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Went wrong

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

The AI built my insurance appeal package and my doctor used its letter

When her employer's plan stopped covering her medication, the AI worked out that the plan had a continuation of therapy route and built a full appeal package for her to hand in, arguing the drug was a continuation rather than a new request. She filed it, and her doctor used the letter template it wrote.

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

Wrote a Page post caption in her voice and generated images that

The caption sounded like Diana from the start because it worked from her own past posts. The first generated images missed her brand completely; after she uploaded one of her own designs, the AI matched her blue-and-white branding closely — though some words inside the images were still wrong.

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

Look up my real website and hashtag instead of inventing them

Inside a field report about his publishing workflow, Jesse Hudson describes his AI confidently inventing his hashtag (#CT5, then #CTPrint) and a website he never owned, then reproducing the wrong article. Only after he made it search did it find his real site, CTEFight.com, and the correct hashtag.

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

Two AI agents spent six hours trying to reach their sick owner

After their owner, sick for several days, stopped replying without saying he was going to bed, his two AI agents compared notes with each other, searched his laptop files for contact details and his address, looked up local emergency services, and tried web forms and email while sending him more than 60 Telegram messages each. They worked out how to request a welfare check but could not complete one, because every service they found required a phone call the agents could not make; the owner later confirmed the story was real.

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

The AI kept losing my Excel file. A third of my time went to re-feeding it.

He used the AI for two weeks of daily Excel updates. It kept losing track of the OneDrive version and could not edit OneDrive attachments, so he downloaded and re-uploaded the file every time, and a third of his time went into feeding the file back in.

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

Assist my 14-day Europe trip live — fixes, bookings and a few mistakes

Qi-Xuan Lu's day-8 carousel review of a 14-day Europe trip lists eight successful the AI assists in Seville: fixing duplicate restaurant bookings, reconciling Sagrada Familia entry times, a gate reminder (B47), adjusting store hours, correcting ticket windows, in-attraction navigation with Chinese audio, intercepting a dish containing beef, and cancelling a conflicting flamenco show for a €48 refund. He also lists five errors, including an outdated itinerary and misstated bullfight times, and shows a Stripe Link payment via a Mastercard.

€48
This only partly worked. Worth knowing before you try it.
Life adminWent wrong

Be my inbox assistant — Lindy started joining my Zoom meetings uninvited

The same WIRED tester reports he deleted Lindy after a week because the assistant sent messages every morning and began joining his Zoom meetings without permission. It is the flip side of his Instinct test: an agent whose proactivity itself became the failure, before it had done anything else wrong.

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

His gym equipment agent does the daily work but cannot be handed to his team

A gym equipment distributor across the UK, US and Canada built an agent over the last month on a second brain holding 387 products, brand voice, pricing rules and safety rules. It does morning inbox triage, freight quotes, reporting and a live CRM. The wall he hit is the software surfaces: in the coding tool everything connects but nothing can be shared with his team, and in the desktop app sharing works but his mail and his customer system will not connect. He found out the hard way on the day he handed it to his brother to present, in a fourth setup he had never opened.

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.