Modern lifestyles demonstrably influence language as a social construct. The Russian language is not exempt from the constant evolution of its lexical units; some terms lose their original meanings and acquire new ones, while others become obsolete, replaced by newer vocabulary. Certain situations may necessitate deviations from established linguistic conventions, potentially creating legal grounds for subsequent litigation. The purpose of the study is to analyze some challenging issues of spelling and using words in the Russian language that are reflected in judicial practice. The present study was carried out based on traditional general scientific methods (analysis and synthesis, etc.) and methods of legal science (system analysis, formal-legal, etc.). Analysis of regular and irregular spelling and using words, including foreign ones, in the Russian language tellingly reveals the complexity of linguistic issues facing courts. Notably, challenges arise from the lack of a unified legal and linguistic definition of the word “obscene”, hindering its subsequent legislative consolidation, and from misuse of technology in drafting court documents, leading to repeated mistakes. It is concluded that it is necessary to expand the List of grammars, dictionaries and reference books approved by Order of the Ministry of Science and Higher Education of the Russian Federation No. 195 dated 8 June 2009, containing the norms of the modern Russian literary language when used as the state language of the Russian Federation, including because of the need to legislatively consolidate the new vocabulary appearing in the reference literature.