Monastic waqf landholding and its exploitation in the Ottoman Empire followed the trajectory of ottoman Hanafi jurisprudence and imperial legislation. From the first attempts to regulate Christian land waqfs through Mehmet the Conqueror’s jurisconsult Molla Khusrev to their successful legalization by the efforts of Suleyman the Magnificent’s şeyhülislam Ebu’s-su’ud, monastic land waqfs, they not only retained their economic role in their regions but managed to expand their influence beyond their immediate environs. This paper using primarily examples from the monastic communities of Mount Athos and exploring archival material in ottoman Turkish and early modern Greek, will discuss the legal culture of monastic communities and the methods they employed to defend and expand what they consider their God-sent burden, their landed endowed properties. Through court cases heard locally in the presence of the kadi, or the Imperial Divan and the Synod, we will attempt to unravel the variety of legal norms and tools used by the monks to defend “their” right against local aggressors, tax collectors and daily cultivators and their strategies, until the promulgation of the Ottoman Land Law of 1858. Moreover, through these court cases, we will follow the transformation of land use from the 17th to the 19th centuries.