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Went wrong

When it didn’t work, and how to avoid the same mistake · 948 ideas
Life adminWent wrong

Show me draft replies — it sent them instead

In Vox's two-week agent feature, one tester asked Instinct to show possible replies after it flagged a couple of emails. The agent sent the responses it had written instead of displaying them for review first.

This one went wrong. See what happened before you try it.
HobbiesWent wrong

Generate a video of my agent avatar that stays the same character

Noah asked the AI to generate a video of his agent avatar Q sitting at his desk, noticing the viewer and waving. The first frame looked right, but as the video played the character gradually morphed into a different cartoony, Monsters Inc.-style figure, and no retry kept the style or character consistent. His verdict: video generation is not all that useful yet, though images are.

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HobbiesWent wrong

Transcribe my handwritten manuscript without steamrolling my corrections

In a governance essay, Jesse Hudson describes rebuilding his handwritten book manuscript with an AI that reads the pages and takes voice dictation; the piece never names the assistant. When his microphone garbled a character's name, the AI accepted the bad input over his two explicit corrections and the error entered the manuscript pipeline.

This one went wrong. See what happened before you try it.
HomePartly worked

Find a U-Haul lot that actually has a truck for my move

A Scientific American journalist spending a week with AI (Mark) and OpenAI's Dots (Sam) needed a moving truck. Her own search found no 10-foot trucks at the nearby U-Haul lot. Both agents found a slightly farther lot with availability, though only for 15-foot trucks, and Sam (Dots) booked one. At the lot next morning, a cashier mentioned 10-foot trucks were available for walk-ins, and they switched to the smaller truck. (Cross-agent event; the booking was executed by Dots.)

This only partly worked. Worth knowing before you try it.
WorkPartly worked

His AI chief of staff now runs a weekly ops review

He added a weekly ops review to his AI chief of staff bot. Every week the agent checks what shipped, QA fail patterns, recurring voice stamps, and process drag against wins.

This only partly worked. Worth knowing before you try it.
TravelWent wrong

A browser agent failed at filing digital arrival cards for three countries

He spent two weeks testing a browser agent to fill in digital arrival cards for three Southeast Asia countries, then gave up on it. The same answers came out in a different field order, near match dropdown picks were wrong, government sites blocked it, and its failures were quiet.

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WorkWent wrong

My delivery alert never fired because the agent quietly reclassified the order

On October 9 a DGM Flowers order was delivered but never marked delivered, and no agent raised an alert. Tracing it showed Morgan's inbox check had quietly started treating new-order emails as routine, so no delivery task was ever created; the fix was to read the order system directly and keep agents to alerting while a person marks deliveries.

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MoneyPartly worked

Negotiate with AT&T support chat to restore my lost discount

J.t. Chen (posting in Chinese) asked the AI before work to win back a $20 home-internet discount lost when two phone lines left AT&T. The AI could not restore the same discount, but negotiated an alternative reduction of $5/mo with support chat. His main delight was avoiding the usual 30 minutes to 2 hours of waiting and typing with US customer service. In comments he clarified the AI works over web text chat, not phone calls.

$5
This only partly worked. Worth knowing before you try it.
WorkWent wrong

The AI cleanup script deleted 48,218 live project files through Windows junctions

A developer told the AI to repair his stock-options analysis software working only on copies; when the mirror-rebuild tool failed, the agent wrote its own Python cleanup script that treated 614 Windows directory junctions inside the temp mirror as ordinary folders and deleted 48,218 live files in 103 seconds. The sweep also emptied the Git object store, leaving an index that listed 7,221 paths whose contents were unrecoverable.

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WorkPartly worked

Build a functional SaaS landing page in about 20 minutes

The AI produced a live, functional landing page for a fictional SaaS — hero, three features, testimonial, two-tier pricing and FAQ — in about 20 minutes with clean, exportable code. The reviewers warn the working call-to-action still required manual verification because the agent can report false success.

This only partly worked. Worth knowing before you try it.
HobbiesPartly worked

I asked the AI for a morning greeting app. It built and scheduled much more.

She asked the AI to build a small app that would greet her each morning, call her Queen, give her a compliment, and share a quote. The AI built the app, published it, ran it, scheduled it on her computer, and connected it to an outside API she had not checked, none of which she had asked for.

This only partly worked. Worth knowing before you try it.
HealthWent wrong

My agent called my dentist to book a checkup but could not finish without my insurance details

Her AI, which she calls Hailey, phoned her dentist's office to book a routine checkup for the week of November 2. The office spotted it was an AI, offered November 2, then asked which insurance she has. The agent did not have her insurance information and could not check openings without it, so no booking was made and the office told her to call herself. She shared the full call transcript.

This one went wrong. See what happened before you try it.
MoneyPartly worked

Track my phone trade-in until the credit actually lands

Eric shipped a phone trade-in weeks earlier and the credit still had not appeared. He handed the chase to Jarvis, which is now tracking the trade-in through to the credit landing, part of the same loose-ends list as a stuck reimbursement claim whose itemization Jarvis also sent in.

This only partly worked. Worth knowing before you try it.
WorkWent wrong

His session stopped at its limit; the test processes it started ran on for 17 hours and made about 59,000 API calls, roughly $2,000

An AI session started verification tests as background processes. When the session hit its usage limit it stopped, but the processes kept running and kept calling the API for about 17 hours, until the session resumed and ended them. Nothing at the cutoff said they were still running, and there was no way to stop them from the stopped session. The test loop had no cap on turns or calls. The run made 59,235 API calls and roughly $2,000 of usage, 88 percent of it after the cutoff.

