Underwritten
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
The 21% Problem
One in five enterprises cannot stop a runaway AI agent in real time. Why that control gap decides whether your agents are insurable.
Read the essay →Series · New to insurance? Start here
The First Claims
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.
Part 1 · Live
The First Claims, Part 1: What the Machine Said
The first AI liability claims are about what the machine said. A chatbot's false promise and a fabricated accusation show insurers where an old exposure now speaks in a new voice.
Part 2 · Live
The First Claims, Part 2: What the Machine Did
The first AI liability claims are also about what the machine did. Biased hiring algorithms and the fight over training data show where the biggest exposures are, and where the exclusions are moving fastest.
The Questions Before the Policy
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.
Part 1 · Scheduled
The Questions Before the Policy, Part 1: Why Underwriters Price the Company
Arrives August 28, 2026
Part 2 · Scheduled
The Questions Before the Policy, Part 2: The Underwriter's File
Arrives September 2, 2026
All essays
The 21% Problem
One in five enterprises cannot stop a runaway AI agent in real time. Why that control gap decides whether your agents are insurable.
The First Claims, Part 2: What the Machine Did
The first AI liability claims are also about what the machine did. Biased hiring algorithms and the fight over training data show where the biggest exposures are, and where the exclusions are moving fastest.
The First Claims, Part 1: What the Machine Said
The first AI liability claims are about what the machine said. A chatbot's false promise and a fabricated accusation show insurers where an old exposure now speaks in a new voice.
Who Insures the Machine
After the exclusions wrote AI out of ordinary policies, a real and fast-growing market formed to write it back in. Here is who now sells affirmative AI cover, and how that market is actually built.
The Price of Not Knowing
Insurance runs on loss history and large numbers, and AI offers almost none of it, which is why coverage is scarce, costly, and gated by what you can prove.
Coverage by Silence
For most of insurance history, silence in a policy tended to favor the policyholder. With AI, that silence is being written out of existence, and the burden of proof has shifted onto you.
Insuring the Machine Age
How the machinery of insurance met software, and why AI is the hardest risk it has ever been asked to price.
The Exclusion Machine
The insurance industry has met every new systemic risk the same way for a century, and in 2026 it turned that machine on AI.
Fire, Coffee, and Mathematics
How the Great Fire of London, a coffeehouse, and the first tables of the dead turned insurance from instinct into a discipline.
The Oldest Bargain
From a clause pressed into Babylonian clay to the arrival of AI coverage, how humans first learned to pool the risk no one can bear alone.