The first Ottoman description of Sofia, produced on the eve of the conquest in the 1380s, presented a rich city abundant in running water which, besides its value for a thriving local economy, produced a healthy and vigorous population. Later on, as a provincial capital, Sofia boasted of some of the most representative works of Ottoman architecture in the Balkans. The sixteenth century, the heyday in the construction of Ottoman Sofia, began with the construction of Yahya Paşa’s water supply system which survived into the post-Ottoman period and was inherited by the Bulgarian municipal authorities. In spite of this record of intense building activity, the image dominating both scholarly and popular literature on Sofia’s Ottoman past is that of an ‘Oriental village’ defined by its muddy crooked streets and frozen in its medieval timelessness. In treatments of Ottoman Sofia Bulgarian authors have gone so far as to produce a discourse that completely deprives the city of its urban status and the Ottomans of the ability to conceive of any ideas of urban space and a functioning public works system. This paper problematizes both the local, Bulgarian interpretation of the nature of the Ottoman city, and the Western perspective toward the Ottoman Balkans as an irrelevant addition to the study of Islamic and Ottoman urbanism. I approach the subject by using Ottoman sources demonstrating the perspectives of local actors and central authorities. The sources originate from kadı court records, vakıf administration, as well as various local and imperial administrative and political bodies. Most importantly, there is evidence of a communal spirit and a sense of collective identity in cases when early modern Sofia’s residents discussed issues concerning water supply with both local and state authorities and demanded the proper functioning of a public good. No less relevant are nineteenth-century sources demonstrating the efforts taken towards the maintenance of the water supply system. Complementing the Ottoman sources with archaeological evidence and documentation produced after 1878, the paper brings forward the existence of a rich urban culture and an identity molded by Ottoman urban practices some of which were even transferred into the post-Ottoman period. Thus, besides posing a challenge to local stereotypes and (mis)interpretations of Ottoman realities, the paper aims at emphasizing the importance of the Balkans for the study of Ottoman and Islamic urbanism.