This article uses a descriptive-analytical method to conduct a comparative study of the structural and legal challenges in the two Islamic endowment institutions in Iran and trusts in the United States, and through pathological analysis, it sheds light on the weaknesses in the system for protecting and supervising endowment or trust assets. In Iran, although endowment is a long-standing institution with jurisprudential support, weaknesses in policymaking, inefficiency of supervisory institutions, and legal loopholes have made it vulnerable to crimes such as land grabbing, forgery, collusion, and hostile takeover. The most important challenges include the lack of specific criminal laws, the lack of criminalization of emerging behaviors, institutional interference, and the lack of transparent information infrastructure. On the other hand, the trust system in the United States, despite its effectiveness in circumventing "probit" and protecting privacy, has become a breeding ground for tax evasion and violation of beneficiary rights due to weak supervision and state diversity.Both systems suffer from three common weaknesses: lack of effective oversight, imbalance between authority and accountability, and lack of information and support infrastructure. Using a criminological and descriptive-analytical approach, the article emphasizes the need for multidimensional reforms in laws, supervisory structures, and management practices to ensure the security, transparency, and effectiveness of endowment and trust assets, and considers the relationship of these institutions to justice, public trust, and transparency as the key to their sustainability