This research, employing a descriptive and analytical approach based on data from library studies, aims to provide a portion of the legal literature necessary for the establishment and expansion of legal expenses insurance (insurance for litigation costs, legal representation, and legal advice). Based on the findings from a comparative study of the legal regimes of this type of insurance in the European Union, Switzerland, France, and Belgium, and considering the nature, purpose, and function of legal expenses insurance, this paper examines the obligations of both the policyholder and the insurer in these types of contracts, justifying and explaining them based on legal theories, principles, and rules. According to the research findings, in legal expenses insurance contracts, the obligations of each party constitute a balanced combination of various primary and secondary, financial and non-financial, and monetary and non-monetary obligations not found in other types of commercial insurance contracts. Consequently, we face the complexity of the legal regime for legal expenses insurance contracts, an issue that makes its establishment and promotion in Iran’s commercial insurance legal system contingent upon precise and appropriate regulation.