Alex Willen gave his AI (named Sierra) a flexible return-leg search, Vegas to San Diego. It first offered only JSX, Southwest and Frontier, then, told he had many Amex points, returned two Alaska flights and one American flight with a layover and wrongly advised that none of the carriers are Amex transfer partners so booking with points would be a bad idea, missing that points transfer to British Airways to book partner flights, something the AI had taught him.
This one went wrong. See what happened before you try it.
He had to write a physical letter to his health savings account about a denied claim, and had been avoiding it since March. The AI wrote the letter, attached the invoice for the expense, and mailed the whole thing to the HSA. His only job was taking over for the $2.31 payment. Whether the claim was then paid is not stated in the comment.
This only partly worked. Worth knowing before you try it.
Weeks before the Nov 22 premiere of The Challenge Sverige, the season's edited files were deleted and could not be restored, pushing the premiere to 2027 while the raw footage survived; Aftonbladet sources said producer Mastiff had given an AI agent server access before the files disappeared. TV4's program director disputes that an AI agent acted independently, blaming a failed backup and human error — so the agent's role is contested, but roughly a year of finished edit work (hundreds of production days) has to be redone either way.
This one went wrong. See what happened before you try it.
He let an AI run his HighLevel affiliate site for two weeks. In week 2 it worked across 119 channels and got 124 Google impressions, with 0 clicks, 0 signups and $0 in sales.
This one went wrong. See what happened before you try it.
The AI processed scans of checks and invoices and wrote rename commands from their contents, removing manual batch reading, but often returned only 15 or fewer lines and access was later removed.
This only partly worked. Worth knowing before you try it.
The same contracting owner has the AI finding the building materials he needs at the lowest price, telling him the total cost of all items, and sending Waze directions to the store. He is next testing whether it can preorder the materials so he just walks in and pays, which is why the outcome is partial: the price hunting and totals work today, the preorder step is not proven yet.
This only partly worked. Worth knowing before you try it.
He has the AI dedupe and reorganize his NAS. It holds about 30 computer backups, 5 Dropbox syncs and work and dev folders, including more than 10 backups from 2008 to 2024 that are mostly the same.
This only partly worked. Worth knowing before you try it.
Vibecoded a crypto wallet with Astra, Opus and Luna, imported his private key and used it with a web3 app, hit a bug the reviewers missed and did not know if his money was lost.
This one went wrong. See what happened before you try it.
An engineer had just had the AI reapply local, uncommitted code changes. Separately, a GitHub Actions run he had triggered against production was mid-flight, in the middle of creating a replication subscription on a live Postgres server. He said undo the work it just started, meaning the local edits. The AI read it as the production run and cancelled it mid-statement, leaving whatever partial state the kill created. The local edits were not touched until he clarified.
This one went wrong. See what happened before you try it.