In the summer of 1645, the Oratorian Virgilio Spada (1596–1662) acquired a painting of a debate on astronomy by the Sienese artist Niccolò Tornioli (1598?–1651) and displayed it in the Palazzo Spada, the Roman residence of his older brother, Cardinal Bernardino Spada (1594–1661). Our discussion of The Astronomers questions some of the traditional identifications of its characters, although we cannot claim to have solved these figures’ identities and several remain a mystery. We do present new iconographic interpretations of particular scientific instruments, diagrams, and natural phenomena in the canvas. These novel readings occasionally remain conjectural in part because Tornioli represents these entities in a way that makes it clear that he did not fully comprehend them. The errors and obscurities in Tornioli’s painting lead us to two conclusions. First, that the erudite Virgilio Spada was unlikely to have been involved in the definition of the painting’s iconographies, as he would have objected to Tornioli’s crass mistakes and obscure imagery. Second, that these errors and indistinct details should be taken at face value, insofar as they accentuate the difficulties of astronomical observation. Beyond highlighting these challenges, we argue that the painting also visualizes techniques for countering them. Specifically, the canvas would have focused early modern observers’ attention on the edifying powers of civil conversations and communal observations with scientific instruments as well as images—including diagrams, celestial maps, and paintings.