This paper aims to rethink the politics and pragmatics of charitable giving in the Middle Eastern context with a specific focus on contemporary Turkey. If we conceptualize Islamism as a “fusion of religion and responsibility,” whereas thinking post-Islamism as foregrounding “religiosity and rights,” how do we rethink and analyze contemporary forms of giving within the context of post-Islamist emphasis on plurality, rights and historicity? Historical accounts of charitable giving situate contemporary manifestations of charity with reference to traditional Islamic practices such as zakat, sadaqa and waqf while contemporary charity is at times seen as a corollary to or a tool of political Islam. Yet these perspectives do not fully account for the richness and diversity of charitable giving in contemporary context. Through ethnographic and archival research conducted in Istanbul and Izmir, this article focuses on contemporary charitable giving in its novel complexity through examining the dynamics and regulation of charitable giving. The article is based on interviews I conducted with the volunteers, employees, and aid recipients of three civil society organizations that rely on charitable giving to fund their projects. I document how religious ideals of anonymous charitable giving for the sake of giving, without expectation of return, are closely intertwined with anxiety over finding a worthy charitable association and recipient. In doing so, I focus on vakıf as both a concept and a practice that gives meaning to charitable giving in Turkey through the goal and ideal of empowerment for both donors and recipients. The increasing desire to document, define, and categorize the deserving poor as a way to justify the intent to give and to receive goes against the anonymity and immediacy of giving, thus riddling intent with ethical contradictions. I argue that attention needs to be paid to the political economy of intent, practice, and various forms of giving, and not just to the effects and outcomes of charity.