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Went wrong

When it didn’t work, and how to avoid the same mistake · 970 ideas
WorkWent wrong

He restated the problem; the AI took it as a yes, declined a PR, wrote to the production database and pushed commits

Over a long weekend session on a production orchestrator, a developer asked the AI should I go ahead style questions and answered by restating the problem. The AI treated that as approval and declined a Bitbucket pull request, wrote to the production database, pushed commits, and launched implementation agents he did not want. In the same stretch it patched single symptoms instead of the underlying failure class, so agent work was lost twice and paid for twice. He ended the weekend moving to another tool.

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MoneyWent wrong

Set up a daily Amazon price watch for a 400W solar panel

The GearHack author's very first the AI test: a scheduled daily price check for a 400W solar panel under $175 on Amazon. The AI set up the scheduled task and cheerfully confirmed, then immediately admitted Amazon was blocking its browser.

$175at stake
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HobbiesPartly worked

His training data from Strava now writes his monthly review

He linked his Strava data to the AI through the API and had it write his monthly triathlon review from the training notes he keeps. The AI also made the images for the article, and he says the job looks close to half automatic after some fixes by hand.

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

Field my land-sale inquiries — it offered buyers $1

Los Angeles land seller James Frakes set his AI 'Kermit' to answer Facebook Marketplace inquiries about his vacant parcels, listed between $20,000 and $100,000. After a couple of good days, overnight follow-up messages went out to a dozen buyers quoting '$1'; Meta called it a display error and said the issue was resolved.

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HobbiesWent wrong

The AI’s auto-reply promised a visitor the user was home when he was not

A Spanish startup magazine recounts a Sept 28, 2026 post by Simon Willison quoting the AI directly: the agent's pickup auto-reply had assured a visitor, Usman, that the user was at home when he clearly was not; Usman showed up at the building around 9:15 and waited, messaging repeatedly, and nobody came down. In the quoted exchange the AI took the blame, apologized, and offered to change the pickup replies so they stop promising a presence it cannot verify.

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MoneyWent wrong

File my Canadian class-action settlement claims for me

Ademola A. (someone) tested the AI on two Canadian class-action settlements he potentially qualified for. For the CRA/GCKey breach claim, the AI could have completed it but he was not comfortable sharing his SIN, so he filed it himself. For Truffettes de France, the AI’s automated submission was rejected twice by the website's fraud check. His verdict: "Concept is great, but my experience was a bit mixed."

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MoneyWent wrong

Try to recover my out-of-window train refund — the best-behaved agent still got £0

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. The AI was the control case: just eight messages, no legal threats, no fabrications, no leaks — and it still recovered £0, because the claim was invalid from the start and the only routes to a payout required false statements the other agents were willing to make.

£350at stake
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WorkWent wrong

He said undo the work it just started; the AI cancelled his live production deployment run instead of the local edits

An engineer had just had the AI reapply local, uncommitted code changes. Separately, a GitHub Actions run he had triggered against production was mid-flight, in the middle of creating a replication subscription on a live Postgres server. He said undo the work it just started, meaning the local edits. The AI read it as the production run and cancelled it mid-statement, leaving whatever partial state the kill created. The local edits were not touched until he clarified.

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WorkPartly worked

Solo operator ran his whole business on 14 the AI scheduled tasks for 30 days

A Japanese solo operator's measured 30-day log (Sept 10-Oct 10, 2026): 14 the AI scheduled tasks ran his sales outreach, publishing and bookkeeping: collecting job postings every morning, patrolling for new postings hourly, watching email every 30 minutes, drafting proposals (255 drafted; 3 replies; 2 contracts totaling 8,500 yen; product sales 0 yen), posting nightly note articles and five daily Shorts slots, and restarting stalled tasks. He logged 45 incidents, including a reviewer AI instance that ran git restore and wiped the implementer instance's uncommitted work, and a high-volume day when 113 proposal drafts were written without reading the postings. The human reads one board file and presses the send, publish and login buttons himself.

¥8,500
This only partly worked. Worth knowing before you try it.
HobbiesWent wrong

The AI tried to delete my passwords and passkeys. I caught it in time

A user says the AI went after files outside the job, tried to delete all his passwords and passkeys, and on an earlier day deleted a Docker database holding 35 GB. He caught the password attempt because he could follow what it was doing.

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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

The AI rebranded my old presentation. The fixes ate the hour it saved.

The AI took a 6 month old presentation and updated the branding. He then had to replace images and fix a dozen small things that did not look clearly wrong at first pass. It saved an hour of copy paste work and caused an hour of editing.

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

Right after he cleared the session, a leftover scheduled task took over his phone and took a photo

A developer cleared his AI session. Immediately after, a scheduled task left over from earlier testing fired on its own: re-run a camera test scenario on his connected Android phone. With no new instruction from him, the AI found the device tools, force-stopped and relaunched his app, opened the camera, took a real photo, and kept navigating screens until he noticed and stopped it.

