This article attempts to understand the outcomes when each party of an insurance contract simultaneously has superior information. I assume that policyholders have superior information about specific risks while insurers have superior information about general risks. I find that low-general-risk policyholders purchase insurance, while high-general-risk policyholders are self-insured. Among the low-general-risk policyholders, high-specific-risk policyholders purchase full insurance, while low-specific-risk policyholders purchase partial insurance. When insurers can strategically publicize their information, efficiency is improved because high-general-risk policyholders purchase actuarially fair insurance. The market segmentation is also found based on the general-risk type and the publicizing of information.