The present essay re-examines Dosso Dossi’s remarkable Jupiter Painting Butterflies (c. 1524; Cracow, Wawel Royal Castle), almost certainly made for Duke Alfonso I d’Este in Ferrara, proposing a novel reading of its enigmatic subject-matter as an allegory of painting. In a picture so clearly about artistic production, ironically, scholars have mostly lost sight of the visual milieu in which Dosso’s work once existed. Key questions regarding the picture’s initial location and display have received scant attention. This study seeks to recuperate that by reinserting the Jupiter into the rigorously planned ensemble of works ordered for Alfonso’s galleries. It begins by connecting the Wawel Jupiter’s allegorical imagery to burgeoning art theory in Italy from the fifteenth to sixteenth century, in particular the paragone, or rivalry between media in the visual arts. Fundamental to its pictorial structure is the humanist poetics of imitatio that spurred competition in Ferrara among resident artists and eruditi, but also between modern and classical models. What emerges is a clearer sense of the multifarious artworks with which the Dossi workshop sought to engage. These ranged from esteemed ancient prototypes and rare antiquities unattainable by Duke Alfonso, to contemporary art collections formed in Ferrara and at the neighboring Gonzaga court in Mantua. Ultimately, a new display location is proposed for Dosso’s Jupiter Painting Butterflies: the Camerini d’Alabastro of the Via Coperta. Installed here, nearby artworks Alfonso painstakingly assembled from Giovanni Bellini, Titian, Antonio Lombardo, and others, its imagery joined the dynamic dialogue with ancient and modern artistry across media. Finally, Dosso’s unusual depiction of a rainbow is linked for the first time to scientific inquiry in Ferrara, where its vivid meteorological imagery further celebrated painting’s superiority as a discursive and poetic medium.