Good paper on cybersecurity insurance: both the history and the promise for the future. From the conclusion:

Policy makers have long held high hopes for cyber insurance as a tool for improving security. Unfortunately, the available evidence so far should give policymakers pause. Cyber insurance appears to be a weak form of governance at present. Insurers writing cyber insurance focus more on organisational procedures than technical controls, rarely include basic security procedures in contracts, and offer discounts that only offer a marginal incentive to invest in security. However, the cost of external response services is covered, which suggests insurers believe ex-post responses to be more effective than ex-ante mitigation. (Alternatively, they can more easily translate the costs associated with ex-post responses into manageable claims.)

The private governance role of cyber insurance is limited by market dynamics. Competitive pressures drive a race-to-the-bottom in risk assessment standards and prevent insurers including security procedures in contracts. Policy interventions, such as minimum risk assessment standards, could solve this collective action problem. Policy-holders and brokers could also drive this change by looking to insurers who conduct rigorous assessments. Doing otherwise ensures adverse selection and moral hazard will increase costs for firms with responsible security postures. Moving toward standardised risk assessment via proposal forms or external scans supports the actuarial base in the long-term. But there is a danger policyholders will succumb to Goodhart’s law by internalising these metrics and optimising the metric rather than minimising risk. This is particularly likely given these assessments are constructed by private actors with their own incentives. Search-light effects may drive the scores towards being based on what can be measured, not what is important.