Stipulations within contracts (Shurūṭ Ḍimn al-‘Aqd) constitute an essential legal mechanism through which contracting parties can regulate their mutual rights and obligations beyond the principal terms of an agreement. In legal systems influenced by Islamic law, particularly Iranian law, contractual stipulations occupy a central position due to their deep roots in Imami (Ja‘fari) jurisprudence. This comparative study examines the concept, legal foundations, and conditions of validity, classifications, and legal effects of stipulations within contracts in Iranian law and Imami jurisprudence, with the aim of identifying points of convergence and divergence between the two systems. In Imami jurisprudence, contractual stipulations are regarded as ancillary commitments attached to the main contract and derive their binding force from both jurisprudential principles and religious sources, most notably the rule that believers are bound by their conditions (al-mu’minūn ‘inda shurūṭihim). However, their validity is strictly limited by conformity with Sharia, rationality, feasibility, and consistency with the essence of the contract. Iranian civil law, while largely inspired by these jurisprudential principles, adopts a codified and systematic approach, particularly in articles 234 to 246 of the Iranian civil code, and further reinforces contractual autonomy through article 10, which recognizes the freedom of private agreements within legal boundaries. The findings of this study demonstrate a substantial degree of harmony between Iranian law and Imami jurisprudence, especially in the classification of stipulations into conditions of attribute, act, and result, as well as in the legal consequences of breach. Nevertheless, Iranian law introduces modern legal concepts such as public order, legal certainty, and explicit statutory remedies, which distinguish it from classical jurisprudential analysis. Overall, the study highlights how Iranian law has preserved the substantive foundations of Imami jurisprudence while adapting them to the requirements of a modern legal system.