The principles of Michael Baxandall’s “The Period Eye” are complex enough to teach undergraduates in the introductory course in respect to active viewing of Medieval and Early Modern art. In an interactive in-class simulation, my students gain both a broad and individualized understanding of the seventeenth-century Dutch art market viewed with the corrective lens that digital technology provides them. In the session before the simulation, each student is given an identity card noting a specific individual artist, dealer, patron, or other individual who they will embody during the exercise. In addition to their name, the student is provided character’s occupation, budget, personal and professional connections, religious affiliation, and individual tastes. Students are encouraged to research their assigned identity online prior to the simulation, and those who take advantage of this discovered information that further propels them through the exercise. Some students are tasked with commissioning specific works or making a particular social connection but need to figure out which other individuals to seek out to accomplish these goals.