An important new corpus of studies on communities throughout the Ottoman Empire has shed considerable light on the mechanics of collective representation and communal organisation. At the centre of these discussions is the well-known legal principle of the Hanefi school of Islamic jurisprudence whereby corporate entities are not recognised. Yet, as with so many instances from any conceivable context, legal principle and actual practice were not necessarily coinciding. Ottoman bureaucrats and legal scholars proved flexible and pragmatic enough to work round this conundrum, and the institutional evolution of structures of representation largely took place along the grey zone that lies between formally recognised and actually functioning modes of communal organisation that may transgress legal principle either in letter or spirit. This paper contributes to this discussion by examining the projection of institutional identity in eighteenth-century Ottoman Cyprus. This entailed a great deal of experimentation, the stretching of the meanings of titles, and arbitrary declarations. Through an examination of the usage of terms like kefil (guarantor) and reaya vekili (representative of the people) in Ottoman bureaucratic parlance, as well as the image of leadership projected by claimants of these titles, it is possible to delineate certain ‘official’ semantic boundaries, the flexibility of which allowed the claimants of such titles to draw legitimacy, power and authority as representatives of both the Ottoman state and local communities, by virtue of an institutional position. The creation and manipulation of such ambiguities (both by provincial and imperial actors) were fairly common in the administrative and institutional history of Ottoman Cyprus. In an attempt to elucidate these issues, this paper examines imperial orders, legal, fiscal or administrative documents, probate records, and Greek and Ottoman chronicles.