At the University of Sydney’s Shakespeare course, students use ChatGPT and other AI platforms to analyze Shakespearean metaphors, comparing AI-derived insights with established sources like the OED and editorial commentaries. This approach fosters an understanding of Shakespeare’s language as a dynamic, context-emerging entity, akin to AI’s ever-expanding neural networks. The assessment aims to acquaint students with future knowledge tools, assess these tools’ capabilities, and enhance their agency as literary critics. This iterative, comparative, and reflective technique offers a model adaptable to various disciplines requiring nuanced knowledge source analysis.