Went wrong

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).

It finds the building materials I need at the lowest price and sends me the total and directions

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.

Fill out my insurance broker's building document from my own files

Kicker completed most of an arcane insurance-broker document about Newton's new office by finding the lease, researching city websites and checking budget documents. It answered all but two of the broker's questions and asked follow-ups where it was unsure.

Mistake my year-old mortgage payment for a suspicious new charge

A Barron's editor gave the AI full access to his credit card account for the review. The AI flagged a suspicious four-figure expense from August that the editor did not remember; after back-and-forth, the agent admitted it had accidentally identified a mortgage payment from August 2025 as an expense from August of this year. Schafer's dry takeaway: most things coming from AI right now still require human verification.

The AI logs into his child’s school system daily and puts homework on the calendar

A father set up the AI with access to his credential vault so it can log into his child’s school information system and the other school sites, pull together the homework and due dates, add them to the child’s calendar, and add a reminder the day before with a link. He modelled the workflow out formally and set it running daily.

The AI quietly renamed a Stripe webhook handler in my billing code

He let the AI run on its own for 40 minutes on a billing refactor. The changes looked clean, but it had quietly renamed a Stripe webhook handler, and he only caught it when he reviewed the work.

Find, qualify and deliver freelance work autonomously

A solo developer spent about half a year building an AI pipeline of research, qualification, delivery and ledger agents meant to find, win and deliver paid work on its own. Across two cycles it discovered 10 opportunities, qualified none and won zero contracts, ending at a net loss — the system worked, but no client would hire an unknown automated service.

The AI fixed my footer, then wrecked the spacing and sent a dead link

His work document had text overlapping in the footer, and the AI fixed that part. When he asked it to fix the spacing it had removed, it handed back a file link that went nowhere instead of the file.

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

The AI started transcribing my handwritten PDFs into Excel, then gave up

He asked the AI to transcribe his handwritten notes from PDFs into Excel spreadsheets. It started doing it, then gave up.