engagement of Orthodox painters as well as their original responses to the challenges of Italian Renaissance and Baroque, ranging from transformation of themes and compositional designs to upgrading of materials and techniques. In order to elucidate the historic background and the concrete ways of this rapprochement between Western and Orthodox methods, little known testimonies provided by Russian and Balkan archives are compared with the results of technical and technological investigations carried out in Eastern Europe. They demonstrate that the occidentalization of Balkan iconography occurred under the spiritual guidance of the Kiev and Moscow Theological Academies and was technically assisted by the czar painters, while the practical organization was carried out by the Russian monarchs’ agents in Italy: Caretta, Bozis, Beklemišev, Raguzinsky and Orloff.