This thesis is a study of all aspects of writing and reading connected with Sir John Fastolf, a military captain and steward of the household of John Duke of Bedford, who returned to England from the later battles of the Hundred Years War in 1438. Using the circumstantial, palaeographical, and codicological evidence contained in the letters, documents, and literary texts associated with Fastolf, the thesis performs a survey of the men who wrote for Fastolf, their interactions with him and with each other, and their positions in what might be deemed a ‘readership community’. The thesis takes a detailed look at letter and document composition, delivery, and storage, then relates this administrative writing to the production and reception of texts in manuscript books. It argues that there was a close relationship between these two types of work, finding that the administrators of the Fastolf circle were also the scribes of literary texts. The thesis consistently reinforces the importance of oral communication within this circle, emphasising that though there is a substantial amount of surviving written material associated with this circle, the written word was not the sole form of communication within it. The first section of the thesis is an introduction to the circle of Sir John Fastolf,since it is necessary to comprehend this complex and multitudinous group before considering reading and writing within it. Chapter One gives biographical information about Fastolf and the associates who were most involved with writing and reading. It then reconsiders the highly-contended issue of Fastolf's relations with these men: was Fastolf a harsh master, or badly-served by his men? Chapter Two explains the choice of the word ‘circle’ to describe this group, and considers potential subdivisions within it according to responsibilities or linguistic descriptions. It emphasises the individuality within the master-servant relationship, as is indicated by the evidence that Fastolf’s servants maintained various levels of proximity and permanence of service. In the second section, Chapter Three is a detailed examination of the writing of letters and administrative documents. It opens with a discussion of the interplay between oral conversation and written correspondence. It then looks at the evidence for the way in which Fastolf’s letters (none of which were autograph) were composed, and argues that they were not dictated. It progresses to examine the practicalities of correspondence and administration: drafting, copying, letter delivery, and storage. Finally, there is a look at the watermarks of paper associated with Fastolf. This leads into Chapter Four, which is a study of interactions between the men who wrote for Fastolf. It shows that there was consistent co-operation between Fastolf’s scribes, and suggests that collaboration had an effect upon the linguistic features of their work. Finally, Chapter Five looks at Fastolf’s collection of literary manuscript books, and considers the evidence about who read literary texts, as indicated by circumstantial evidence, as well codicological evidence such as annotations within the books themselves. It provides case studies of the men who can be shown to have written these books, and a focused study of one of these books in particular, the hitherto under-studied manuscript, College of Arms, MS. Arundel 48. Finally, there is an overview of the formation of a sub-section of Fastolf’s readership community in the west country, especially in Bristol, Glastonbury and Wells, which was facilitated by Fastolf’s Bristol-born secretary William Worcester.