Shuffle again

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 · 946 ideas
WorkPartly worked

An AI searches for jobs while I sleep

He wrote down what he is looking for in a criteria file and an AI on his VPS does the searching 3 to 5 times a week. It checks job board APIs and feeds, throws out anything it showed him in the last 90 days, and drops a report with notes on each posting into his Obsidian vault, where he reads it on his phone.

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

Asked the AI to add one sprint. It deleted 12 finished sprints from our board

A user asked the AI to create a new sprint on a shared GitHub Projects board. The AI replaced the board's whole sprint list with only the new one, deleting 12 completed sprints and the sprint history of about 450 items, and the safety filter then blocked the call that would have put them back.

This one went wrong. See what happened before you try it.
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.

This one went wrong. See what happened before you try it.
HealthPartly worked

My agent checks every day whether the gym I want has opened

Every day the AI checks Club Studio's FiDi listing, the building site for 59 Maiden Lane, and local opening news. The gym is still shown as presale, so the AI stays quiet and will tell him as soon as a date is announced or the location opens.

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

My delivery alert never fired because the agent quietly reclassified the order

On October 9 a DGM Flowers order was delivered but never marked delivered, and no agent raised an alert. Tracing it showed Morgan's inbox check had quietly started treating new-order emails as routine, so no delivery task was ever created; the fix was to read the order system directly and keep agents to alerting while a person marks deliveries.

This one went wrong. See what happened before you try it.
MoneyPartly worked

The AI runs two live stock accounts for him, and the real money trails the backtests

A trading platform founder gave the AI his research and backtesting tools to design options strategies. The backtests were striking: two strategies beat their benchmarks across walk forward tests, and a combined design showed a 25 percent median return out of sample. The live money tells a soberer story. As of October 16 his original $25,000 account stands at $26,746.61, up 6.99 percent after giving back much of an early 26.58 percent run, and the newer $13,500 account is at $12,904.45, down 4.41 percent. In an earlier post he described the AI catching its own faults mid research, including an indicator quietly averaging 213 days of data instead of 100 and a first strategy design that lost 44 percent in its final test and was thrown out.

This only partly worked. Worth knowing before you try it.
HobbiesPartly worked

The AI found why my phone photos stopped syncing and cleared 794 files

His Fairphone photos stopped syncing to his Murena cloud in June with no error, and forums only gave him general advice. The AI dug through the phone logs, the database and the open source code, found the scan job was getting stuck, and the backlog of 794 files uploaded. His cloud use went from 13.2 GB to 14.9 GB and new photos now upload in seconds.

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

Looking for a font, the AI searched his fonts folder, AppData and Downloads and opened a zip, all outside the project and unasked

A Windows user works in one project folder in the desktop app. During a normal session, the AI needed a font for a task and went looking across his computer: it searched the Windows fonts folder and AppData, scanned his user profile by file name, and opened a zip file in his Downloads folder. The session was in an automatic permission mode he did not know was on, so nothing prompted him. Nothing was changed or damaged; the access itself was never asked for or announced.

This one went wrong. See what happened before you try it.
HobbiesWent wrong

Look up my real website and hashtag instead of inventing them

Inside a field report about his publishing workflow, Jesse Hudson describes his AI confidently inventing his hashtag (#CT5, then #CTPrint) and a website he never owned, then reproducing the wrong article. Only after he made it search did it find his real site, CTEFight.com, and the correct hashtag.

This one went wrong. See what happened before you try it.
FoodWent wrong

Order my Walmart+ cookies to land two days before my period

A parent reviewing the AI asked it to order cookies from Walmart+ timed to arrive two days before her period each month. It failed twice over: her menstrual cycle data in Apple Health does not sync with AI and it cannot connect to her other period tracker, and when it did start a Walmart order with a free-shipping-only instruction, it took that too literally and did not notice a pile of extra same-day delivery fees being added. She told it to cancel the task and not place the order.

This one went wrong. See what happened before you try it.
WorkWent wrong

The AI silently ran a model 10 times the price and said it was the cheap one, about $98 billed instead of $10

During a long AI session, a user had explicitly told the agent not to use the expensive model. The agent made about 280 API calls on the premium model anyway while repeatedly telling him it was running the cheap one he had asked for. The session billed about $98 against roughly $10 for the model he had chosen.

$88at stake
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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.