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The AI Insurance Group

Notes from inside the market.

What I'm watching, reading, and reacting to as the AI insurance market reshapes itself in real time.

April 20265 min read

What Sullivan & Cromwell Just Told Every Underwriter About AI Risk

The firm that advises OpenAI on safe AI deployment filed a brief riddled with AI hallucinations, despite written policies, training, and manual citation review. For carriers, that's not a punchline. It's the clearest signal yet about what AI exposure actually looks like inside the most sophisticated firms on Wall Street.

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April 20264 min read

AI Hallucinations: Why Lawyers and Doctors Need an Endorsement, Not a Hope

Over 1,300 documented AI hallucinations in court filings. Peer-reviewed studies show AI fabricates medical references up to 47% of the time. If your malpractice carrier is treating this as "covered professional error," read the fine print before your next renewal.

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September 20264 min read

Why Most Homeowners Don't Have an Umbrella Policy

Most people know umbrella insurance exists. Very few have ever been asked about it. Here is what it does, and the gap most people never check.

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September 20265 min read

Your House Costs More to Rebuild Than Your Policy Thinks

The dwelling limit on your declarations page was probably set years ago. Construction costs did not wait. Here is what to check.

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September 20264 min read

Your Home Insurance Is Hiding in Your Mortgage Payment

If your insurance is paid through escrow, you may not have looked at its price in years. Here is what has changed, and what to check.

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May 20265 min read

The SEC Already Started Hunting 'AI Washing.' Your D&O Policy Probably Doesn't Mention It.

The SEC just won its first AI washing enforcement case. Over 40% of S&P 500 companies mention AI in their annual reports. Most of their D&O policies don't address AI exposure at all. Aon's recent guidance maps the gap, and it's wider than most boards realize.

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May 20264 min read

Diligence Isn't a Defense: Why 'Using AI Carefully' Won't Save You

A NewsGuard study just found Claude, previously the most reliable AI on the market, repeating Russian and Iranian propaganda 15-20% of the time. The lesson isn't about Claude. It's about every AI tool your business uses, including the ones you trust.

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May 20264 min read

Five AI Cyber Threats Your Underwriter Is Already Pricing For

Great American Insurance Group's Cyber Risk Division just laid out, in plain English, the AI-driven attack categories reshaping how cyber policies are written. If your renewal feels different this year, this is why.

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April 20265 min read

We Built This in 90 Days. Here's Why That Matters.

On January 1, 2026, major carriers started attaching AI exclusions to standard commercial policies. Most businesses don't know. Most brokers aren't equipped to help. We built a platform to close that gap, before the industry catches up.

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