For the realization of a data-driven society with a cyber-physical system (Society 5.0), the Japanese government is working on the social implementation of autonomous vehicles and robots with integrated artificial intelligence (AI). These new technologies have complicated mechanisms that operate with autonomous judgment, as in the typical example of autonomous vehicles. Furthermore, it is extremely difficult to prove the existence of liability for damages, which is the basis of liability insurance; in this respect, insurance contracts can be affected. In addition, with the development of information and communication technology (ICT), insurers can measure the dynamic risk of insured persons or objects of insurance in a state close to real time. Therefore, there is the possibility of “reverse selection,” which weakens the basis of the insurance system. Furthermore, the development of ICT makes it possible to replace a part of the body with elaborate prostheses, leading to the fusion of Things and Humans. Whether these prostheses should be protected by property insurance or life insurance is a new problem. Finally, when a data-driven society is established with a cyber-physical system, the threat of cyberattacks increases. Insurance covering the damage caused by cyberattacks should be divided into cyber risk insurance covered by normal insurance, war insurance, and terror insurance.