This article attempts to examine the repetition of verbal synonyms in written texts at the interface of punctuation, syntax, and orthography in Russian. Synonymous verbs in this article are understood extensively, with reference being made to contextually synonymous verbs as well. All the examined examples represent repetitions of synonymous verbs, which are used as homogeneous parts of the sentence and mediated by punctuational (commas and parentheses), syntactic (conjunctions i ‘and’ and ili ‘or’), and orthographic (slash and hyphen) means. The syntactic property of repetition causes mutual replaceability of those components and synonymise verbs whose semantics may differ by their strict lexical definitions. While the most common means to connect synonymous verbs is a comma, conjunctions seem to structure repetition in the best manner. Orthographic means, especially a hyphen, show their functional extension in relation to synonymous verbs, which have not been canonical in Russian orthography and punctuation guidebooks. Repetition of synonyms is one of the characteristics of spoken language. However, it can also be widely observed in written texts. Although repetition of synonyms may not be a desirable phenomenon owing to its semantic redundancy, it helps the speaker/writer to modify, gradate, and formulate his/her utterances. While it is a communicative strategy for the speaker/writer, it may represent a communicative challenge to the listener/reader, who is expected to grasp the meaning of the repeated synonyms.