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Went wrong

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

Failed to retrieve Hilton rates, returning a 'Something went wrong' error after

Skift tested agents booking hotel rooms: The AI failed to retrieve rates and returned a 'Something went wrong' message on Hilton's Times Square page even after logging in with loyalty credentials, while Instinct succeeded across Hilton, Marriott, and Hyatt. Hilton says it isn't blocking agents — the failures read as technical.

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

Re-do my taxes with AI and catch a bug in FreeTaxUSA itself

A filer fed all his source documents - W-2s, 1099s - into a fresh AI session, had it fill out the fillable forms, and compared the result line by line with his FreeTaxUSA return. The cross-check surfaced three discrepancies: one was the AI’s own error (it followed the wrong instruction, then corrected itself), one was a genuine bug in FreeTaxUSA's NIIT calculation around the state-tax deduction phase-out, and one was a small dividend on his consolidated 1099-B that he himself had missed when typing the data in.

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

The AI refused a read-only network assessment tool as a cyber risk

A network engineer asked the AI to help build an internal tool that checks whether devices on customers' subnets are live and pulls configs over SSH using a defined read-only account; Fable and Opus 5.5 refused under cyber guardrails. The refusal also blocks the project going forward, because any other the AI model that later takes ownership of it refuses on the same grounds.

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

Edit my 90-minute tennis match down to just the points

Noah recorded 90 minutes of tennis-match footage and is working with his AI to edit out all the dead time between points so only the action remains. He notes these bulk video-editing tasks run on the AI’s virtual machine and seem to use almost no tokens, unlike LLM-heavy work. The edit was still in progress in the video.

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

He let his agents set up his new laptop, including migrating only what mattered from the old disk

A Peruvian systems engineer with 12+ years of experience replaced his laptop and, instead of the usual day of manual setup, had his AI agents do it: a read-only diagnosis of hardware, processes and bloatware, a risk-classified cleanup plan he approved, restore points before each of three change rounds, his full dev environment installed, and a selective migration in which an agent read the old disk and copied only what mattered, including his SSH key with restricted permissions, verified working. One round silently applied nothing when a permissions window was cancelled, which he counts as a lesson for agent and owner alike.

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

Send my resume to jobs for me — service sent 150 applications full of invented facts about me

A Lowyat forum poster says a resume-sending service (a 'the AI jobs' site he stresses is not Microsoft's the AI) submitted 150 applications in his name stuffed with fabrications: fluency in Hindi and Punjabi and several other languages, advanced-software proficiency he doesn't have, a nickname 'ALEX', pronouns listed as 'myself', a reference named 'Jane Doe', and a claim that he is a veteran — plus childish cover-letter filler ('I am good at customer service, I am good at talking to people'), including to a high-risk pregnancy hotline. He calls the result absolutely humiliating.

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

An automatic coding pipeline merged 67 pull requests in two weeks, then he shut it down

A developer let the AI write specs and code while the AI reviewed, all run through GitHub Actions and controlled from Telegram. Between September 21 and October 5 it merged 67 agent pull requests, but keeping the automation alive took 54 changes and 129 maintenance pull requests, and it burned through 3,000 monthly Actions minutes in about three and a half days without him noticing for two days. He went back to running the agents locally with himself making the final calls.

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.