Scholarship in the field of Medieval Studies on the topic of translation between Latin and the vernacular languages has, in general, been plagued by certain overarching narratives and biases. More specifically, at a macro level, translation in the Middle Ages has often been viewed in terms of a cultural struggle between Latin and vernacular literary cultures and thus reifies existing assumptions about the nature of the relationship between Latin and the vernacular languages as one that is fundamentally antagonistic and competitive. The overreliance on such narratives, in turn, has lead to an overemphasis on the role of rhetoric in structuring specific translations (to the exclusion of other areas of Medieval academic thought) and further fails to adequately account for medieval texts that present themselves as translations of a particular source text but that nevertheless do not pursue faithfulness to the same degree as modern translations.Rather than offering an overarching theory about the nature of translation in the Middle Ages, the present study seeks to reexamine and ultimately deconstruct the existing scholarly narratives on the topic of medieval translation and ultimately does so via the expansion of the discussion from simply “translation” to the somewhat broader semantic field of “retextualization,” which allows for the incorporation of works that are difficult to encompass within the traditional paradigm. By exploring three specific moments of medieval retextualization—Notker’s 10th-11th century Old High German translation of traditional Latin school texts (including of the Latin translation of Boethius and Aristotle), the macaronic Latin-Middle High German compositions within the 13th century Carmina Burana, and finally, the 13th century Latin and 14th century Middle High German translations of Mechthild’s originally Low German Fliessendes Licht der Gottheit—the current study applies a discourse-analytic approach that examines the specific texts both in close dialogue with each other as well as in terms of the larger cultural and literary discourses with which each retextualization engages.