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In Part I, Treatise 22 of his Logica magna, Paul of Venice (c. 1369–1429) considers an interesting epistemic puzzle, whether something known by something is uncertain to him or not known to him. The analysis of this puzzle involves logic, epistemology, and obligational reasoning, making it a fascinating puzzle for scholars of the history of logic to try to solve. In this chapter, we look at one portion of this puzzle and attempt to understand the pattern of reasoning involved in it through the use of modern symbolic logic and the historical analysis of Paul’s texts and contexts. In doing so, we are indebted to the work of Mikko Yrjönsuuri, who has throughout his long and illustrious career in the history of logic combined both methods to not only illuminate medieval logic but make it accessible to modern logicians.