In 1786, several hundred subjects of Tipu Sultan (r. 1782–99), ruler of the kingdom of Mysore in southern India, travelled to the Ottoman Empire on a diplomatic mission. This essay revisits the embassy's travels, and travails, across Eurasia and the Indian Ocean by drawing attention to a rich cache of administrative documents. I suggest that this collection, hitherto unexamined, can illuminate some significant aspects of diplomatic conduct and procedure in Islamicate Eurasia, yet underexplored. The essay accordingly highlights such overlooked themes as the bureaucratic complexities that were involved in long-distance ambassadorial tours, the role ceremonials played in elite intercourse, and the myriad ways in which material culture mediated interstate exchanges. While its significance lies also in how it decentres a dominant scholarly focus on encounters between Europe and its others, scrutiny of this collection, I additionally argue, can enhance historical understanding of how reciprocal relations between Islamicate polities transformed due to growing European influence. As contemporary configurations of imperial power changed in both South Asia and the Middle East, the Mysore-Ottoman embassy hence at once reflected and anticipated the advent of European—and more specifically, British—hegemony in non-European diplomatic contexts.