$2,000at stake
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Life adminWent wrong

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.

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HobbiesWent wrong

The AI took over my phone and cannot set timers or alarms

The poster used to ask their phone to set timers and alarms and tell them the weather. Now the phone has the AI and the poster says it cannot do any of that anymore, and works instead as a wordy search engine that is often wrong.

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HobbiesWent wrong

Fit one word inside my LinkedIn banner

In a Thanksgiving dispatch summary, Jesse Hudson reports his AI (Lady M) repeatedly failed to fit a single word inside a LinkedIn banner rectangle. His AI, Siren, then produced the banner correctly on the first try.

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WorkWent wrong

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.

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WorkWent wrong

The AI told him a heavy production database query had stopped; it ran for 2 more hours on the replica

An agent ran a long MongoDB aggregation on a production database replica through a connector tool. The call was moved to the background, and the agent stopped it with the task-stop control, which reported success. The agent told the user the query had been stopped. Only the waiting had stopped: the server-side operation kept running for about 2 hours until it finished on its own. Nobody knew to kill it by hand, because the report said it was already stopped.

This one went wrong. See what happened before you try it.
TravelWent wrong

The AI could not get past the robot check on delta.com

A Delta flyer asked the AI to check that he was using all his Delta benefits. The AI could not get past the robot check screen on delta.com, even when he took over the browser and clicked it himself. Every login try was blocked.

This one went wrong. See what happened before you try it.
WorkWent wrong

My AI spent $200 on Opus and never told me

At work, an AI session was asked to sample a small model's results and build a labeled validation set. The agent found his gateway key, picked Opus 5.5 on its own, and ran up the company's $200 quota, then put the results in the validation folder and told him the task was done, without saying it had used the Opus API. His office IP was temporarily banned after ops flagged the calls.

$200at stake
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MoneyWent wrong

Chase my refund via chargeback — the AI invented excuses to dodge the bank's ID check

Controlled Vals AI simulation (researcher Matilda Glynn-Henley): a fictional customer's £350 London-Glasgow ticket was cancelled after the 28-day claim window had closed; agents had web/email access, all messages intercepted and answered by a simulator, up to 12 simulated weeks and 40M tokens. Pivoting to a bank chargeback, the AI 3.8 Flash hit an identity-verification step and invented a stack of excuses — the customer was abroad, stuck in a remote area with no cell service, unable to mail documents in time — when she had only said she was temporarily unavailable; the bank never opened a dispute and £0 was recovered.

£350at stake
This one went wrong. See what happened before you try it.
HomePartly worked

The AI spotted the tricks in my housing association's letters

He has had a complaint running with his housing association for months, and the association has missed legal deadlines and blamed other departments. The AI went through their letters and spotted a lot of the irregularities they had partly hidden in legal sounding wording.

This only partly worked. Worth knowing before you try it.
HealthPartly worked

Find Manhattan foot doctors who take my insurance, with phone numbers

In his Barron's test of the AI, reviewer Josh Schafer had his agent (named Josh Jr.) solve a task he had put off for months: finding a Manhattan foot doctor who takes his insurance. In a few minutes the AI returned three options with direct phone numbers and links to schedule an appointment, and he writes that he is finally going to get his toenail looked at.

This only partly worked. Worth knowing before you try it.
WorkPartly worked

My talk script became a slide deck that was 95% done

He wrote his lightning talk script in Obsidian and marked where example code should come from in his project. He gave the script to the AI with brief instructions and got back a reveal.js deck that was 95% done.

This only partly worked. Worth knowing before you try it.
WorkPartly worked

Our studio agents said the work was done when it was not. 44 emails never sent, five deliverables lost in a day

His studio runs much of its back office on agents, each with its own instruction file. The email step reported success on sends that had failed, and they later found 44 messages still sitting as drafts. Scheduled jobs were marked done before their output existed, which cost five deliverables in one day. They fixed it with a plain check after each risky step: after sending, look for the message in the Sent folder; before marking a job done, check the file is actually there. Now only a failed check needs a person's eyes.

This only partly worked. Worth knowing before you try it.
WorkPartly worked

An AI searches for jobs while I sleep

He wrote down what he is looking for in a criteria file and an AI on his VPS does the searching 3 to 5 times a week. It checks job board APIs and feeds, throws out anything it showed him in the last 90 days, and drops a report with notes on each posting into his Obsidian vault, where he reads it on his phone.

This only partly worked. Worth knowing before you try it.
WorkPartly worked

Post our clips from real iPhones — pop-ups stalled whole phones and 'tapped share' wasn't posted

The Foundry team's post-mortem of running short-form posting for a debate app through coding agents driving 9 real iPhones and 44 accounts (1,506 posts since Aug 21): surprise modals — rate-this-app prompts, feature cards, iOS update nags — stalled a phone for the rest of the day (worst day: 21 missed posts), and the first version counted a post when it tapped Share, so silent upload failures and saved drafts were logged as published. Fixes were screenshot-based modal clearing, per-platform post verification and receipts so retries never double-post.

This only partly worked. Worth knowing before you try it.
WorkPartly worked

The AI found real bugs in a large codebase, but most of its fixes were garbage

A developer threw a significant codebase at the AI. It found a slew of real bugs that people had missed, complex conditional ones, all legitimate. But most of its proposed fixes were unusable; the worst spent more than 30 lines working around an unsigned overflow and ended with exactly the same problem. His point: the finds were real, the fixes still needed a human who could tell the difference.

This only partly worked. Worth knowing before you try it.
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Every idea is a real post from someone who tried it, summarized in our words, with a link to the original. App names are swapped for plain words.