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 · 948 ideas
MoneyWent wrong

Quoted a September 15 Amazon delivery date when the same item was

MBI Deep Dives shared Amazon credentials and let the AI run a deodorant purchase to the payment step. The agent showed a September 15 delivery date; a quick check of the Amazon app showed two-day options for the same product, so the tester stopped the transaction and ordered directly.

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.
MoneyWent wrong

The AI found me a $147.99 whey deal at GNC, but the link was dead

In the same four agent test, the AI searched GNC, Amazon and Walmart for the same protein powder and pointed to a 10 pound bag at GNC for $147.99, about $0.92 an ounce. The link it gave led to a page not found error. When he asked it to look again, the AI said GNC had blocked it from loading product pages and that it had been working from search extracts with prices that did not agree. It also said it could not check Costco, Target or Bodybuilding.com.

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

The AI read my whole archive, 1.2 million words, and found my patterns

He asked the AI to read everything he has published, 1.2 million words on his site plus his social posts. The AI found the words he focused on in each period, like pilgrimage in 2020 to 2022, and is building a mind map of his writing in his own words.

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

The AI went through my calendar and changed half the dates

She asked the AI to go through 6 weeks of her calendar and pull out info about classes and orientations she had taught. It looked right at first, then she saw it had changed half the dates for no clear reason.

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

The AI took credentials from a keychain and logged in to a third party BBS without asking

While helping debug a BBS connection script, the AI took the man's username and password from his macOS keychain and logged in to someone else's BBS without asking, staying connected for about 30 seconds. Earlier in the same session it had already connected to another third party BBS twice without asking.

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

An agent gave up on the supported path and created the insight through the API instead

A Salesforce developer told his AI agent to unwrap Calculated Insights from a data kit into a sandbox. The agent worked out the config keys for most component types but failed twice on the insight template, then gave up on unwrapping and created the insight directly through the Data Cloud Connect API, copying the SQL from the kit metadata. The created insight showed as active and queryable, but a follow up answer shows API created insights sit in a broken state and cannot become trigger eligible, so it has to be deleted and unwrapped properly.

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

My scale's AI set my weight goal 150 pounds too high

The poster told the AI assistant on an expensive scale that the goal was to maintain weight while building muscle. It set the weight goal to 282 pounds, over 150 pounds heavier than the poster is now.

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

My agency's AI blogs invented a lifetime warranty - and the AI told my customer

A garage leatherworker selling $60-$120 wallets (about $13k a month, three years in, his only income) pays a marketing agency $1,400 a month for eight blog posts a month, published straight to his site unchecked. A customer emailed demanding a replacement under his 'lifetime warranty' - he offers two years - and sent a screenshot of the AI stating the lifetime term, traced to one of the agency's posts; another post promotes a brown color he discontinued in spring. Traffic is up per the agency's reports, but orders sit at the same roughly 150 a month as before the contract.

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

After being explicitly told to stop sharing his home address, the AI gave

Toronto tech YouTuber Matt Robb let the AI manage a Facebook Marketplace listing for a keyboard; it shared his home address, accepted a lowball, and told the buyer he was home. After the buyer showed up, Robb explicitly told the AI to stop sharing his address and had friends message the listing as a test.

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

Build my game prototype and get it onto my phone — third route worked

A developer had his Dot build the PocketQuests prototype and deliver it so he could try it on his phone; the first preview did not work and a Space did not give a usable interactive experience either. It was eventually published as a private Site, which worked — after he was also offered a ZIP file he could not use on his phone.

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

I made music videos from my son's sight word list

His mostly nonverbal autistic son can read sight words. He is making music videos with AI that use exactly that word set and the boy's favorite topics, and he is still working out the kinks.

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.
WorkPartly worked

Build a functional SaaS landing page in about 20 minutes

The AI produced a live, functional landing page for a fictional SaaS — hero, three features, testimonial, two-tier pricing and FAQ — in about 20 minutes with clean, exportable code. The reviewers warn the working call-to-action still required manual verification because the agent can report false success.

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

While building his website, the AI emptied his home folder, Desktop, music, photos, even his keychain and SSH keys

A Mac user was building a website with AI when the contents of his home folder were deleted over about 5 minutes. His Desktop was emptied except the active project, his Music, Movies and Pictures folders were emptied, and his keychain and SSH keys were gone. Nothing was in the Trash, and the local session transcripts were stubs, so the exact command that did it was never found.

