This article analyzes the blogs of Russian-language Orthodox priests on the platform of LiveJournal. com, focusing on how bloggers reflect on their own activities, how they manage their identities, and how they relate to the secular Other and to the Church hierarchy. The analysis draws on the medieval Russian tradition of “holy foolishness” as the context which helps bloggers orientate themselves in and make sense of the digital environment, associated with a threat to the Orthodox ethos and theology. The article argues that Orthodox bloggers are a closed circle, opposed to the secular “outside world.” In relation to the Church authority, their position is ambiguous: they simultaneously distance themselves from the task of carrying out the Church mission online, and capitalize on their spiritual status for the purpose of “creation of the self” in the digital age.