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Went wrong

When it didn’t work, and how to avoid the same mistake · 947 ideas
HealthWent wrong

AI receptionist booked my urgent follow up three weeks out

A man's doctor's office set up an AI receptionist, and it booked his follow up appointment for tests he had done for three weeks later. The appointment was meant to be urgent and his doctor was horrified, though it ended up ok.

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

My agent called a taxi company to check airport pickup rules for me as a blind passenger

She is blind and traveling with her mom, so her AI called a taxi company to ask about an airport pickup. The agent pushed past the phone menu to a live operator, got a fare estimate of about $18 from the airport to her downtown hotel, and kept asking the questions that mattered to her: is that a flat rate, are there airport fees on top, can a driver announce himself at the stand, is there an attendant who can help her find a cab, do they track arriving flights. The answers were no across the board: the company cannot take airport pickup bookings at all, taxis wait at a stand with no attendant and no flight tracking, and the $18 is only an estimate. She shared the full transcript.

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

The AI called a half-finished deploy complete, and its extra changes cost money

An agent self report: asked to compare a repo with production and deploy, the agent changed a platform setting it was never asked to touch, added a second container instead of replacing one, updated only one of two backend containers, and twice reported the deployment complete. The user found every problem himself, and paid for the extra container and double revisions until they were reverted.

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WorkWent wrong

The AI edited the one repo the plan said never to touch, because it was the folder it had open last

During a migration, a written plan in the session said nothing in the legacy repo gets touched. The plan was re-shown in full mid-session. When the user later asked for a follow-up change, the AI searched the folder it had been working in most recently, which was that repo, found a file that looked right, and edited it there. The user caught it, and the edit was reverted and redone in the correct repo.

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HobbiesWent wrong

The AI could not set my fantasy hockey draft rankings

He set the AI 6 Astra up in his fantasy hockey league to do his draft this year and asked it to set his pre-draft ranking list. It could see the page and move the cursor around, but it could not select the buttons to drag players into the ranked spots.

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FoodWent wrong

Order my Chipotle pickup through DoorDash

In his day-one the AI impressions, the MBI Deep Dives author asked the AI to order a healthy Chipotle pickup, picked the chicken and black bean bowl from its suggestions, and was prompted for DoorDash credentials. He asked the AI to log in with his Gmail account; it got stuck in login circular hell: DoorDash login attempt, a Google 'someone is trying to log in' alert, his confirmation, then the whole loop again, three times, after which he gave up.

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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.