Algorithmic Insurance

When AI systems make errors in high-stakes domains like medical diagnosis or autonomous vehicles, a single algorithmic flaw across varying operational contexts can generate highly heterogeneous losses that challenge traditional insurance assumptions. Algorithmic insurance constitutes a novel form of financial coverage for AI-induced damages, representing an emerging market that addresses algorithm-driven liability. However, insurers currently struggle to price these risks, while AI developers lack rigorous frameworks connecting system design with financial liability exposure. We analyze the connection between operational choices of binary classification performance to tail risk exposure. Using conditional value-at-risk (CVaR) to capture extreme losses, we prove that established approaches like maximizing accuracy can significantly increase worst-case losses compared to tail risk optimization, with penalties growing quadratically as thresholds deviate from optimal. We then propose a liability insurance contract structure that mandates risk-aware classification thresholds and characterize the conditions under which it creates value for AI providers. Our analysis extends to degrading model performance and human oversight scenarios. We validate our findings through a mammography case study, demonstrating that CVaR-optimal thresholds reduce tail risk up to 13-fold compared to accuracy maximization. This risk reduction enables insurance contracts to create 14-16% gains for well-calibrated firms, while poorly calibrated firms benefit up to 65% through risk transfer, mandatory recalibration, and regulatory capital relief. Unlike traditional insurance that merely transfers risk, algorithmic insurance can function as both a financial instrument and an operational governance mechanism, simultaneously enabling efficient risk transfer while improving AI safety.