This paper aims to explore how the legal mechanisms allow exploitative relationships under the guise of charity, using the processes by which waqf revenues were reported as a case study. According to the dominant vision within the field, medieval waqf was a legally enshrined system by which grantors could ensure the wellbeing of their communities and their souls through selfless acts of ongoing charity. In rural context especially, the waqf capitalized on a large network of local notables whose testimony was trusted by officials and whose word became therefore essential to the functioning of the waqf. Wealthy grantors created the waqf through a series of contracts typically stipulating the grantor’s bloodline as the primary beneficiary and upon the bloodline’s extinction establishing some charitable cause as the alternate beneficiary. Most studies have focused on the waqf’s effects on urban beneficiaries, overlooking how this wealth was accumulated. Historiographical sources depict generous patrons distributing wealth to various causes. Although some waqf property was urban, much of it in fact came from farmland in villages far away from the sites of wealth distribution. My research in documentary sources reveals the pre-history of this wealth, and how it made its way to its various beneficiaries through the trusted testimonies of locals.