AI Exclusions Are Spreading. Most Companies Don’t Know They’ve Lost Cover, Erin Kenneally Says.

Cyber Insurance News podcast with Erin Kenneally of DLTASKOP, showing a dark radar screen with a blind sector and the words AI is being written out of your insurance

Erin Kenneally returns to the CINI podcast a year after warning that AI could repeat cyber insurance’s ransomware mistakes. Insurers are writing AI out of policies faster than they write it in, she says. Her new company, DLTASKOP, aims to give underwriters the evidence to price it. Most companies haven’t bought AI insurance. Many have … Read more

Every Month This Year Has Brought More Attacks, Kroll’s Incident Chief Says. He Sees No Peak Yet.

Cyber Insurance News story on ransomware trends with Kroll's Max Henderson, showing a steep mountain trail in daylight that climbs into cloud with the summit hidden

Every month this year has brought more attacks than the last, says Kroll’s Max Henderson. Not even the arrest of a ShinyHunters leader slowed it. Encryption is no longer needed, he told Cyber Insurance News. AI has opened extortion to lone attackers. Max Henderson is Global Head of Digital Forensics and Incident Response at Kroll. … Read more

Most AI Agents Don’t Say Who They Are. The Business Usually Carries The Loss.

Cyber Insurance News report on AI agents showing a laptop filling in a checkout form by itself beside a coffee cup and a payment card

AI agents are logging in, signing up, and checking out for real customers. Arkose Labs found only 2.3% of legitimate agent sessions carried a verified signature. When someone misuses an agent, CEO Kevin Gosschalk says, the loss usually sits with the business. Personal AI agents moved from reading the web to transacting on it in … Read more

GPT-6 Astra Asked Permission. An Automated Reply Said Use Your Best “Judgement.”

Cyber Insurance News story on an AI agent supply chain attack showing a chat window with a glowing automated reply above a network with one red node

The model asked before it acted. The reply came from a script. “Please proceed to the next step using your best [judgement].” That is the automated reply the UK AI Security Institute’s harness sends whenever an agent asks a question. OpenAI’s GPT-6 Astra sometimes read it as a yes. What followed, in simulation, was unsanctioned … 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

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