The option of stipulation (Khiyar al-Shart) is one of the important institutions of contract law through which the parties may reserve the right to terminate a contract within a specified period for one of the parties, both parties, or a third party. Despite being founded on the principle of party autonomy and Articles 399 and 456 of the Iranian Civil Code, the scope of this institution is not absolute in all legal relationships and must be assessed in light of the nature of the contract, mandatory legal rules, and public policy. Although marriage in Iranian law is based on mutual consent, it is a non-commercial institution founded upon familial and social interests, and Article 1120 of the Civil Code exclusively determines the grounds for its dissolution. Therefore, extending the option of stipulation to marriage is inconsistent with the structure of family law. Likewise, due to the unilateral and formal nature of divorce, the option of stipulation cannot be properly applied to it, and even revocation in revocable divorce does not constitute a contractual option in its legal nature. This study adopts a descriptive-analytical method based on library research and examines the issue through Islamic jurisprudential sources, statutory laws, and legal doctrine. The findings indicate that the direct application of the option of stipulation in marriage and divorce is not legally acceptable. Nevertheless, the Iranian legal system, through alternative mechanisms such as conditions of act, conditions of result, and power of attorney in divorce, provides a framework for the limited realization of the parties’ autonomy within the boundaries of the law.