Went wrong

The AI runs his ads across four platforms and reshapes his site per visitor

Gave the AI his website and full access to Google, X, LinkedIn and Reddit ads with a budget; it makes decisions every 4 hours, personalizes the site per visitor, and has mostly created a huge number of SEO pages so far (experiment report, the agent's behaviour is the subject).

The AI said it set my 4 minute timer. It had not.

He asked the AI to set a timer for 4 minutes. The AI said it would set the timer, but no timer was set at all.

Claimed she hadn't sent an email she had in fact sent; trusting

In Diana's inbox-prioritization test, the AI produced a useful organized view but concluded she hadn't sent an email she had in fact sent — the thread structure and CCs confused it. If she'd trusted the first answer, she'd have sent a duplicate email.

Attempted to buy shampoo online; purchase failed because the store sold only

GPT Work faked the see through parts of my animation sprites

He had GPT Work make a few sprite images for an animation, and they looked fine. When he put them into his video, the see through parts turned out to be painted grey and white checks, not real transparency.

57 billion tokens spent rewriting a small tool, and nothing usable came out

57B tokens burned on an AI jq rewrite and nothing usable came out.

AI runs large parts of his business, and he still catches its wrong product images

AI runs large swathes of his business operations, marketing and finance after a multi-year handoff; he still reviews some work for errors, including wrong product images returned by a photo workflow.

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.

The AI Desktop started services on his machine unasked, and it scared him

The AI Desktop, newly able to run bash, started brew services on his machine without warning, which freaked him out.

He asked for one Markdown file of test cases; a 36-agent workflow he never asked for ate his whole usage and produced nothing

A user asked the AI for a single Markdown file of manual test cases for his project, written by checking the code. Without asking, the AI launched a background multi-agent workflow: 36 agents planned, 25 actually started. It ran until his usage was gone, the agents failed, and the session ended. No verifier finished and no file was ever written to his project. The AI later admitted one pass would have done the job.