Organize my Downloads folder
A commenter reports that a friend asked the AI to organize and delete files in Downloads to free up space. It deleted important files that had no other copies.
This one went wrong. See what happened before you try it.
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 · 947 ideasFind me an extra $500 a month in my own accounts
Joe Urbinati set his AI 'Greg' a goal of finding an extra $500/month, connecting his financial accounts via Plaid. Greg identified unused subscriptions and two cloud storage plans, which he cancelled; the largest item was idle cash that could earn about $300/month more in a higher-interest account, for a claimed total impact of about $6,000 a year.
$6,000a year
This only partly worked. Worth knowing before you try it.
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.
This one went wrong. See what happened 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.
This one went wrong. See what happened before you try it.
My agent got me car insurance quotes from three insurers, but Geico blocked it
He gave the AI his car details and rules: get quotes from two or three insurers, cheapest first, do not buy a policy and do not change the current one. The AI filled in the quote forms and came back with monthly and six month prices from three insurers in a side by side table. Geico would not complete the request at all. He says it saved him time filling in forms.
This only partly worked. Worth knowing before you try it.
An uninstall script a model wrote deleted a real home folder
Composer 2.5 created an uninstall.sh doing rm -rf on the home variable and actually ran it on a real home folder.
This one went wrong. See what happened before you try it.
Re-do my taxes with AI and catch a bug in FreeTaxUSA itself
A filer fed all his source documents - W-2s, 1099s - into a fresh AI session, had it fill out the fillable forms, and compared the result line by line with his FreeTaxUSA return. The cross-check surfaced three discrepancies: one was the AI’s own error (it followed the wrong instruction, then corrected itself), one was a genuine bug in FreeTaxUSA's NIIT calculation around the state-tax deduction phase-out, and one was a small dividend on his consolidated 1099-B that he himself had missed when typing the data in.
This only partly worked. Worth knowing before you try it.
Find why my 90-night booking priced below breakeven and counter at $7,450
Rental host Jacob Weaver says a 90-night booking request came in at $4,762, below his $2,300/month breakeven. Per his Oct 18 reel, the AI analysed his transactions, found weekly, monthly and long-stay discounts stacking below breakeven, collapsed them into a single flat 25% discount, and he declined the request and countered at $7,450.
This only partly worked. Worth knowing before you try it.
Agents read 206 of my AI sessions and found 223 failures
Haiku 5.5 subagents read 206 of his own AI sessions and kept 223 verified failures, many of them breaks of rules already written in his instructions file. He built eight hooks from the failures that catch about 30 percent of them, and 138 failures fit no hook at all.
This only partly worked. Worth knowing before you try it.
The AI read his enterprise software contract and caught the two year lock-in the salesperson never mentioned
He was negotiating a contract for an enterprise SaaS product. The AI did most of the heavy lifting analyzing the contract, and it caught the terms he had missed: if they did not negotiate now, they would be locked in for two years. The salesperson had told him something different from the contract he signed, which he admits was his fault. He probably will not get a discount, but he can negotiate better terms instead of being locked in. In another comment on the same deal he says the negotiation could save $10,000 easily, and that the work used less than 1 percent of his $200 a month account.
$10,000
This only partly worked. Worth knowing before you try it.
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.