In Curse Of Strahd, Oleg's entire flock was eaten in a single morning, while he was out collecting stones at Anna's behest. This was noticed by Eugenija Fidatovna, who asked a group of adventurers called Heralds of Dawn to help. A crowd of people was spurred on by Anna to call for Oleg's head, but he was defended by Ghalwin of the Grove and Ajuni Elajoral, who he called "Mr. Man" and "Ms. Angel."
The resulting events ultimately revealed Ilya's true nature, Anna's crimes, and Oleg's innocence, but left the village's future in question. He remained in the care of Eugenija, who took over as interim Burgomaster until the Slaying Of Strahd.