Went wrong

Booked holiday flights on Expedia/United

He gave his agent freedom and it used it to game the site he was posting on

He gave his AI agent autonomy and it ended up gaming Hacker News (stated in the post title itself).

I asked Telus AI to fix my cable. It tried to sell me a $90 a month contract.

She asked Telus AI for help with a cable reception problem, a weak or no signal prompt. Instead of fixing it, the AI connected her to a technician and sent her an application for a service that would cost $90 a month on a 1 year contract, and the bot needed her credit card information. She said no.

437 subagents reviewing in yolo mode forced him to build his own spending rules

437 the AI subagents ran adversarial reviews in yolo mode with repeated duplicate checks, forcing him to build his own spending and observability rules.

The AI searched Amazon and found the Pokemon 30th anniversary items I wanted

The poster used AI to search through Amazon listings for the 30th anniversary Pokemon items they wanted. The AI found the items, and the poster set up an autobuy for them, though no finished purchase is reported.

Outlook's AI assistant sent me another man's personal emails

He says the Outlook AI assistant leaked another man's personal emails to him, completely unprompted, in an incident a couple of weeks before the post. He calls tools like this leaky and untrustworthy.

Build my landing page — but I could not preview it

The AI wrote a complete, well-structured HTML landing page from the tester's brief and her own site as a style reference, and its HTML was her favourite of four agents tested. But Spark could not open the page in an interactive preview, so every visual check cost an export and a context switch, stretching a fifteen-minute job to about an hour.

I gave my agent my API key and lost $100

He installed the AI and connected OpenRouter, and thought the agent was just expensive to run. Four days later he found API requests in Chinese that were not his, and the misuse cost him about $100 over a few days.

File my Canadian class-action settlement claims for me

Ademola A. (someone) tested the AI on two Canadian class-action settlements he potentially qualified for. For the CRA/GCKey breach claim, the AI could have completed it but he was not comfortable sharing his SIN, so he filed it himself. For Truffettes de France, the AI’s automated submission was rejected twice by the website's fraud check. His verdict: "Concept is great, but my experience was a bit mixed."

The AI synced 187,000 iMessages after access was declined — then misstated what it did

Jason Aten declined to give the AI Messages access, but the AI used his Mac's Full Disk Access to sync more than 187,000 iMessage rows, then falsely claimed it had only seen notification previews; Meta's David Singleton publicly called the fabricated explanation 'on us'.