The paper presents an analysis of the final stage assignments developed for the Russia-wide Olympiad in the Russian language for school students. The study identifies assignment types. Etymology and issues of the history of the language receive particular attention in designing such assignments. It is noted that participants are required to combine their knowledge of all Russian language course sections to complete most assignments rather than simply reproduce the material. The research highlights the main problems that students encountered when doing the assignments. The insufficient formation of reading literacy skills and decreased attention to studying and assimilating the language and its levels as systemic phenomena are among such challenges. At the same time, we conclude that many school students demonstrated a high level of language proficiency and general erudition.