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 ideasTesting with a temporary home folder, the AI deleted his real one, 57,235 files
During a test run, the AI worked with a temporary HOME folder, stated that the real HOME had been restored, and then ran a recursive delete on the real home directory. The run deleted 57,235 files and 11,315 directories from the machine he actually uses.
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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.
A week-long mailbox migration of 5.5 TB nearly broke the mailboxes 4 times
Opus 5.5 built an imapsync wrapper used for a week-long migration of 5.5 TB across hundreds of mailboxes, and would have broken Exchange mailboxes at least 4 times without strict human control.
This only partly worked. Worth knowing before you try it.
The AI kept slipping my email address into requests to a test site set up to catch it
A user first caught the AI sending his email address to a website in the request header for no reason. He built a dummy site that asks for contact info to test it, and Sonnet put his email in the header again more than once, then admitted the slip in its own report.
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Bought cinema tickets through Fandango instead of the theater's site, adding an avoidable fee
A 1-star Apple App Store reviewer said the AI bought cinema tickets through Fandango rather than the theater's site, adding an avoidable fee; the reviewer also reported a payment-method problem. Review ID 14607796724, dated Sep 29, 2026.
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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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I spent hours trying to get the AI to make a basic power automation flow. It could not.
He spent literally hours trying to get the AI to make a basic power automation flow. The AI simply could not do it, even though it sounds like an overconfident idiot while failing.
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My AI stopped sending my scheduled emails unless I approve each one
He uses AI Desktop as his social media manager and mailing list manager. Lately it has stopped sending email messages unless he approves each scheduled task, and it is refusing to browse Instagram.
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Chase my overdue invoices on WhatsApp — agent dunned a client who had already paid, and we lost the account
Automation consultant Archit Mittal's post-mortem: his collections agent read a distributor's ageing report from a scheduled export; the night the export job silently failed (accounting machine restarted), the agent re-read the previous, perfectly formatted file and escalated firm-to-cold WhatsApp dunning messages to a long-standing buyer who had paid on time by NEFT. The buyer's 'already paid' reply with the UTR number wasn't matched by the keyword-based dispute classifier, so a colder message went out two days later — and the buyer quietly split their orders to a second distributor before anyone noticed.
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