I have to admit that until I saw this headline, I had not been aware of this activity:
[Apr 24] Berkshire and Chubb Cleared to Drop AI Coverage
https://cybercorsairs.com/berkshire-and-chubb-cleared-to-drop-ai-coverage/
As it turns out, this is not a new development.
On October 6, 2025, The Financial Times of London had this headline (paywalled content):
Insurers balk at multibillion-dollar claims faced by OpenAI and Anthropic
The story was picked up by multiple sources. But then these kinds of articles began to appear:
[25 Nov 2025]
Major Insurers Retreat from AI Coverage as Multi-Billion Dollar Risk Concerns Mount
https://theoutpost.ai/news-story/major-insurers-retreat-from-ai-coverage-as-multibillion-dollar-claims-risk-mounts-21926/
[03 Dec 2025]
Insurers Could Pull Back From AI Coverage - What It Means for Businesses
https://www.fasken.com/en/knowledge/2025/12/insurers-could-pull-back-from-ai-coverage
“Behind this trend lies a deeper concern. AI models remain difficult to audit, unpredictable in their behavior, and often opaque even to their creators. When something goes wrong, the chain of responsibility can span developers, model providers, integrators, and end users, making liability hard to pinpoint.”
[26 Jan]
The headline is in the URL:
https://www.folio3.ai/ai-pulse/ai-giants-openai-anthropic-turn-investor-funds-cover-mounting-legal-costs
“OpenAI and Anthropic are exploring using investor funds to settle multibillion-dollar copyright lawsuits as traditional insurance falls short. OpenAI has secured only up to $300 million...”
You might recall hearing how both companies incurred substantial penalties in ongoing legal cases.
[Mar 7]
Insurers Draw Battle Lines on AI: New Policies Cover Hallucinations While Others Exclude AI
https://aiproductivity.ai/news/ai-liability-insurance-coverage-exclusions-2026/
“This is the clearest sign yet that AI deployment risk is being priced by the market, not just debated in policy papers. Insurance actuaries don’t care about hype cycles.”
[Apr 9] The title is in the URL:
https://www.cio.com/article/4159297/insurance-carriers-quietly-back-away-from-covering-ai-outputs-2.html
“Dozens of insurance carriers appear to be rethinking coverage for mistakes related to AI, including this quote, “Many insurance companies aren’t comfortable with covering AI outputs because they can’t track the reasoning path the AI took to come up with a result,...”
[Apr 13] Al Exclusions in Insurance Policies: Broad Language, Uncertain Impact
https://www.policyholderpulse.com/ai-exclusions-insurance-policies/
(quoted from, but reduced for brevity)
The Expanding Landscape of Al-Related Litigation
-Copyright and IP claims arising from the training of large language models onallegedly protected works
-Privacy and data-use claims challenging the scraping or use of user data for Al training
-Antitrust claims alleging misuse of proprietary data in Al development
-Discrimination and algorithmic bias claims alleging that Al systems produce discriminatory outcomes
-Al-related securities class actions, where plaintiffs allege misleading statements about Al capabilities or prospects
I picked these articles to show the timeline, but also as a sampling of the issues involved. All of these articles contain numerous other details.