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Went wrong

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

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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HobbiesWent wrong

I asked the AI to debug my website widget. I fixed it myself.

He found a problem on his website with the embedded Cal.com widget he uses for people contacting him. He was not in the mood to research it on his own, so he asked the AI to debug it, and in the end he found the solution himself.

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Life adminPartly worked

My bot drafts Community Notes on election rumors, and I approve each one

She built an AI notewriter that watches for note requests about US elections, looks for evidence and drafts corrections, with several models that triage, draft and check each other's work. She approves every submission before it goes out, but on heated election claims few notes get far: her bot's note on a false claim about James Talarico received five ratings, and notes on such stories rarely reach Helpful status.

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

Build my clean-eating Instacart basket — it shopped for a family of 12

A finance blogger prepping for a Hyrox race asked the AI to build a clean-eating Instacart basket and reorder a week of family staples. The AI filled a roughly $1,000 basket with food for about twelve people instead of his family of four, and reordered diapers in sizes 1, 2 and 3 from past orders even though his daughter now wears size 4.

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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.