This essay discovers new contexts for a manuscript of Dives and Pauper copied, according to its colophon, in Lisbon in 1465. I connect the making of this Middle English book (now New Haven, Beinecke Rare Book & Manuscript Library, MS 228) to the Lisbon confraternity of Santa Catarina, which counted six English merchants among its members. First, I consider the book as an artifact of the culture of lay religious reading and book charity in these merchants’ ports of origin, London and Bristol. I then contextualize the making of the book in the resident English community of fifteenth-century Lisbon. Membership in Santa Catarina brought these merchants into contact with the bureaucrats and chroniclers of new Portuguese ventures of settlement and enslavement along the African coast. These contexts open up new questions about how this work of Middle English instruction in Christian charity and obedience served those of its late medieval readers visiting Lisbon, a place periodized as the launching point of transatlantic modernity.