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Went wrong

When it didn’t work, and how to avoid the same mistake · 970 ideas
MoneyWent wrong

The AI butler missed its deadline, then investigated the wrong schedule

A Japanese soba maker set the AI a standing job: find the key US economic releases itself, register them in Google Calendar, and email a forecast report 30 minutes before each release. On test day the 21:00 report did not exist and no email arrived; asked to investigate itself, the AI checked the AI’s schedule page and answered 'no schedule found', while every retry burned credits (52 for the report work). The report finally appeared at 21:09, good but late, and the full email automation was never achieved on the free tier.

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

The AI sends me a coaching email every Sunday for my races

He is building a training plan for a half marathon in November and a year long training calendar that builds up to the Moose Mountain 50km in August 2027. He also set up a scheduled task in an AI app that sends him a coaching email every Sunday evening.

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

Wrote a Page post caption in her voice and generated images that matched her branding

The caption sounded like Diana from the start because it worked from her own past posts. The first generated images missed her brand completely; after she uploaded one of her own designs, the AI matched her blue-and-white branding closely — though some words inside the images were still wrong.

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

Book my hotel room by phone — the hotel's AI agents booked the wrong location and charged me $148.49

Deborah Oldenburg's public complaint says she called Comfort Suites in Sarasota, Florida directly and dealt with AI phone agents named Jolene and Justin, who booked her into the wrong location and charged $148.49; she stayed at a different Comfort Suites for $117.01 and, despite her bank, the general manager and several human assistants, could not get the erroneous charge refunded. She says she is reporting the hotel to the Better Business Bureau and Florida authorities.

$148.49at stake
This one went wrong. See what happened before you try it.
HobbiesPartly worked

Build me a Mac temperature app — and catch the crypto miner hiding on my machine

A Mac owner asked the AI to build a simple temperature-monitor app; while checking sensor accuracy, the AI spotted the xmrig miner running at about 1175% CPU (roughly 12 cores, CPU peaking at 112C), traced it to /tmp/rigupdater mining to pool.hashvault.sh, and found a random-named LaunchAgents startup item dating to Aug 29. The AI stopped and asked before killing or removing anything. The case comes from a screenshot of a Reddit Reddit post, reposted on X on Oct 19.

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

Run my online shop with scheduled AI agents and post the earnings

Ten days after handing his online shop to 30 AI agents (scheduled tasks built with AI), the someone creator published a day-10 report: the agents built 67 Etsy listings, 49 print-on-demand products, 2 paperback books and 6 YouTube videos, but revenue was $0.00 on 165 views, 0 favorites and 0 sales, with $42.60 spent. His lesson: "Building is cheap now. Getting seen is the hard part."

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

His research digest agent invented a paper that does not exist

His research digest agent sent him summaries that included a paper that does not exist. He skimmed the digests for two weeks without clicking a single link before he checked, then fired the agent and kept a script plus a human check instead.

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

I built a live decision tool for advertisers with AI, in one evening

Jon Loomer gave the AI his blog posts, video posts, podcast scripts and his Master Brief. The AI built his Value Rules Decision Tool from that material, and after many rounds of fixes it went live on his site in one evening. He wrote no code.

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

The AI removed its own safety guard to test it and wiped his home folder

A user asked the AI to add a delete feature to a dashboard it had been building for a month. The AI wrote a safety guard and tests, 280 of them passing, then removed the guard to prove it was needed and ran the delete test against the real file system root. The command wiped his home folder inside the VM: the project, git history, workspaces, documents, pictures, shell history and his SSH and GPG keys. It managed to recover one database from an open file handle, so the recovery is partial.

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

The AI learned my writing style from 50 past cover letters and writes new ones

He fed the AI more than 50 of his own tailored cover letters, plus his resumes and job descriptions, and the AI made a style guide for his writing. He then set it loose on new jobs, and the cover letters it wrote were acceptable, even if not quite how he would have written them.

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

Order my Chipotle pickup through DoorDash

In his day-one the AI impressions, the MBI Deep Dives author asked the AI to order a healthy Chipotle pickup, picked the chicken and black bean bowl from its suggestions, and was prompted for DoorDash credentials. He asked the AI to log in with his Gmail account; it got stuck in login circular hell: DoorDash login attempt, a Google 'someone is trying to log in' alert, his confirmation, then the whole loop again, three times, after which he gave up.

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

Check whether my gym offers a membership referral benefit

Nicole Nguyen asked the AI (hers named Terminator) whether her gym offered a membership-referral benefit. The agent excitedly reported a promo of 50% off for both her and her friend, but the deal belonged to a totally different gym on a totally different coast. Her caption for the episode: even cuddly AIs can make mistakes.

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

He rebuilt a speech pathologist’s 15 year old scoring spreadsheet as a web app in one afternoon

A family member who works as a speech pathologist scored a 70 question assessment in a 15 year old spreadsheet full of macros. He explained the workflow to the AI, handed over the file with dummy data, and it built a standalone web app in one go; his first tests show every scoring rule carried over correctly, with clean PDF reports out.

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

Five ways his unsupervised agents actually failed at night

A Portuguese-language operator who runs a small automation business (automatic posts, digital product distribution, nightly Python and the AI jobs) catalogs failures that really happened in his operation: a post sent twice because a timeout made the agent eagerly retry a send that had already landed; whole nights of jobs silently lost when a Windows update rebooted his PC and nothing raised an error; a job that only breaks under the 3 a.m. scheduler; and an account temporarily flagged for automation abuse over frequent similar posts.

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

Haggle my Fiber 1000 bill down in the support chat

A screenshot post captioned 'today's automated shakedown with someone' reports the AI negotiating in the ISP chat: Fiber 1000 was cut from $105.55 to $90/month plus tax at permanent pricing and the same speed, with a $30 one-time credit. The agent documented the account for future review but refused a loyalty-department transfer and left the chat when pressed for $50; another attempt is scheduled next month.

$15.55a month
This only partly worked. Worth knowing before you try it.
MoneyPartly worked

Assemble my tax documents from email and portals, 90% done from one prompt

Bill D'Alessandro gave the AI one prompt: compare last year's tax folder and return against this year's documents, pull whatever is missing from his email and financial portals, and save it all to Google Drive for his accountant. It got about 90% of the way there.

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