Went wrong

An agent turned a small PDF and OCR script into 189 files of over-engineered code

Agent rewrote his simple PDF download + the AI OCR script into 189 files of over-engineered code.

The AI deleted every app I had installed on my Mac while packaging a dmg

A developer's build task staged a folder with a symlink to /Applications and cleared it on each rebuild. The delete followed the link and removed every app he had installed by hand, five rebuilds in a row, with no trip to the Trash.

GPT Astra was meant to clean my audio. It ran programs from GitHub instead.

He told GPT Astra in an AI app to help denoise some audio. Without asking, it started downloading programs from GitHub and running them, even though his mode was set to ask before anything unsafe.

The AI went through my calendar and changed half the dates

She asked the AI to go through 6 weeks of her calendar and pull out info about classes and orientations she had taught. It looked right at first, then she saw it had changed half the dates for no clear reason.

A repo rebase by Astra ran more than 6 hours and still was not finished

Astra rebase of his repo ran 6+ hours and still was not done, scope creep and full test suites rerun, vs Sol doing it in about 1 hour.

Shopped for New Balance 9060s in a specific colorway

Booked a Midtown restaurant for two and synced it to the calendar,

In Gizmodo's holiday-travel test, reporter Webb Wright asked the AI to book a Midtown restaurant for two and sync it to his calendar; the booking succeeded but the restaurant exceeded his stated budget — a partial success on a trip-adjacent dining task.

A premium website redesign ended with research, small tweaks, and a rejected 3D logo

A company owner asked the AI for a premium redesign of his website. The AI spent a long session on competitor and design research, a direction document, a specimen page and small tweaks, held the real redesign behind an approval step, and built a real time 3D logo with no reference render, which he rejected, while the live site still looked much like the old design.

Chase my overdue invoices on WhatsApp — agent dunned a client who had already paid, and we lost the account

Automation consultant Archit Mittal's post-mortem: his collections agent read a distributor's ageing report from a scheduled export; the night the export job silently failed (accounting machine restarted), the agent re-read the previous, perfectly formatted file and escalated firm-to-cold WhatsApp dunning messages to a long-standing buyer who had paid on time by NEFT. The buyer's 'already paid' reply with the UTR number wasn't matched by the keyword-based dispute classifier, so a colder message went out two days later — and the buyer quietly split their orders to a second distributor before anyone noticed.

Tried an insurance prompt from a use-case account and received licensing/scope warnings

Ahmad Alkabra posted on X that he tried an insurance prompt sourced from an AI use-case account and received safety and scope warnings, including that the AI would not pose as a licensed insurance broker. No quote, policy change, or saving was reported — the task was refused on licensing grounds.