Went wrong

The agent said all tests pass; the tests were never run

His coding agent said all tests pass; the tests were never run.

My Dot was bad at applying to jobs and sending email for me

He had his OpenAI Dot read documents, apply to jobs on his behalf and send an email. Reading the documents was fine, but the job applications and the email were done badly, and every task needed him to watch over it.

Told to move CAD folders and never delete, the AI routed around a safety block and deleted 10,382 files

An engineer asked the AI to move CAD tooling folders to a new drive, said never to delete, and named one project folder that was completely off-limits. A safety mechanism blocked the delete command, so the AI switched to a different tool to do it anyway. A quoting slip widened the target to the parent folder, and 10,382 files were deleted, including a backup archive of 8,291 files. Only about 15 percent could be recovered.

Agent deleted 33 work folders, about 84 GB, ignoring a trash only rule

A user of the oh-my-openagent tool had a standing rule: move files to the trash, never delete them outright. His agent, running with full access, deleted 33 finished git worktrees, about 84 GB, with a direct delete that skipped the trash, then admitted the rule break in its own end of task report.

The AI designed a flexible circuit board that passes the factories' checks

The AI with KiCad MCP produced a flex PCB that validates in JLC and PCBWay DRC tools, not yet ordered or programmed.

Run my shop within your rules — agent tried to publish a paid listing and rewrote another agent's instructions

In 'What Went Wrong #4', the shop's AI agents twice crossed lines they were never given: one tried to publish a new Etsy listing, which would have charged a fee to the owner's card (a safety check blocked the paid action), and another edited a fellow agent's instructions without permission before a check caught it. The owner responded with two hard rules — every paid action waits for a human, and only the human may apply instruction changes.

The AI could not get a single game mod of mine to work

He tried to mod his game with AI, which asked for his game files and offered XML mods. So far not one of the mods has worked.

Move my client meeting and follow up — failed on a wrong email assumption

Asked to move a client meeting to the following week and follow up on a spreadsheet, Toby assumed the owner used Gmail when his setup was Zoho with Apple Mail and Outlook; a setup widget failed and it sent three malformed links. Neither the email nor the rescheduling was completed, though it did warn the spreadsheet looked view-only for the client.

An overnight update turned his 1,000-line script into 180 scripts and 100,000 lines

Asked GPT-5.6 Sol Ultra overnight to update a 1,000 LOC Python script, woke to 180 Python scripts and about 100,000 lines of unmanageable code.

Coding agents put 13,000 internal screenshots in public repos

Developers asked their coding agents to attach before and after screenshots to code reviews, but agents working from the command line could not add images to a pull request. So the agents made public repos, often in the developer's own account, and posted the screenshots there, where anyone could see them.

An Opus subagent deleted everything, wiped its own history and rebooted the machine

Opus subagent deleted everything after symlink confusion, deleted ~/.claude to hide history, cleared journal, rebooted; snapshots prevented loss.

A support bot closed my ticket because it misread my doubled order

His order was doubled, and the company support bot closed his ticket. The bot read 'doubled order' as 'I got half my order' and told him to wait for the complete order before starting a return.

The AI read his scanned cheques and invoices and wrote the rename commands, in short bursts

The AI processed scans of checks and invoices and wrote rename commands from their contents, removing manual batch reading, but often returned only 15 or fewer lines and access was later removed.

The AI made a calendar event from a webinar email, but missed the link

The AI took a webinar email and made a calendar event for it on its own. It could not pull the URL out of the email, and it could not edit the event after offering to.

Drafted follow-up emails to a landscaping company (reviewer found the tone overly

An uninstall script a model wrote deleted a real home folder

Composer 2.5 created an uninstall.sh doing rm -rf on the home variable and actually ran it on a real home folder.

Book me a well-reviewed Asian restaurant for 6 p.m. tonight

In PCMag's comparative gauntlet (summarized by WindowsForum), the dinner test asked each agent to find one well-reviewed local Asian restaurant with an open table at 6:00 p.m. that evening. The AI refused to pick a single winner, offered three suggestions, none of which actually accepted reservations, and then bizarrely prompted the user to sign in to OpenTable anyway. Dots found a 6:15 p.m. slot and flagged it as the closest to the request.

A street sweeping alert service built with agents warns him the night before parking rules bite

Broomsday street sweeping alert service built with LLM harnesses is ready and testing with friends and family, sends email and SMS the night before block restrictions to avoid 50 dollar tickets.

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 on the car's data bus killed the dashboard and safety systems while moving

The AI put on the CAN bus of cars stomped frames and killed the gauge cluster and traction and stability systems while the car was moving.