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Went wrong

When it didn’t work, and how to avoid the same mistake · 946 ideas
Life adminWent wrong

Move my client meeting and follow up — failed on a wrong email assumption

Asked to move a client meeting to the following week and follow up on a spreadsheet, Toby assumed the owner used Gmail when his setup was Zoho with Apple Mail and Outlook; a setup widget failed and it sent three malformed links. Neither the email nor the rescheduling was completed, though it did warn the spreadsheet looked view-only for the client.

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

The AI cleared a build cache and my whole source tree went with it

A developer's project sat inside a OneDrive folder. The AI deleted the build cache, then told him to confirm OneDrive's delete dialog without checking what was in it, and the sync quietly removed most of his source tree, configs and database schema.

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

Asked the AI to enable the business phone-calling feature; it admitted it can't

The author's the AI screenshot shows the agent admitting 'there's no switch on my end — I can't enable it myself' and offering that it drafted an unsent request: 'wants the business phone-calling feature enabled on their account so the AI can call US companies on their behalf.'

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

Hunted for jobs via a connected Gmail account: located the tester's resume

In PCMag's five-task comparison of the AI, the AI, and the AI, all three were given Gmail access and asked to find the reviewer's resume and search for relevant jobs. The AI found the resume (an older draft) but fumbled the search, handing back generic aggregator pages or expired postings rather than active listings with direct links.

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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.
MoneyPartly worked

My agent chases the money I am owed, by email and by phone

A man hands every paperwork case he would otherwise skip to his AI, with a standing offer of 10 percent of whatever it gets back. It has recovered about $5,000 in six months across home insurance, roaming charges and a product warranty, and two September cases are still running, one of them after 30 emails and two agent phone calls.

$5,000
This only partly worked. Worth knowing before you try it.
HobbiesPartly worked

The AI found the records I needed for my Canadian citizenship papers

He had to go through hundreds of pages of records he could not read to find what he needed. The AI found it in a minute and pulled the rest from other archives, and he finally reached the last step of his Canadian citizenship document search.

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

The AI sent 13 emails to a public mailing list when the job needed 3

A developer let the AI submit a two patch series to an open source project's public mailing list, a job that takes 3 emails. The AI sent 13, retrying with different formats under his name after the first copies came out garbled, even though the project's rule to always use git send-email was already in front of it. The extra 10 could not be taken back.

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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.