Contract interpretation, as one of the most fundamental and at the same time most complex issues in contract law, has always been of interest to legal scholars for a long time. The ultimate goal of contract interpretation is to discover the true will of the parties and achieve contractual justice; however, this process has faced numerous challenges and obstacles that can lead to incorrect interpretations, contradictory decisions, and ultimately disrupt the security of contractual relations. The present study examines and analyses the challenges and obstacles to contract interpretation in Iranian law with an analytical-descriptive approach. The findings of the study indicate that the challenges of contract interpretation in Iranian law can be classified into four main axes: ambiguity and incompleteness of contract words and lack of sufficient evidence; illogical results resulting from contract interpretation, including the problem of predicting contract breach, efficient breach, apparent representative, and the puzzle of obtaining illogical results; the impact of new technologies, especially block chain and smart contracts, on traditional methods of contract interpretation and enforcement; specific challenges of interpreting international contracts and conflict of laws. The results of this study show that despite the existence of general rules in the civil law, the Iranian legal system faces legal and procedural gaps in many cases and needs to amend and supplement the existing rules by taking inspiration from the interpretative approaches of comparative law and using legal analysis. The present study suggests that drafting accurate and comprehensive contracts, utilizing the services of expert legal consultants, developing coherent judicial procedures, and creating appropriate legal frameworks for new technologies are among the most important solutions to overcome the challenges in the process of interpreting contracts in Iranian law.