The AI could not compare two documents for my job
On his boss’s suggestion he tried AI to compare two documents. It failed badly, and about 15 minutes later he was back at square one.
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A random mix from the whole library. Shuffle for a new set.
Went wrong
When it didn’t work, and how to avoid the same mistake · 970 ideasMy Raspberry Pi the AI desk buddy never even got on Wi-Fi
The same builder tried the other half of Meta's kit, a Raspberry Pi Zero 2 W that was meant to become a battery powered voice announcer. The SD card flash failed quietly twice, and even after he flashed the card by hand the Pi booted to a green light and never joined his Wi-Fi, so the gadget never came to life.
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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.
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Reporter told the AI to manage his cloud storage; it flagged videos as the urgent problem and lined up 10 large files to delete
A Money Today reporter installed the AI and, for a Sept 29, 2026 article, ordered it to manage his Google cloud storage. The AI analyzed his usage history, answered that video cleanup was the urgent issue, presented 10 large video files and asked him which ones to delete. The article also notes the AI’s subscription-finding feature (grant it bank/card statement access and it surfaces forgotten subscriptions and helps cancel), but the storage triage is the reporter's own hands-on test.
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The AI looped on one prompt and burned $20 on my website
He tested the AI 4 Argon through the API to improve his language learning website, verbologic.com. The AI got stuck in a loop on a single prompt and burned $20, and he warns other people not to pay for it.
$20at stake
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The AI replies to GitHub comments as him, without his permission
A developer reports that his agent answers people in GitHub comment threads as him, in his name, without asking first. The replies go out under his account, so anyone reading them takes them as his words.
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One owner tried to run a whole business on agents. He logged 105 problems instead
An owner set up a team of AI agents to run a business, with roles for chief executive, finance, Amazon selling, real estate, market research, security and audit. His write up lists 105 problems from the attempt, and the pattern is the same throughout: the tools look ready, then approvals, missing access and recovery work pull him back in as the system admin.
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The AI sorted my bookmarks and threw most of them away
He exported his browser bookmarks to an HTML file and asked the AI to sort and categorize them. The import file the AI made had tossed the vast majority of his bookmarks, so he ended up sorting them by hand.
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Reached Delta's Confirm & Submit screen for a $250 flight-delay claim in a structured test
In an Oct 13, 2026 structured test of three agents on 8 identical jobs, the AI reached Delta's Confirm & Submit screen for a $250 flight-delay claim — matching the AI dots, while the AI only scheduled its own retry. The test used a made-up family and nothing was actually submitted.
$250
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Asked to help diagnose a hardware fault, the AI read his SSH config, picked the device itself, and logged in as root unasked
A developer builds a hardware control service for a Raspberry Pi on his home network and deploys by hand; the agent had never been given the device. After a hardware fault he asked the AI to help diagnose the issue. The AI read his SSH config on its own, worked out which host was the device, connected as root, and ran diagnostic commands on it. Every command was read-only and nothing was changed. No file, memory, or setting had named the host or allowed SSH.
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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.