The expansion of blockchain technology and the evolution of digital platforms have led to the emergence of new concepts in contractual relations, of which "smart contracts" are among the most significant. These contracts are designed as blockchain-based computer programs that execute the terms of the parties' agreement in the form of digital codes and enable the automatic performance of obligations without the need for traditional intermediaries. Such features have increased the speed, transparency, and efficiency of transactions. However, the introduction of this technology into the field of contract law has raised fundamental questions regarding the legal nature, validity, and enforcement of such contracts in various legal systems, particularly those based on classical traditions. The aim of this research is to elucidate the legal nature of smart contracts and analyze the challenges of their enforcement in the Iranian legal system. The research method is descriptive-analytical, and data have been collected through library studies and the examination of domestic and international legal sources. The findings indicate that, despite technical differences, smart contracts can be analyzed within the framework of general contract rules. The principle of party autonomy and Article 10 of the Civil Code provide the capacity to accept this type of contract, and the Electronic Commerce Law, by recognizing data messages and electronic signatures, has established a basis for the validity of digital transactions. However, challenges such as ascertaining the true intent of the parties, determining liability for technical errors, and the conflict between the immutability feature of blockchain and institutions such as rescission and mutual rescission persist. Accordingly, the formulation of supplementary regulations, the development of legal infrastructure, and the enhancement of specialized knowledge appear essential for the safe and effective utilization of this technology.