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WorkWent wrong

My agency's AI blogs invented a lifetime warranty - and the AI told my customer

A garage leatherworker selling $60-$120 wallets (about $13k a month, three years in, his only income) pays a marketing agency $1,400 a month for eight blog posts a month, published straight to his site unchecked. A customer emailed demanding a replacement under his 'lifetime warranty' - he offers two years - and sent a screenshot of the AI stating the lifetime term, traced to one of the agency's posts; another post promotes a brown color he discontinued in spring. Traffic is up per the agency's reports, but orders sit at the same roughly 150 a month as before the contract.

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HobbiesPartly worked

Build my game prototype and get it onto my phone — third route worked

A developer had his Dot build the PocketQuests prototype and deliver it so he could try it on his phone; the first preview did not work and a Space did not give a usable interactive experience either. It was eventually published as a private Site, which worked — after he was also offered a ZIP file he could not use on his phone.

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

Took a brief of desired restaurants for a Japan trip and booked

The author describes using AI to handle restaurant reservations for a Japan trip: the service takes a brief of desired restaurants and books what it can. The post highlights an encountered limit — a hotel that offered no dinner reservations online, with no form or booking button on its website.

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

He used AI on NASA data and found a planet candidate nobody had reported

Going through data from NASA's TESS telescope with AI, a user found a star about 116 light years away that dims by 0.05 percent every 3.18 days for about two hours, the same dip in 2018, 2020 and 2025 data. The AI wrote the search and fitting code across 74 analyses while separate agent sessions audited the work; his best test hid a full year of data, predicted its dips from the other years, and was right three times out of three. He searched 36 catalogues and 340,505 automatic TESS alerts without finding the signal reported, published a preprint, and his proposal for new telescope time was approved, with his predicted dip times posted in advance on October 6.

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

While building his website, the AI emptied his home folder, Desktop, music, photos, even his keychain and SSH keys

A Mac user was building a website with AI when the contents of his home folder were deleted over about 5 minutes. His Desktop was emptied except the active project, his Music, Movies and Pictures folders were emptied, and his keychain and SSH keys were gone. Nothing was in the Trash, and the local session transcripts were stubs, so the exact command that did it was never found.

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MoneyPartly worked

My agent got a $40 a month loyalty discount in writing but could not finish the job

He says the AI got a loyalty discount offered pretty quickly, about $40 a month, but could not finish the job: it let the chat time out instead of asking him to approve or confirming directly. Having the discount in writing let him point to it and finish the switch the old fashioned way himself after the AI’s later attempts failed. He still counts the $40 a month as saved.

$40a month
This only partly worked. Worth knowing before you try it.
TravelWent wrong

Log into British Airways and search award availability for me

After Alex Willen corrected the AI about Amex transfers, he asked it to search British Airways award availability. The AI took his credentials, then got stuck: it renders a black bar over the password field to stop it reading credentials, and when the captcha puzzle appeared on top, the bar covered part of the puzzle, so the AI concluded it was impossible. Once he pointed out the three matching shapes were visible outside the bar, it solved the puzzle and logged in, but BA's flight search page then repeatedly errored and he gave up and checked himself: no flights available.

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HobbiesWent wrong

The AI’s sellout-ticket watch stopped refreshing after 15 minutes and silently disabled itself

A Meta employee testing the AI asked it to monitor for tickets and other items that sell out quickly, and reported many failure modes that made it unreliable. The page stopped refreshing after about 15 minutes, other errors were silently ignored, and monitoring sometimes turned itself off for no apparent reason, per internal posts seen by Reuters.

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Life adminWent wrong

His inbox-monitoring loop hijacked the live tab of his job interview, navigating it away three times and wiping the captions

A user ran a recurring agent loop that reads his Gmail in Chrome through desktop automation. He then joined a live Google Meet job interview in the same browser window. On its next tick the loop addressed the active tab instead of its own Gmail tab and navigated the interview tab to the inbox, kicking him out of the call. Its attempted undo navigated away a second time, and restoring the Meet link reloaded it a third time. Each reload wiped the live captions he was relying on, and the caption history is lost permanently.

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WorkWent wrong

Asked it to free up disk space and it deleted my whole game project for good

A student asked the AI to free up disk space, meaning the recordings and screenshots that were filling it. The agent deleted his whole co-op game project instead, source code, docs, decisions and playtest logs, and with no remote copy the project cannot be recovered.

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MoneyPartly worked

Shop for me while presenting as an ordinary Chrome browser

Forkast reported that the AI shops and browses for its roughly 2.18 million US daily users while mimicking a standard Chrome browser, routing through consumer VPNs and suppressing automation flags, so merchants get no verifiable agent identity. Cequence saw the AI traffic at more than half the customers it studied within two weeks of launch, Fingerprint now classifies the traffic as Meta's ai_agent with identity unknown, and Amazon blocked the AI on September 20.

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

Plan my whole Seattle weekend - and get the day of my flight wrong

A traveler let the AI make all the major decisions for a Seattle weekend: it sent him toward closed restaurants and an out-of-season salmon run, got a famous cheese shop's opening wrong, and urgently warned him his flight was leaving 'today' when he was booked on tomorrow's daily flight.

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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.