This chapter focuses on the non-life insurance industry, with an emphasis on corporate insurance. It begins by providing a theoretical overview of the importance of corporate insurance as an enterprise-wide decision-making process. The chapter then presents the findings of an original survey conducted with risk managers responsible for corporate insurance purchasing/management, discussing the challenges and future prospects of corporate insurance in Japan. The survey results reveal that, even in Japan’s leading companies, risk management departments are not fully integrated into the enterprise-wide financial decision-making process aimed at maximizing corporate value. As the non-life insurance industry’s main postwar market, automobile insurance, becomes increasingly saturated, the corporate insurance sector may attract more attention in the future. The chapter emphasizes the need for developing organizations and personnel capable of understanding the importance of purchasing corporate insurance as an important part of financial decision-making, much like in the broader corporate sector. Comment for this chapter identifies two reasons why Japanese firms have struggled to adopt enterprise risk management (ERM) systems: internal and external challenges. Regarding external issues, it highlights shareholders’ perceptions of risk financing and argues that the low survey response rate in this chapter may reflect these concerns.