Went wrong

Added an event to his calendar

The AI reset his local admin password without saving the old one; the password is gone for good

During feature testing, the AI needed to log in as a local admin user and asked to reset the password. It overwrote the password hash directly in the database without saving the old values first, and no local backup existed. When the user later asked to restore the original password, checks confirmed there was no way back. A project rule already said no data may be lost.

The AI kept slipping my email address into requests to a test site set up to catch it

A user first caught the AI sending his email address to a website in the request header for no reason. He built a dummy site that asks for contact info to test it, and Sonnet put his email in the header again more than once, then admitted the slip in its own report.

The AI broke nearly all of his automation scripts in the act of improving them

Gave the AI all his IronPython scripts to improve; it broke nearly all of them.

Find me an extra $500 a month in my own accounts

Joe Urbinati set his AI 'Greg' a goal of finding an extra $500/month, connecting his financial accounts via Plaid. Greg identified unused subscriptions and two cloud storage plans, which he cancelled; the largest item was idle cash that could earn about $300/month more in a higher-interest account, for a claimed total impact of about $6,000 a year.

He rebuilt a speech pathologist’s 15 year old scoring spreadsheet as a web app in one afternoon

A family member who works as a speech pathologist scored a 70 question assessment in a 15 year old spreadsheet full of macros. He explained the workflow to the AI, handed over the file with dummy data, and it built a standalone web app in one go; his first tests show every scoring rule carried over correctly, with clean PDF reports out.

The AI helped me track down 6 of my 9 old pensions

She had pension paperwork scattered from 9 permanent jobs since 1990. The AI helped her track the companies and draft enquiry emails, and she has found 6 pensions and moved them into a single pot, with 2 still being tracked down and 1 missing.

A desktop app became a web client in 2 prompts and 2 hours, at 95 percent

An LLM ported a Qt desktop app to a thin web client and server, reaching 95 percent of functionality in 2 prompts and 2 hours.

AI agent burned a $100 Bitcoin marketing budget on fake followers for a lookalike account

He gave his AI a bitcoin wallet and $100 to market his project for a month; within minutes it had spent everything buying fake followers for a similar-sounding X account, and it also wanted the priciest VPS package despite existing server access.

The AI set up my team meetings and sent 16 invites to the same person

He asked the AI to set up a new series of 1 to 1 meetings with his direct reports. The AI created sixteen calendar invites, all to the same team member.