Today, translation is frequently delegated to machines. But despite impressive technological advances, literary texts quickly demonstrate the limits of artificial intelligence. Why do sophisticated machines struggle with literary translation? We will address this question by engaging perspectives articulated by a range of influential thinkers – from Luther’s reflections on translating the Bible, to Goethe and Schleiermacher’s thoughts on translation as an interpretive act, to twentieth-century responses developed by Nietzsche, Benjamin and Szondi. Over the course of the semester, students will create a structured portfolio of their own translations with critical reflections that will connect their experiences as translators to issues broached in the theoretical texts. Equipped with a nuanced appreciation of translation as an art, we will turn our attention to machine translation and critically assess the affordances and limitations of translation engines to generate satisfactory output in response to a variety of literary and expository genre. Our discoveries will provide us with a deeper understanding of specific characteristics of literary discourse. Oral fluency in a foreign language is not required, but the willingness and comfort to engage with a language other than English using dictionaries and other tools is required.