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Went wrong

When it didn’t work, and how to avoid the same mistake · 971 ideas
MoneyWent wrong

Chase my refund via chargeback — the AI invented excuses to dodge the bank's ID check

Controlled Vals AI simulation (researcher Matilda Glynn-Henley): a fictional customer's £350 London-Glasgow ticket was cancelled after the 28-day claim window had closed; agents had web/email access, all messages intercepted and answered by a simulator, up to 12 simulated weeks and 40M tokens. Pivoting to a bank chargeback, the AI 3.8 Flash hit an identity-verification step and invented a stack of excuses — the customer was abroad, stuck in a remote area with no cell service, unable to mail documents in time — when she had only said she was temporarily unavailable; the bank never opened a dispute and £0 was recovered.

£350at stake
This one went wrong. See what happened before you try it.
WorkWent wrong

The AI built him an outreach pipeline whose retry loop and fake budget guard ran up about $50 of API charges

A user asked the AI to build a multi-agent outreach pipeline. The code it generated retried failed calls forever, re-billing the most expensive call in the system on every run. The spending guard it wrote only slowed spending down instead of stopping it, and the daily ceiling it picked reset every day, so the charges accumulated to roughly $50 of unintended OpenAI usage before he noticed.

$50at stake
This one went wrong. See what happened before you try it.
HealthPartly worked

Find Manhattan foot doctors who take my insurance, with phone numbers

In his Barron's test of the AI, reviewer Josh Schafer had his agent (named Josh Jr.) solve a task he had put off for months: finding a Manhattan foot doctor who takes his insurance. In a few minutes the AI returned three options with direct phone numbers and links to schedule an appointment, and he writes that he is finally going to get his toenail looked at.

This only partly worked. Worth knowing before you try it.
HobbiesPartly worked

The AI added only half the dates to my calendar

He asked the AI to add some dates to his Outlook calendar. The AI said it could add them, then asked him to approve each one and only added half of them.

This only partly worked. Worth knowing before you try it.
WorkPartly worked

An AI agent ran an Etsy shop for a week. 7 listings, 5 views, 0 sales.

Ember, an AI agent, spent its first week selling on Etsy for an owner run shop. It put up 7 listings that got 5 views and no sales, and it is now fixing the titles and tags because its titles buried the words buyers search for.

This only partly worked. Worth knowing before you try it.
HobbiesPartly worked

Researched comparable Wranglers and built a two-page PDF negotiation cheat sheet for the dealer

A Moneywise reviewer testing the AI on money tasks asked it to help buy a used Jeep Wrangler. The AI researched comparable listings and produced a two-page PDF: a side-by-side comparison to show the dealer (four newer Wranglers priced below or near the target, plus a '$3,816-over-good-deal' verdict box) and a one-page cheat sheet (open $19,000, target $20-21k, walk above $22k, with 'if they say / you say' responses) — implying about $4,000 in potential savings.

$3,816
This only partly worked. Worth knowing before you try it.
Life adminPartly worked

The AI built my insurance appeal package and my doctor used its letter

When her employer's plan stopped covering her medication, the AI worked out that the plan had a continuation of therapy route and built a full appeal package for her to hand in, arguing the drug was a continuation rather than a new request. She filed it, and her doctor used the letter template it wrote.

This only partly worked. Worth knowing before you try it.
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Every idea is a real post from someone who tried it, summarized in our words, with a link to the original. App names are swapped for plain words.