Making AI mistakes coverable
When the most any AI can do is capped and every action is recorded, AI trading becomes something an insurer could cover.
This page describes a plan. reTrade does not insure or guarantee anything today, and we haven’t found an insurer that covers AI trading in people’s accounts.
Why insurance matters
Ordinary people trust the word “insured.” And insurers can push adoption faster than any sales team: when they make a safety step a condition of coverage, everyone adopts it.
What exactly would be insured
Nobody insures normal investing losses. What can be insured is the AI doing something you didn’t authorize. When a human adviser does that, it’s called a trade error, and advisers’ professional insurance already pays to fix it.
Schedule of cover
Planned. Plans depend on legal review and broker approvals.| What goes wrong | Example | What gets paid |
|---|---|---|
| Wrong trade | Wrong stock, wrong size, wrong direction, wrong account, the same order sent twice | The cost to undo it: the price difference plus fees |
| Rule broken | NVDA pushed to 22% when your rule says 15%, and then it falls | The loss on the part above your limit, compared with an order that followed your rules |
| Runaway AI | A loop that sends order after order | The cost to unwind everything it sent |
| Hijacked AI | Someone tricks or takes over your AI and it places orders you didn’t authorize | The loss from those orders |
| Tax mistake | One AI’s buy-back cancels another AI’s tax loss | The lost tax benefit (coverage of penalties varies) |
Not coveredA trade that followed your rules and simply lost money. That is normal investment risk.
Why today’s cover doesn’t fit
Brokers
They reimburse you when a hacker breaks into your account. But an AI you connected yourself counts as authorized, and Robinhood and Public say you carry all the risk for its trades.510
Cyber insurers
Their policies are written around “unauthorized access.” An authorized AI behaving badly doesn’t fit, and insurance writers are pointing out this exact gap in 2026.14
AI insurers
Armilla (in Toronto) and AIUC insure AI in general, like chatbots giving wrong answers. We found no product covering AI trading in people’s accounts.15
AI trading mistakes fall between policies.
How an insurer would enforce it
Insurers don’t watch every trade. They set conditions and only pay when the conditions were met.
No record, no coverage
Only orders with a reTrade record would be covered, giving every AI app and broker a reason to send every order through reTrade.
The price comes from your rules
The insurer would read your rules and one number we calculate, the blast radius: the most any AI can change in your account today without you. Tighter rules would mean a cheaper price.
Proof as it happens
The records would work like the driving-data box some car insurers use: continuous evidence instead of a yearly questionnaire.
Fast, fair claims
The record shows what was asked, what the rules said, what was sent and what filled, so an insurer could work out what the loss would have been if the AI had followed your rules.
Lying cancels the cover
In 2022 an insurer went to court to cancel a company’s cyber policy after the company misstated its login security.16
This has happened before
What we’d guarantee
reTrade blocks rule-breaking orders, so what’s left to insure is mostly reTrade’s own mistakes. That means we could make a simple promise, backed by an insurer:
If an order we approved breaks your rules, we pay.
Planned. Plans depend on legal review and broker approvals.Online shopping has a model for this: Signifyd and Riskified approve orders and pay the store back if an order they approved turns out to be fraud.
The honest part
If reTrade works well, claims should be rare, so premiums stay small. Insurance matters here for trust and adoption more than as a source of revenue. We would partner with an insurer, not become one, because selling insurance needs licences.