Breach of contractual obligations is one of the most significant challenges in the Iranian legal system, with extensive economic, social, and legal consequences. This study employs an analytical-comparative approach to examine breaches in Iranian law, judicial practice, and Shia Islamic jurisprudence, while comparing them with the legal systems of France, England, and the United States. Findings indicate that weak contract drafting, ambiguous terms, and insufficient awareness of the parties are primary causes of breaches. Iranian law and Shia jurisprudence emphasize the principles of pacta sunt servanda (fulfillment of obligations) and compensation for damages. However, Shia jurisprudence provides stronger civil and penal enforcement in cases of bad faith or intentional breach. Comparative analysis shows that specific performance, fundamental breach, and claims for diverse damages are effective approaches to reduce breaches. Judicial precedents reveal that enforcement and compensation are the main remedies, while alternative dispute resolution methods, such as arbitration, remain underutilized. Legal education and the promotion of good faith and fairness serve as effective preventive tools. The study recommends legislative reform, strengthening of enforcement mechanisms, promotion of arbitration, and integration of jurisprudential principles to enhance legal certainty, social trust, and judicial efficiency.