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This article argues that, in the Series, Thomas Hoccleve not only appeals to the system of patronage, but attempts to revise it, creating a new template for literary sponsorship and engagement based on collaboration and mutual responsibility. The process of literary production Hoccleve outlines supports a reading of patronage that is not exclusively financially-based; rather, it is flexible, less hierarchical, and demands more from the patron than Hoccleve’s previous work—and indeed the work of most medieval authors—would suggest. In order to understand Hoccleve’s attempts to redefine his relationship to the system of literary sponsorship, however, we must be willing to take the structure of the Series seriously, following the signposts of creative collaboration Hoccleve weaves throughout the texts rather than their misleading, seemingly random nature. In addition to offering an alternate reading of Hoccleve’s work in the Series, this article suggests new ways of thinking about literary patronage in the Middle Ages more generally.