Over the past decades the term compliance has become increasingly widely used globally, making its way into national languages. The same is true for Russian academic discourse were compliance (or its Russian analogue “комплаенс”) has become common in a number of areas ranging from business and law to healthcare. This trend as well as cultural practices of revitalizing the social role of religion, which can also be viewed as a form of compliance, substantiate the relevance of this study. The word compliance with the meaning of agreement, accordance and self-restriction has been known in the English language since the 13th century. During the Reformation it notably referred to agreement with people of other beliefs. The purpose of this study is to trace the use of the term and describe its functioning today by analyzing forms corresponding to compliance, especially those with religious connotations. The following goals are set: 1) to describe the linguistic and etymological peculiarities of compliance in various cultural contexts and to specify the grounds for its understanding as a broader concept; 2) to trace the transformation of the concept from religious to secular and to compare personal and group identity markers; 3) to identify the specifics of the cultural practice of compliance as voluntary consent of group and personal religiosity on the example of creative writing; 4) based on texts by A. P. Chekhov to establish the features of the modern cultural optics of compliance in relation to the cultural phenomena of the past; 5) to highlight the key features of reading the works of A. P. Chekhov from the perspective of compliance. The research materials include data from dictionaries and encyclopedias, the linguistic database National Corpus of the Russian Language and selected works by A. P. Chekhov. The work, based on anthropological, axiological, and hermeneutic approaches, uses the methods of discourse analysis and narrative analysis, as well as the biographical method. The return to the broader meaning of the concept of compliance is associated with the peculiarities of the current cultural situation, requiring special attention to the coordination of both secular and religious aspects at group and personal levels. Firstly, in Russian this is fixed by referring to the English term compliance, which goes back to the Latin word complere. Secondly, the conceptual apparatus for describing and understanding religion has been historically developed as a series of forms representing normative aspects of the religious (confessional) identity of the elites of a particular historical period in a particular geographic region. Folk and authored interpretations have been relegated to the realm of marginal superstitions and heresies for thousands of years. Thirdly, the so-called Age of Magazines and Writers opened up new possibilities and ways of representing the deepest experiences of an individual author in literary work that connects the individual with the universal, the intimate with the public, and the instantaneous with the eternal, sometimes giving rise to works that receive worldwide recognition (A. P. Chekhov). However, reflection on this process has become possible relatively recently; Finally, by using the example of the works of A. P. Chekhov, to review compliance of literature and religion in a writer’s work, it has allowed us to highlight the specifics of his artistic realism, based on the techniques of mirror image, and inscribing the conventional magic of personal writing in the time of the religious understanding of culture. As a result, the conclusion is substantiated that the globally recognized work of A. P. Chekhov can be interpreted as an example of the presentation of religion as living religiosity, i.e. the universal social and personal phenomenon of constructing successful practices of supervising the unknown (N. Luhmann), forming historically special institutional and vernacular forms of their unique personal experience.