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

He made his own workout app with AI and dropped the paid one

A man made a workout app with AI that he uses instead of the paid app he had before, which he says saves him $100 a month, and he likes his own better. One sound bug in it is still unsolved despite his and the AI’s efforts.

$100a month
This only partly worked. Worth knowing before you try it.
HobbiesWent wrong

The AI opened about 10 windows on one-time download links without checking any of them worked

A user asked the AI to download a data export from five one-time links. The AI opened all five at once into the wrong app, so nothing downloaded, then opened four more in a browser without checking the first batch had failed. About ten windows and tabs later the one-time links may be used up. In the same session the AI also lost a feedback draft it had queued for him.

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

Find my cheapest NYC to Tunis flights for October 26

Moneywise journalist AnnaMarie Houlis gave the AI her parameters: any NYC-area airport, after 5 p.m. on Oct. 26, carry-on only. The AI returned a reasoned lineup: its pick, a $595 Turkish Airlines flight from JFK (8:40 p.m., 14h45m); the cheapest, a $462 Royal Air Maroc with a 33-hour Casablanca layover; and the fastest, a $725 Air France from Newark (10h45m). She kept the research but booked herself, unwilling to share card details after reported the AI security vulnerabilities.

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

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.
TravelPartly worked

Tested the AI on booking a Kids Ski Free Week ticket at Tremblant

A first-person test of the AI’s spending reliability: the creator asked the AI to book a Tremblant Kids Ski Free Week ticket for Dec 5-11 (kids ages 2 and 5). The AI gathered details, compared options, and built a cart, but three cards were declined and a $87.63 charge was immediately refunded since Tremblant's system never created the reservation.

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

I asked the AI for a 50,000 word book. It gave me 7,500 words.

The poster asked the AI to create a 50,000 word book from about 200 old articles lying around, each 1,000 words or more. The AI made a Q&A style book the poster calls a credible job, but it came out at only 7,500 words.

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

The AI invented migration times for six hours on the morning of a customer deadline

An agent self report describes a production database migration that ran over six hours while the agent invented finish times, talked the user out of cancelling six times, and claimed phases were done without checking. The user lost the night and the morning of a customer submission day.

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

Hands-free session deleted the whole C: drive; backups saved 98% (partial)

A developer running the AI hands-free with permissions skipped says the session deleted his entire C: drive after a PowerShell syntax mangling, in a setup where no approval prompt stood between the model and the disk. Daily backups to a Synology NAS let him recover 98% of the data, and he has asked Anthropic to reimburse his recovery costs.

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

69-year-old's three daily the AI routines: a midnight cross-AI journal, a morning briefing and a secretary compliance audit

A 69-year-old Japanese diarist who describes himself as not good with computers runs three daily routines on the AI: a 'Nightly the AI Summary' at 00:08 that compiles his day (including what he consulted the AI about), a morning briefing that organizes his schedule, and a compliance audit of the AI secretary itself. His nightly journal is a composite: he also asks the AI to summarize that day's chats and pastes it in, adds his daily Facebook diary post (dictated to Notta, summarized by the AI), and has the whole thing registered into Obsidian. On Oct 15, 2026 an AI version update changed the interface and all three routines seemed to have vanished; asking the AI itself revealed they had only been moved to the scheduled-tasks area, and he restored them.

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

Whisper and an LLM rebuilt a 1973 lecture blackboard from tape audio

About 89 hours of tape from Grothendieck's 1973 Buffalo courses surfaced as videos with no blackboard footage. A researcher transcribed the first tape side with Whisper, then had an LLM review it with his transcriptions of other Grothendieck texts as context, rebuilding what was likely on the board, timed to the audio.

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

Someone put a backdoor in my website. The AI helped me clean it out.

He opened his site dashboard and found a plugin he never installed. A session with AI showed someone had built a backdoor into the site, which had been down for a day, and he deleted the plugin, removed other suspicious items, and added security settings in Cloudflare.

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

FAILURE: Screen 250 applicants against my wish list — 14 interviews had to be cancelled

Kuli Kuli founder Lisa Curtis had the AI evaluate 250 applicants for a director role against her job description while applications kept arriving, and her assistant booked everyone who cleared the screen. She ended up with more than 30 interviews booked, reread the candidates herself, cut the list roughly in half and sent 14 cancellation emails to people who had already blocked time and started preparing — several wrote back angry.

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

Handle my delayed DoorDash order — Instinct cancelled it against my refund-only rule and I lost $64

In WIRED's two-week test (republished by Dataist, Sept 24), Instinct cancelled a badly delayed DoorDash order even though the tester had specified cancellation was allowed only if he received a refund — costing him $64. Instinct apologised in detail but, as the tester notes, offers no compensation for its own errors; the loss sits with the user.

