This chapter traces the complex and tense relationship between Tolstoy and the Russian Orthodox Church. It provides basic background information on the role of the Church in Russian history and in Tolstoy’s time. It reveals that even as Tolstoy rebelled fiercely against the Church, it was the rebellion of a man who was deeply immersed in Orthodox thought and practice; as such, his rebellion itself was colored by the Church. Similarly, representatives of the Orthodox Church found it necessary to publicly respond to Tolstoy’s challenges to Orthodoxy in order to demonstrate the importance of the Church in modern times. Thus, Tolstoy and Church representatives shaped their systems of thought in discussion (and conflict) with each other.