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This paper delves into the long-debated tensions that critics have found in Edgar Allan Poe (1809-1849)’s writings, which have placed him as a liminal figure between the Enlightenment and Romanticism. In particular, I will maintain that these tensions are representative of the contradictions inherent in the modern project, which I will argue are present in Poe’s writings and which situate Poe’s texts as both a symptom of and a reaction to the pathologies of modernity. To this end, I will consider Max Horkheimer and Theodor W. Adorno’s Dialectic of Enlightenment (1944), arguing that the problems addressed in the volume were foreshadowed by Poe’s writings a century earlier. After a brief introduction, I will analyse the widely-discussed “The Purloined Letter” (1844) and the attitudes towards rationality that Poe presents in the story. I will then explore the lesser-known “The Colloquy of Monos and Una” (1841),2 where Poe anticipates some of the problems that Horkheimer and Adorno voiced, most notably the confusion between progress and technification.