The subject of the study is the features and main content of the discussion on the problems of teaching Chekhov's creativity in post-Soviet secondary and higher educational institutions presented on the pages of the information and bibliographic publication "Chekhov Herald" in the 2000s and 2010s. The problem of the need to create new educational and methodological manuals adequate to the post-Soviet socio-cultural situation, as well as the problem of spreading scientific knowledge about the life and work of A.P. Chekhov attracted the attention of leading modern Chekhov scholars, prompted them to create new educational materials, organize special conferences and, in general, to discuss this problem. The discussion allows us to judge both the latest problems and challenges of both academic Chekhov studies (and literary studies in general) and the school practice of teaching Chekhov's work and literature in general. The analysis of the materials presented on the pages of the information and bibliographic edition of the Chekhov Bulletin allows us to see the peculiarities of the dynamics of this discussion and modern Chekhov studies in general. The main conclusion of this analysis is that with the change in the socio-cultural situation from the turn of the 1990s‒2000s to the end of the 2010s, the challenges that the community of Chekhov scholars tried to answer, also changed. At the beginning of the 2000s, the appearance of new textbooks at the same time was accompanied by the problem of their inaccessibility, especially in the provinces; the widespread use of the Internet by the end of the 2000s – early 2010s partially solved this problem, but created a new one: the inaccessibility of high-quality information as the main problem was replaced by a decrease in the level of culture of reading and critical thinking among schoolchildren/students and, often, teachers, a decrease in the general cultural level leads to a widening gap between academic literary studies and school practice and an intensification of the intergenerational cultural gap, attempts by Czech scholars to influence the school study of Chekhov and Russian literature in general face the problem of unpopularity, lack of demand for scientific humanitarian knowledge in society.
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