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Sir Nicholas O’Conor served as Britain’s ambassador extraordinary and plenipotentiary in Istanbul at a momentous time in the long history of Britain’s relations with the Ottoman empire. Throughout much of the eighteenth and nineteenth centuries, this relationship had produced one of the most important strategic alignments of the modern world, with implications for European and Asian security and for the maintenance of Ottoman territorial integrity. During the final decades of the nineteenth century, this bond came under severe pressure and in a number of ways the long-term decline of the relationship continued unabated until the outbreak of the First World War. The trend of disengagement was not uniform, however, and can be qualified in important ways by analysing in detail selected aspects of the relationship during O’Conor’s eventful residence. Certainly, relations between the two governments were often fraught in this period. The framework of the relationship, essentially the diplomatic engagement in Istanbul and London, was chronically flawed, not least by the creation of a negative Ottoman stereotype in Britain. The Ottomans were largely sidelined by the emerging system of international alliances and were frustrated by British encroachments into their imperial space. The existence of other pressures, such as the apparent threat posed to British interests by the Ottoman caliphate, did little to alleviate the tension. Despite this strained atmosphere, however, the relationship showed signs of fluidity and some notable overlaps in interests. With regard to the increasingly relevant Young Turk opposition, for example, the British government was more a staunch ally of Abdülhamid II (1942-1918 / r. 1876-1909) than, as might be expected, a beacon to reformists. Indeed, a central contention of this thesis is that while undoubtedly beset by difficulties, Britain’s relationship with the Ottoman empire shortly before the shock of the First World War was still salvageable.