Sarajevo was the capital of the sancak of Bosnia from its Ottoman conquest in 1463, until it was moved to Banja Luka in 1580. Unlike Istanbul, Damascus, and other Ottoman cities, Sarajevo did not exist as a city before it became an Ottoman provincial center. Free from the need to convert an existing city, in this case the Ottomans had the opportunity to create a city tailored to their imperial needs. The process of city-building started with Bosnia’s conquest in the 1460s and continued for centuries. According to an early-seventeenth-century survey, however, by as early as 1604 Sarajevo had 194 mosques, five schools, sixteen public baths, and fourteen inns. The establishment of all of these public institutions was funded by waqfs (charitable endowments). During the expansionist period of the Ottoman Empire in the fifteenth and sixteenth centuries, waqf was an important instrument for the Islamization of newly conquered territories, as the Ottomans often sought to transform and modify the character and topography of cities and towns as well as to visibly assert their imperial capabilities to the local population. In this paper I analyze the influence of the waqf on the urban development of Sarajevo, by performing a contextualized reading of fifteen waqfiyyas (endowment deeds) from fifteenth- and sixteenth-century Bosnia and comparing the information contained in these documents with other accounts of the development of Sarajevo, largely based on tapu tahrir registers. Based on this analysis, I argue that the institution of the waqf was instrumental to the development of the city of Sarajevo in three main ways: first, waqfs encouraged the actual growth of the city and strengthened its relations with its hinterland; second, they were integral to promoting the Islamic character of the city and that of the everyday life of its inhabitants; and finally, they played a pivotal role in making the city part of a larger network of Ottoman communities.