Dionysios Stathakopoulos’ chapter is divided in two parts. In the first he presents the textual sources that have had a seminal influence on the establishment of a visual vocabulary of transgressions that appear in depictions of Hell in monumental painting. He focuses on the development of ideas of punishment in the afterlife, tracing their origins from the Old and the New Testament and apocryphal texts to late Byzantine theology, which were popular in shaping ideas on punishment. Since, however, they do not always assist our understanding of the iconography of Hell, as this also reflects the social preoccupations of the community that commissioned the cycles, Stathakopoulos, in the second part of his chapter, turns to Joseph Bryennios (born around 1350), who recorded a vivid depiction of his experiences during his appointment on Crete, in an attempt to look into the contemporary society that commissioned the Cretan Hell cycles that lie at the heart of this publication.