This dissertation, Alchemical Fraud in the Middle Ages and Its Reception in Twenty-First Century Videogames, examines medieval criticisms of alchemy as they appear in Middle English and Scots poetry from the thirteenth to the fifteenth centuries to highlight the importance of alchemical hermeneutics and literary alchemy as medieval forms of interpretation. The alchemical hermeneutics validate and seek to understand how medieval and early modern alchemists read alchemy into nearly everything they encountered, even when no alchemy was intended to appear in the text. Literary alchemy provides a useful and important framework for classifying and understanding medieval alchemical references and metaphors, especially from writers whose texts were not meant to convey alchemical knowledge. The earliest text of this dissertation, Dame Sirith, contains no alchemy, but it contains many of the most important features which an alchemist would recognize. Criticisms of the trickster have much in common with contemporary criticisms of alchemists. Alchemists, tricksters, conmen, and con-artists are synonymous when their tricks deal in illusion, power over matter, and transformation. Even in Dame Sirith, there is literary alchemy, and finding it through alchemical hermeneutics allows for a greater understanding of women’s power, agency, coercion, and economic motivations during the rise of the merchant class in the medieval period. The other medieval texts all denounce alchemy in some form in their writings, even as they use alchemical references to strengthen their poetry. The final text is a videogame, Pentiment, which demonstrates a close association between alchemy and suspicion in its setting that straddles the late medieval and early modern periods. All together, these texts display the importance for alchemical metaphor and the presence of literary alchemy, even in texts not traditionally thought to have it.