The annexation of the Land of Smolensk by the Grand Duchy of Lithuania in 1395 had a great impact on the situation of the ecclesiastical officials of the Orthodox Church in this region. The article investigates the development of the careers of the ecclesiastical officials of

the Land of Smolensk when the region was part of the Grand Duchy of Lithuania (1395–1514). The focus is on the origin, kinship, and positions of the ecclesiastical officials, their connections with the central government of the Grand Duchy of Lithuania and with the inhabitants of the Land of Smolensk. Systematised data about the ecclesiastical officials of the Land of Smolensk is presented in the Appendix.