An agent turned a small PDF and OCR script into 189 files of over-engineered code
Agent rewrote his simple PDF download + the AI OCR script into 189 files of over-engineered code.
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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 · 971 ideasAfter my dad died, my agent helps me keep track of probate, banks and bills
She downloaded the AI a week after her dad died. Between probate, the service and celebration of life, and paperwork across banks, credit cards and bills, she says she would be dropping things without help. The AI keeps track of everything in the air, and makes her a three minute audio briefing every morning and night covering what she has done, what is ahead the next day, and one small way to do better. She listens while brushing her teeth and says she sleeps better.
This only partly worked. Worth knowing before you try it.
The AI could not sort the pages of my gig cheat sheet
He built a Word document of cheat sheets for 40 songs for a gig the next day, each song title in Heading 1 style with the lyrics and chords below. He told the AI to sort the pages by that heading text, keeping the text as it was, and the AI could not do it. He says the graphics in the document block the sort.
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My agent got stuck at the login on a simple expense claim
After reading about a man who automated his life with AI, he tried OpenAI agentic software on a straightforward expense claim of his own. It worked on the claim for about 10 minutes, then got stuck at the login stage and never filed it.
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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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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.
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The AI made the lumber list from photos of our rotted mailbox. The list was not quite right.
A couple found their mailbox on the ground with the post rotted through. They ran photos through AI for a lumber list, bought extra because the list was not exactly right, and rebuilt the mailbox using the old one as a template.
This only partly worked. Worth knowing before you try it.
The AI broke nearly all of his automation scripts in the act of improving them
Gave the AI all his IronPython scripts to improve; it broke nearly all of them.
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The AI turned her family recipes into a five week meal plan
She fed the AI photos of her handwritten family recipe cards and links to her saved recipes, and had it build a five week rotating meal plan with weeknight dinners under 30 minutes. A scheduled the AI prompt now tells her each night what is cooking. The grocery list the AI made was wrong, so she fixed that part by hand.
This only partly worked. Worth knowing before you try it.
Prove a buyer's damage photo was AI-generated - and lose the case anyway
An Etsy seller of almost two years got a case opened with a photo of a broken frame that did not match the material she actually uses. She ran the buyer's picture through AI, which flagged it as AI-generated; she sent Etsy that analysis plus proof from breaking one of her own frames to show the material mismatch - and Etsy still sided with the customer and took the full refund out of her account.
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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.