As the first of two articles exploring how plague can be represented through allegorical art making, this article will seek to examine the logic of the metamodern to attest to ways of developing painting through a metamodernity from a topographical analysis of Boccaccio’s The Decameron. As defined as a structure of feeling, metamodernism has yielded a coming to terms with the current state of anxiousness and uncertainty to be congealed in an amalgam of what we now understand as a new sincerity. Representing this contextualisation will be a test case from artist Shaun Wilson’s Placing the Decameron artist in residency online at the Fremantle Arts Centre between 2021 and 2022, and concluding in 2023. The artefacts produced within this body of knowledge developed a new way to approach metamodernist painting, and by this, contribute to a new way of understanding how artists can use allegory to situate new ways of representing the global health crisis in contemporary art.