AI Liability Insurance Buyer's Guide

All Essays · 13 Published

Underwritten

Essays on insurance, risk, and the arrival of AI liability coverage. Long-form history and analysis from the team behind the buyer's guide, each piece a doorway into the data.

Newest essay

· September 16, 2026
Essay

Guarantee or Indemnity

A performance guarantee pays when your AI fails to work. A liability policy pays when your AI harms someone else. Buyers lump the two together and end up holding the wrong one.

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Also in brief · the short version →

Series · New to insurance? Start here

The History of Insurance

01The Oldest BargainGenesis of insurance: pooling risk.July 22, 2026 →Also in brief · the 4-minute version →02Fire, Coffee, and MathematicsInception: from gamble to a discipline.July 23, 2026 →Also in brief · the 4-minute version →03Insuring the Machine AgePerigon: Insurance meets software.July 24, 2026 →Also in brief · the 4-minute version →Start with Part 1 →

The First Claims · 2 of 2 parts published

A two-part reading of the earliest AI liability claims, split by how the machine caused the harm: what it said, and what it did.

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The Questions Before the Policy · 2 of 2 parts published

A two-part guide to becoming insurable when there is no loss table: why underwriters price the company, and the nine-document file that makes you insurable.

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Standalone essays

Essays that stand on their own, outside any series.

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