By the end of the sixteenth century, more and more men and women from the lands of Rum (Anatolia and the Balkans) were able to perform the hajj. This was in large part due to Ottoman efforts toward improving the infrastructure of the pilgrimage road via Damascus, efforts which had intensified following the incorporation of the Mamluk lands, including the Hejaz, into the Empire in 1516-17. As existing scholarship has shown, the Ottoman administration tried to solve recurring challenges such as water shortages, unscrupulous camelmen, and desert bandits by constructing fortresses on hajj routes and installing water sources within them, giving subsidies to potentially hostile bedouin tribes, and enacting policy designed to improve the quality and supply of camels. The focus of this paper, however, is an alternative set of actors: those who recognised the limitations of hajj infrastructure and sought to resolve this through the authorship of guides to the ritual (menasik) and the journey (menazil, ‘way-stations’) of the hajj. Composed in Ottoman Turkish by a variety of Rumi ulama, Sufis, preachers, and bureaucrats (‘hajj writers’), the guides offer a vital insight into the practice of hajj in the early modern Ottoman Empire, beginning especially in the late sixteenth century. Perhaps seeing the potential offered by the hajj to strengthen Sunni identity, hajj writers in the Empire encouraged their male and female coreligionists to avail themselves of this newly developed infrastructure, insisting that all obstacles could be overcome through their textual instruction. Some writers took care to provide medicinal remedies for the most common ailments accessible by all pilgrims, from the wealthy to the poor. Others asked pilgrims to take individual responsibility in ensuring that the hajj continued to be practiced safely and securely, for example by taking an active role in defending against bedouin attacks, thereby allowing for the continuing fulfilment of an important confessional obligation. They emphasised that it was not enough for pilgrims to simply rely on state measures, and that even in the absence of security, which hajj officials could not always guarantee, pilgrims were still obliged to undertake the hajj. At the same time, hajj writers could also place pressure on hajj officials by pointing out administrative failings or areas where infrastructure and organisation could be improved. Taking a more bottom-up approach, the paper shines a light on an important yet frequently overlooked dimension of pre-modern hajj practice.