Traditional reinsurance can transfer all the component of insurer's underlying risk including underwriting risk and timing risk. Since 1960s, financial reinsurance, which can transfer the timing risk and other financial risk arising from investment, currency exchange and interest, has been developed to obtain more capacity and smooth fluctuation of insurer's risk in the Lloyd's market. Regulators have struggled to develop the regulatory regime and as a result end up considering individual transactions one by one as necessary, by looking either at the substantial economic of the products, or at its form. Securitisation of insurance risk provides additional capacity for the insurance and reinsurance market by tapping the capital markets through insurance-linked securities. In general, a special purpose vehicle is created not only to provide reinsurance coverage for the ceding insurers but also to issue insurance-linked securities to the investors. The ultimate return can be based on the actual loss of the ceding insurer, or the performance of the relating index, or the occurrence or nonoccurrence of the specific event, or the physical parameters of the natural hazard. Finite risk reinsurance (financial reinsurance) and insurance securitisation are based on the reinsurance contract. As the main purpose of this article is to discuss the regulation of reinsurance and other relevant issues, it will focus on those transactions, which are formed as reinsurance contracts, particularly in financial reinsurance and securitisation of risk. With regard to finite risk reinsurance, the types of the instruments will be introduced and described as well as their characteristics. It is followed by the discussion of relevant regulatory issues arising from such reinsurance contracts. Several leading regulatory models then will be analyzed. Learning from these regulatory models, the suggestions based on a comparative analysis on these developed models will be provided. The second part of this article will discuss the regulatory issues relating to securitisation of insurance risk. First, the general structure of securitisation of risk will be identified. The subsection follow with an explanation of the motivations for insurance-linked securities taken into account with the policyholders, investors and insurers, focusing on characteristics which facilitate and hinder transactions. Furthermore, the regulatory issues relating to securitisation of risk will be discussed. This will be followed by the analysis of some developed regulatory models and conclusion.