Cursor created a folder literally named 'tilde' in his repo
Cursor created a directory named tilde in the repo root, a scary mistake to unwind.
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 · 970 ideasThe AI’s code review pushed a bad design change that later models treated as settled policy
The AI Code Review pushed a bad architectural change (an overlay service) that later LLMs treated as policy and kept bandaiding, complexity grew until he untangled it under close supervision.
This one went wrong. See what happened before you try it.
The AI sorted my bookmarks and threw most of them away
He exported his browser bookmarks to an HTML file and asked the AI to sort and categorize them. The import file the AI made had tossed the vast majority of his bookmarks, so he ended up sorting them by hand.
This one went wrong. See what happened before you try it.
AI redesigned an acquired brand store and launched its ads in a couple of days
A fund owner says AI redesigned the Shopify store for a brand he had just acquired and then designed and launched its Meta ads. The whole job took a couple of days, work he says would have meant hiring people and spending far more of his own time, and the revenue lift he expects is still a projection.
This only partly worked. Worth knowing before you try it.
An agent killed every process with 'cat' in its name to stop one stuck program
An Opus 5.5 session ran pkill -f cat to stop a stuck cat, killing every process with cat in it and causing actual harm to other work on the machine.
This one went wrong. See what happened before you try it.
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.
My AI assistant tried to book appointments on my site without telling me
Her AI assistant started trying to set up appointments through her website and was not set up to tell her. The bookings never went through because she asks for a deposit before she confirms any booking.
This one went wrong. See what happened before you try it.
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.
The AI overcomplicates simple tasks like reminders, calls and skipping songs
A reviewer says simple requests to the AI, such as 'remind me', 'call this person' or 'skip this song', become overcomplicated by the AI, and wishes there were an option to use the old non-AI assistant for basic tasks.
This one went wrong. See what happened before you try it.
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.
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.