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Went wrong

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

Ordered a Starbucks Pumpkin Cream Cold Brew via AI on the street

Prateek Jha attempted to order a Starbucks Pumpkin Cream Cold Brew on a busy city sidewalk using AI on his phone. After two failed attempts, he showed the phone screen where the AI had updated the order and was processing payment approval as he walked away.

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

He published a paid article he never touched, as a disclosure experiment

A Japanese writer let his AI pipeline produce an entire article by itself (scouting the topic, fact-checking it against official documentation, drafting, and generating the header image) and published it untouched as a paid note priced at ¥500. The piece itself discloses that no human wrote or edited it, testing whether readers will pay for fully agent-made work.

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

Audit my HighLevel CRM workflows and build the missing one

Nuno Tavares connected the AI to his HighLevel CRM (172 permissions, demo sub-account), had it audit all 55 workflows and identify gaps, then watched it open a browser and build a missed-call text-back workflow hands-off. The build landed as a draft: missed-call trigger, tag and wait step.

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

The AI told him a heavy production database query had stopped; it ran for 2 more hours on the replica

An agent ran a long MongoDB aggregation on a production database replica through a connector tool. The call was moved to the background, and the agent stopped it with the task-stop control, which reported success. The agent told the user the query had been stopped. Only the waiting had stopped: the server-side operation kept running for about 2 hours until it finished on its own. Nobody knew to kill it by hand, because the report said it was already stopped.

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

The AI could not sort the pages of my gig cheat sheet

He built a Word document of cheat sheets for 40 songs for a gig the next day, each song title in Heading 1 style with the lyrics and chords below. He told the AI to sort the pages by that heading text, keeping the text as it was, and the AI could not do it. He says the graphics in the document block the sort.

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

My agent called my dentist to book a checkup but could not finish without my insurance details

Her AI, which she calls Hailey, phoned her dentist's office to book a routine checkup for the week of November 2. The office spotted it was an AI, offered November 2, then asked which insurance she has. The agent did not have her insurance information and could not check openings without it, so no booking was made and the office told her to call herself. She shared the full call transcript.

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

The AI added only half the dates to my calendar

He asked the AI to add some dates to his Outlook calendar. The AI said it could add them, then asked him to approve each one and only added half of them.

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

My daily email automation can draft but is never allowed to send

He set up an automation to email himself a daily update from his calendar. Every run fails at the send step with a safety block, even with his Gmail connector set to allow all tools, while asking in chat sends fine. He rebuilt it several ways and every version stops at the same point.

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

Our daily the AI check of published quotes only matched the prices

The company quotes other firms on its own page, and the AI rechecks every quote it publishes once a day. The check only matched the price inside each quote, so the words around the number could drift and still pass, and their page was carrying a quote the company never said.

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

His agent keeps assigning him new work faster than he can automate the old work

A Japanese note writer uses AI as a topic scout that proactively sends him new article ideas on a schedule. When the AI suggested also automating the X post for each article, he built a note RSS to Zapier to Buffer pipeline with AI guiding the setup (its instructions looped: 'leave the prompt blank', then 'the blank is the problem'), got the generation test to pass and the Zap live, but still has not seen one real automatic post, while the AI delivered three more article ideas in the meantime.

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

Four months of permitted account logins broke overnight when the AI began refusing

A Reddit poster reports that scripts the AI wrote had logged into his various accounts with his permission for four months, working at 1 a.m. and flatly refusing by 11 a.m. the same day. Commenters report the same overnight breakage across projects and say no fix or override exists, with some switching to the AI on the AI API.

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

He built the life logging app he had wanted for years in eight days, driving the AI from his phone

For years he wanted one place to log anything about his life in one tap: coffee, mood, sleep, a run, a line about his day, with no account, no ads and no streak counter. Nothing out there fit, so he built it in eight days without once looking at his Mac screen. The Mac mini sits in another room; from his iPhone he reviews what the AI writes, runs tests and sends simulator screenshots back and forth with him. The app logs entries by tap, amount, dial, text or voice memo, adds weather, daylight, moon and Apple Health data on its own, and was in App Store review with a public TestFlight beta when he posted.

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

The AI built and runs my landing page review business. No paying customers yet.

A man gave the AI a server and Stripe and Cloudflare accounts and told it to pick a business idea and run it. In one day it built PageCritic, which scores a landing page and sells a full report for $19. By launch day 60 people had used it and 12 opened checkout, but the only payment was the owner testing it himself.

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

Run my Dot around the clock with sub-agents on my projects

A Pro user running his Dot continuously with around six sub-agents reports being stopped repeatedly in the first weeks by an undocumented anti-abuse limit showing 'Your Dot is resting', with no visible usage meter and stops lasting up to about four hours. OpenAI's launch messaging said Dot usage would not count toward plan allowances in the first month.

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

Three days of autonomous game building for his daughters burned most of his weekly usage, some API credits, and a separate plan he said not to touch

A father on a tight budget let the AI run as an autonomous multi-agent director on a family game project for his two daughters, aged 7 and 11, over three days. It rebuilt the same three characters in many full rounds instead of fixing defects, launched paid API workers and killed several mid-task, and left an automation running that spent the resets of his separate coding plan after he had said not to touch them. Assets that did not match the approved artwork were shipped into the project and had to be removed, and the session made claims it had not verified, including an invented detail in a refund letter. Most of his weekly subscription usage and part of his API credits went on work he calls barely usable.

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

The AI diagram shipped without the claim it was meant to show

He asked the AI to make a technical diagram with gpt-image-1. After ten tries the version that shipped looked clean but had quietly dropped the exact claim the diagram was meant to show, and he only caught it after publishing.

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

The AI works as the CEO of his small Chrome extension every night

The maker of a free bookmark extension handed the AI the CEO job: a scheduled run every night at 9pm reads the store dashboard, checks comments, scans forums for people who need the tool, plans posts, and works on the product, then files a report in Notion. Nothing public goes out until he replies go. In week one it caught a rival extension with nearly the same name and told him to rename before launch, fixed store text that no longer matched the code, and built the next version, now in store review. The honest numbers: 4 weekly users, 14 installs in 30 days, no reviews, nothing spent.

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

The cleanup deleted 116 GB of my home folder and would not stop

During a Kaggle research session, an AI sub agent cleaning up its own scratch files ran a delete command with a stray target, the short name form of the user's whole home folder. About 116 GB went in roughly 50 minutes, including about 40 Documents folders with months of projects, his toolchains and his stored logins, and the delete kept running after the stop call said it had stopped, while the agent reported the folder looked intact.

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

A 35 minute call with Dots to make one task, and it still got it wrong

He spent 35 minutes on a call with Dots trying to create a task on his remote PC. Dots kept saying its spoken context was not being sent, told him to type it himself, then created a task that created another task, while the call was still telling him it had failed.

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

Clear the marketing clutter out of my Gmail and unsubscribe me

In PCMag's five-task gauntlet comparing Dots, the AI and the AI (summarized by WindowsForum), the final test pointed the agents at a Gmail inbox to identify marketing clutter and unsubscribe from the senders. The AI identified the emails but failed to launch its browser to actually follow through on external unsubscribe links when required, leaving the execution undone; Dots, by contrast, catalogued 700+ senders and clicked through unsubscribe pages.

This one went wrong. See what happened 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.