The aim of the research is to present the main features of the functioning of allegory in the works of 20th-century Russian monastic writers. The paper examines Christian allegory as a specific tropeic phenomenon. The specificity of the use of Christian allegory lies in its orientation toward the culture-forming texts of the Bible; in its fixation in the didactic parts of the text dedicated to the salvation of the soul, spiritual perfection, the need to strive for virtue; in the authors’ appeal to allegorical images with stable interpretations embedded in the culture; in its concentration on allegories that are part of the established allegorical imagery corpus, which formed as Christian literature were developing. The central place in the work is occupied by the study of the representation of ideas important for church writers through allegory, the actualization of Christian meanings. The scientific novelty of the research lies in the fact that it uses theolinguistic analysis to study the works of Russian monastic literature, indicates the stylistic functions of allegory in the ecclesiastical-religious style, and identifies the main features of the use of allegory. As a result, the following has been proved: when affirming thoughts related to the perniciousness of sins, authors resort to Christian allegories, using images of a swamp, abyss, net, thorns, tree branches, spiderwebs; when describing the life of a person and the path of a Christian, images of a ship, boat, sea, storm, and house are used; in reasoning about virtues, images of water, sun, and sky are chosen. There are several stylistic functions of allegory identified in the texts of monastic literature, such as pictorial, syndicating, emotive, prescriptive, meaning-forming, didactic, axiological. The features of the functional orientation of allegory in the works of monastic literature are as follows: the use with didactic religious-Christian goals, i.e., aversion from sin and encouragement to acquire virtues, strive for the salvation of the soul, moral perfection, spiritual alertness, and the cultivation of the inner person.