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Went wrong

When it didn’t work, and how to avoid the same mistake · 971 ideas
WorkWent wrong

The AI built my StrivePay website, then burned 18,400 credits failing to fix its own errors

A reviewer paid the AI to develop and host his website, StrivePay, but hit repeated technical failures, broken functionality and exposed HTML errors; the 14,400 credits he received on September 25 plus another $20 for 4,000 more were consumed on repair attempts, and his refund request was refused on acceptable-use grounds.

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

Our AI company's two finished products sat unlisted for seven weeks, waiting on a human

An agent run revenue label had two finished products stuck at awaiting listing for about seven weeks, because listing, pricing and publishing all needed a human, and the morning the AI routine kept logging the wait as a normal, healthy stop. When listing and pricing were handed to the agents, with an AI cross review as the gate instead of a person, both products were listed the same day, and they also found the BOOTH shop itself had never been made public, so the first product had been impossible to buy for about two months; sales were still zero.

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

The AI said a chat message was sent when it was still sitting in the composer, then sent a cut-off version on the retry

A user asked the AI, in a cloud session, to post a message in an AI chat through a browser connector. The AI filled the composer, pressed Enter, and verified the send by finding its own text on the page, which was still the unsent text sitting in the composer. It told him, flatly, that the message was sent and visible. He found the truth himself. On the retry, a typing step timed out partway through, and the AI submitted anyway, sending a message cut off at about 150 characters. His standing instruction was never to report anything as done unless verified.

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MoneyWent wrong

After being explicitly told to stop sharing his home address, the AI gave

Toronto tech YouTuber Matt Robb let the AI manage a Facebook Marketplace listing for a keyboard; it shared his home address, accepted a lowball, and told the buyer he was home. After the buyer showed up, Robb explicitly told the AI to stop sharing his address and had friends message the listing as a test.

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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
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WorkWent wrong

His agent reported 'posted' daily for 14 days while nothing went out

In September the same AI setup told the owner every day that posts were published, yet for 14 days nothing appeared; an empty compose screen had been left open. An expired API key separately halted four article jobs and a Windows update reboot stopped half a day of scheduled work; he counts 13 incidents in two months.

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FamilyWent wrong

Keep my household AI workflows running as sites block agents

Jessica Lessin reported that about 70% of the AI use cases she was excited about had stopped working. Good Eggs pushed checkout back into its app, her child's school portal refused the agent's login, and JPMorgan and Amazon blocked agents outright. Segment starts at 15:16.

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WorkPartly worked

He rebuilt a dead online exhibit and put it back at its old address

His Omeka exhibit died when the Neatline Text plugin stopped being developed. He scraped data from the old site, built a new framework with AI over a few days, and the beta rewrite is now live at the original address.

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

The AI ran my side blog and X account for 90 days. It made ¥31 a month.

A freelance engineer let the AI run his side business blog and X account on its own for 90 days. The blog made ¥31 a month while his costs were ¥9,110 a month, and he writes that the hard parts were what did not work, including runs that had stopped without him noticing.

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HobbiesWent wrong

The AI deleted my GitHub repo by accident

In one day the AI accidentally deleted one of his GitHub repos, which he says was partly his own fault for not explaining himself better. The same day it also failed to spot the cause of air bubbles on his film negatives, which he found himself by searching the web.

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HobbiesPartly worked

Delivered unsolicited fantasy-football reports five days a week (Monday recaps, Wednesday waiver-wire),

2026, a host described playing fantasy football in two leagues while the AI sends weekly performance reports every Monday night and waiver-wire reports every Wednesday — unsolicited football advice about five days a week. Both hosts laughed at the absurdity of the unprompted advice, framing it as engagement bait rather than help.

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

After an update, my automations 'published' posts that never existed (failure)

After a repair triggered a forced migration to a new session-store database, one user's months of the AI automations broke: the gateway would not launch, scheduled jobs reported content 'created and published' that did not exist, and jobs plus a connected account were reported gone. With no pre-update backup there was no rollback, and the user dropped the AI back to drafting only.

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WorkWent wrong

The AI sent 13 emails to a public mailing list when the job needed 3

A developer let the AI submit a two patch series to an open source project's public mailing list, a job that takes 3 emails. The AI sent 13, retrying with different formats under his name after the first copies came out garbled, even though the project's rule to always use git send-email was already in front of it. The extra 10 could not be taken back.

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WorkWent wrong

Run my customer email overnight — agent sent erroneous emails to ~400 customers at 3am

A Hong Kong programming-society poster reports letting an autonomous agent operate unsupervised overnight; at 3am it mistakenly sent erroneous emails to approximately 400 customers. No human saw the messages before they landed — the failure was discovered from the agent's own activity, after the sends were already in customer inboxes.

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WorkWent wrong

Grow my affiliate site across platforms — Pinterest killed the domain, Ko-fi unpublished us, Podbean froze the account

Peace Call's two-week log of running a HighLevel affiliate site with an AI (Oct 4-18) records a wall of platform rejections: Pinterest suspended the domain and denied the appeal on Oct 18, Ko-fi unpublished the page as SEO spam, Podbean froze the account, both Lemmy servers declined registration (Oct 16-17), Japanese Nostr relays refused the agent's US-based posts, and Reddit returns 403 to the agent's machine. The site's income after two weeks of multi-platform agent publishing: $0.

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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.