Scholarly work on modern South Asian pilgrimage to Mecca has focused mostly on the later periods of British colonialism, from the late nineteenth century to the first half of the twentieth century. This paper seeks to redress this gap in the literature by drawing attention to pilgrimage near the end of the eighteenth century and the beginning of the nineteenth century. It foregrounds the voices of pilgrims themselves, as opposed to imperial sources, to understand what kinds of political structures and entanglements surface in their accounts. It covers in particular the pilgrimages of two scholars from North India that were conducted in the context of Mughal decline and ascendant British power: Raf?‘ al-D?n Mor?db?d? (d.1809) in 1786 and Sayyid A?mad Shah?? (d.1831) in 1822. This paper analyzes shifts that occurred in the three and a half decades between their pilgrimages, in their articulation of imperial and legal politics from Delhi to Bombay and the Ottoman Hijaz, the material and cultural mechanisms of Muslim connectivity in the Indian Ocean, and the changing conceptions of the political geography of a Muslim world. Although their pilgrimages served different functions for them, this paper argues that their journeys and travel accounts served to cohere together a growing knowledge of the complex politics that pit Muslim states against a plethora of rising threats.