The individual authorial voice of the late-medieval gentry letter-writer as heard in the context of private, familial or public land disputes is the focus of this thesis. It uses as its main sources two fifteenth-century letter collections which arise out of legal challenges: the Armburgh Roll and the letters of John Shillingford, a mayor of Exeter. The Armburgh Roll, c.1417-c.1453, focuses on a disputed inheritance claim and the affairs of the claimants Joan Armburgh and her husband Robert. The Shillingford letters detail a public dispute between the city of Exeter and the ecclesiastical authorities in the 1440s. The aim of this thesis is to further the understanding of the social and cultural attitudes of the fifteenth-century gentry through the analysis of the language and composition of their personal writings as well as to advance the historiographical appreciation of those gentry letters where they were written within the framework of conflict. It is both the deployment of a literary line of enquiry and a comparative study of the language, content and context of the letters that comprises the main strands of the study. It shows how by ‘reading between the lines’ and examining the individuality of the texts it is possible to reveal the thought processes that sit behind the individual writers’ words and therefore to gain a greater insight into the literate gentry strata. It demonstrates the importance of examining the letters with the emphasis on the politics of the writing which in turn reveals the emotional engagement that the individual gentry writer had with his or her own writing. Primarily, the thesis argues that by appraising the personal writings of the gentry with the emphasis on the creation of the texts against an appreciation of the complex ideological beliefs and concepts of the late-medieval period we can develop our understanding of gentry close personal relationships which in turn enables us to add to our knowledge of that important land-owning class and its evolving social hierarchy.