Islamic Edowement (Waqf) Digitalization is an innovative breakthrough that can support waqf development. Currently, the waqf Collection, Management and Distribution (CMD) are eased by digital technology. However, there are unequal implementations among selected Organization of Islamic Cooperation (OIC’s) member countries that affected of the waqf progress itself. Several countries optimized this media as important tool to enhance the huge of cash waqf potential while others got stuck on classical obstacles such as regulation and human resources. Therefore, the study aims to identify and analyze several issues and find a proper solution regarding to current waqf’sdigital technology uses. This qualitative research use content analysis of several previous references that obtained from numerous reputable journals and other relevant sources. The results show that the basic philosophy of waqf digital technology is benefit, taysir, taghyiral ahkam, urf and maqashid sharia for great waqf improvement. Through this philosophy, several countries' studies have shown significant development of waqf. However, there are implementation differences between them since the budget is a matter. It takes large funds to be achieved. Government involvement is required to overcome the main obstacle. In addition, waqf human resource expertise is an important aspect to master. Therefore, recommendations of the study for future relevant strategies and frameworks are integrating Islamic endowment funds and government budgets to foster waqf operationalization as well as formulating an appropriate human capital collaboration.