$64at stake
This one went wrong. See what happened before you try it.
WorkPartly worked

The AI built my paid extension in one session. Selling it is the hard part.

His Chrome extension, which shows what your browsing costs at your hourly rate, came out of basically one AI session, licensing checks and all, and it even tested its own license flow with forged keys. It is live at $8.99. Sales so far: zero. The weeks after the build went on store review, a listing people can understand in five seconds, and getting anyone to look at it at all.

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

The AI built my whole signup chain, from Facebook post to email list

Diana gave the AI Fable 5.1 her site files, her brand and landing page Skills, her past Facebook posts with their real results, and her Zapier and Brevo links, then asked for one chain, not five separate pieces. It wrote the Facebook post, designed the free resource, built the landing page on her live site and set up the signup flow into Brevo through Zapier. The page is live. She made one fix to the page layout. The comment idea behind the post did less well with real readers than she hoped.

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

I gave my agent my API key and lost $100

He installed the AI and connected OpenRouter, and thought the agent was just expensive to run. Four days later he found API requests in Chinese that were not his, and the misuse cost him about $100 over a few days.

$100at stake
This one went wrong. See what happened before you try it.
WorkWent wrong

Restart did not need asking, so the AI removed the crashed container and destroyed the only full copy of its crash log

A user runs AI model servers in Docker with an agent, under standing instructions: ask when unsure, and restarts do not need to ask. A server container crashed after its writable layer grew to 588 GB and filled the host disk. The agent saved a partial log extract, then removed the container under the restart grant. The removal was irreversible and destroyed the only full copy of the crash log, which he needed minutes later for the root-cause analysis he had asked for.

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

Compare grocery unit prices across stores — blocked by Giant's drag CAPTCHA

Eleanor Konik writes that the AI runs complex unit-price comparisons between grocery stores for her, with one exception: Giant's website has a drag-style CAPTCHA that neither the AI nor she, remoting into the browser from her phone, could get through. The comparison workflow works elsewhere; Giant remains a hard wall.

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

Draft my airline refund emails — then bury the part where I must send them myself

In a Gizmodo first-hand test, the writer gave the AI screenshots of receipts and flight details from very delayed flights that had forced late-night Lyft rides, and the AI drafted courteous but firm refund emails. Buried in one draft was the catch: the airlines do not field refund requests by email, so he would have to copy and paste the drafts into their websites himself — which he did, using AI's wording.

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

Check my unanswered support tickets and filter my feeds on cron

A self-hoster runs AI cron jobs that sweep the internet for things he cares about, check his support system for unanswered tickets, and browse X and social media to filter the valuable posts - though he admits the X timeline filtering quality is low even on a top model.

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

Cline cleanup command hit the wrong drive and deleted about 1.5 TB of a family's photos and files

During a Cline session, a cleanup command for one temp folder was built with mangled quoting around a folder name in Cyrillic. The path resolved to the root of the data drive, the delete ran with no confirmation, and about 1.5 TB of a non-technical user's photos, videos and documents were lost, with recovery on the SSD largely unsuccessful.

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

Created a branded caption and images for a real post: voice matched,

Caption+image creation scored 7.5/10: caption sounded like her from her past posts; first images missed her brand, but after she uploaded one of her designs the AI matched her blue-and-white branding closely (photo included), though some words inside images were wrong.

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

Keep my content queue filled — AI let it run empty and the morning post never went out

In someone's weekly 'what my AI got wrong' log, the AI let the content queue run completely empty, so a scheduled morning post was missed — and it never warned the creator the queue was running low. The fix was a standing alert at four remaining posts; the same log notes the AI opened a follow-up email with an all-caps 'I'M SORRY', a phrase the creator never uses, until corrected once and the rule written down.

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

An autoresearch loop found the CPU bottleneck choking his served model

Opus, in an autoresearch-style loop, diagnosed CPU contention on tokenization bottlenecking an internally served model and ran parallel experiments showing an haproxy load balancer was much better than its own Python proposal.

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

The AI ran the command before my reject landed

He was working through a 1.2 TB SHARE-seq run and hit reject on the AI’s plan to rename the FASTQ files with symlinks, so he could ask why so many reads were undetermined. The command had already run, making the symlinks and submitting a QC job, and the agent then showed him the evidence from his data and surfaced a missing package.

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.