When Your AI Calls The Insurer’s AI, Who Owns The Mistake?

Cyber Insurance News conversation on consumer AI agents showing two smartphones exchanging voice waveforms above a policy document and pen

Consumer AI agents have started calling insurers to shop for coverage. In a conversation with Cyber Insurance News, Liberate co-founder and CEO Amrish Singh said a licensed human still signs. Who pays when the machine gets coverage wrong remains unsettled. The conversation began with a canceled flight. A major international airline canceled a flight I … Read more

The Machines Are Learning. Unfortunately, From Us.

We built AI on our own data, then got alarmed when it acted like us. An opinion on AI, agentic risk and who pays when the agent wanders off.

This essay originally appeared on “With Respect — Mostly,” Executive Editor Martin Hinton’s Substack, where he writes about a wide range of subjects, including cyber insurance and security. It has been adapted for Cyber Insurance News with additional reporting that ties it more directly to coverage we’ve done. Oh man. This was going to be … Read more

AI Risk Monitoring Failed. Claude Explained The Evidence Away.

Document lit on a dark surface casting a shadow that does not match its shape, illustrating AI risk monitoring failing when a model explained away the evidence

“If you are providing an AI-driven tool or service like Replit, would your network security liability policy cover customer lawsuits claiming that your AI agents conducted unauthorized access, data destruction, or transmission of malicious code?” Erin Kenneally asked that question in her September 29, 2025 guest essay for CINI. Nearly a year later, Anthropic has … Read more

AI Agents Went Outside Permissions Again. This Time The Targets Were Real People.

The UK AI Security Institute counted 19 unsanctioned actions across 122 test runs. It is the fourth such disclosure in three weeks. An AI agent opened a pull request on a stranger’s open-source project. The code carried a hidden malware dropper. A real person spotted it and warned the maintainer in public. So the agent … Read more

The AI Agents Got Out. The Bill Has No Name On It.

Somewhere in mid-July, two OpenAI models decided the sandbox was optional. Reporting indicates they exploited a previously unknown flaw, walked out onto the open internet, and broke into the production systems of Hugging Face, the AI model-hosting platform. OpenAI called it an “unprecedented cyber incident, involving state-of-the-art cyber capabilities.” Some might translate that as: our … Read more

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