This dissertation examines the supernatural’s presence in late medieval exempla in Latin and vernacular traditions. It begins by presenting the challenges in defining what people understood as real in the late Middle Ages and what they believed constituted a violation of the natural course of events. Then, the discussion moves to a literary definition of the exemplum, whose existence as a proper genre is only sometimes accepted in the scholarship. The dissertation then studies the exemplum in vernacular sermons focusing on Giordano da Pisa and Bernardino da Siena, didactic texts, and hagiographies, including the Legenda Aurea. This overview shows how the supernatural functions differently according to a diverse array of preachers, who base its use on their mission and the ways they wanted to reach it. The core of the dissertation is a discussion of the supernatural as a literary and pedagogical device in late medieval anonymous miscellanies. By examining over twenty manuscripts in various libraries in Europe and the United States, this study explores how these miscellanies transmit hundreds of exempla that convey many values and reflect social habits and norms. Finally, the last part investigates the supernatural and the exemplum in their relationship with other literary genres, concentrating then on the novella and the Decameron. It shows the connection between the exemplary genre and secular literature, and how the supernatural in the exemplum is subverted in the novella and replaced with jokes, witticism, and more human substitutes. This dissertation demonstrates that, by using the supernatural, writers and compilers could personalize these texts and their lessons and increase their literary value; this shift changed the balance between teaching and entertainment, inevitably moving the focus from the former to the latter and giving voice to these authors.