This article offers a new perspective on the anonymous Liber beati et laudabilis viri Gregorii. The oldest extant life of Pope Gregory the Great, the Liber was composed at the double monastery of Strænæshalch, conventionally known as Whitby, under Abbess Ælfflæd probably between ca. 704 and 714. A principal concern of my article is the function, within the Liber, of its report of Gregory's encounter with a group of Deiran Angles in Rome, and that story's relation to the emphasis throughout the Liber on orality: the transmission of knowledge miraculously from heaven and through earthly channels by means of speech and other sounds. The Liber survives in an early ninth-century redaction, part of St. Gallen, Stiftsbibliothek, Cod. 567 (pp. 75–110). After discussing some issues that pertain to the modern edition and translation made by Bertram Colgrave from this manuscript, I compare the legend of Gregory and the Deirans in the Liber with the version in Bede's Ecclesiastical History. I then review the larger hagiographical narrative in which the Whitby author frames this episode, and I examine the story and other distinctive thematic as well as stylistic aspects of the Liber in the light of the following circumstances: seventh- to eighth-century regional developments that affected Whitby; conditions of teaching at this monastery, a major early English educational center; the documented interest at Whitby under Ælfflæd, as under her predecessor Hild, in heaven-inspired or miraculous forms of oratory; and liturgy and commemoration of the dead. Of interest for analyzing all these topics, but especially the last two mentioned, is Whitby's status as a female-led institution.