This essay investigates the similarities between Steiner’s and Ga­da­mer’s views on “understanding as translation”, since both thinkers were par­tic­ularly in­ter­ested in the case of so-called translation-from-within. The main aim of this essay, how­ever, is not to discuss how Gadamer and Steiner addressed the problem of trans­lation per se. Instead, by starting with the assumption that, for both thinkers, trans­lation serves as a category to depict the complexities of understanding, my objective is to demonstrate how similar their ideas are con­cern­ing factors which either revolve around the act of understanding (cir­cu­lar­ity), or determine its speci­fici­ty (historicity). My analysis shows that both Ga­damer and Steiner devoted much attention to the impact of history on a human being’s interpretation of certain frag­ments of reality and to the di­a­log­i­cal interaction with texts (broadly understood), this being a specific form of her­meneutic conversation which proceeds according to the interpretive cir­cu­lar­ity specific to the hermeneutic tradition. The connection between Ga­da­mer­ian and Steinerian thought may serve as an important clue to the un­derstanding of the philosophical systems of the two thinkers, in particular their views on trans­lation characterized as the act of intralingual communication, an issue which still remains significantly understudied. These findings may also prove use­ful for the development of translation theory, especially its hermeneutic dimension.