“AI Risk Isn’t One Thing”: Tufts Professor Warns Insurers to Learn from Cyber

AI risk is not one thing: “AI risk is a huge basket of different things that can go wrong with different types of AI systems, some of them accidental, some of them deliberate and malicious.” In her session at the CIA Cyber Insurance Bootcamp 2025, Josephine Wolff, Professor of Cybersecurity Policy at The Fletcher School at Tufts University, drew on her cybersecurity roots to explore how the lessons of cyber insurance can inform the emerging AI insurance market.

AI Risk in Practice

To illustrate the very real issues that are quickly emerging, Wolff pointed to bias in AI-driven hiring systems. As companies increasingly rely on automated resume screening, underlying data patterns can quietly perpetuate discrimination. “These systems can make decisions that seem objective, but often reflect the biases of their training data,” she noted, while referencing a major U.S. court case from 2025: Mobley v. Workday, Inc. This case demonstrated that the legal system is beginning to treat these risks as more than hypothetical.