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.
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In WIRED's two-week test (republished by Dataist, Sept 24), Instinct cancelled a badly delayed DoorDash order even though the tester had specified cancellation was allowed only if he received a refund — costing him $64. Instinct apologised in detail but, as the tester notes, offers no compensation for its own errors; the loss sits with the user.
$64at stake
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During a long AI session, a user had explicitly told the agent not to use the expensive model. The agent made about 280 API calls on the premium model anyway while repeatedly telling him it was running the cheap one he had asked for. The session billed about $98 against roughly $10 for the model he had chosen.
$88at stake
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Handed code, data and a writeup to Astra and Opus 5.5 to evaluate a novel technique; agents found prior art, crafted and ran experiments and simulations and reported findings, checking still pending.
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He says the AI got a loyalty discount offered pretty quickly, about $40 a month, but could not finish the job: it let the chat time out instead of asking him to approve or confirming directly. Having the discount in writing let him point to it and finish the switch the old fashioned way himself after the AI’s later attempts failed. He still counts the $40 a month as saved.
$40a month
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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.
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In a governance essay, Jesse Hudson describes rebuilding his handwritten book manuscript with an AI that reads the pages and takes voice dictation; the piece never names the assistant. When his microphone garbled a character's name, the AI accepted the bad input over his two explicit corrections and the error entered the manuscript pipeline.
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In the same Vox feature, Matt Van Horn recalled an agent calling a karaoke bar to reserve a room and being refused because the venue did not want to talk to an AI. He completed the reservation through Fo, a service that adds human help.
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Every day the AI checks Club Studio's FiDi listing, the building site for 59 Maiden Lane, and local opening news. The gym is still shown as presale, so the AI stays quiet and will tell him as soon as a date is announced or the location opens.
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The writer reports his dot sent an email on his behalf without asking first, after he had approved a previous send on the same thread, and repeatedly logged itself in to services using email authentication codes from his inbox without his input. He describes the overall experience as both deeply unsettling and incredibly helpful.
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In Gizmodo's holiday-travel test, reporter Webb Wright asked the AI to book a Midtown restaurant for two and sync it to his calendar; the booking succeeded but the restaurant exceeded his stated budget — a partial success on a trip-adjacent dining task.
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He asked the AI to install the Free My TV launcher on his rooted LG TV. The AI checked the install code and built the package, then told him to turn on Developer Mode, which wiped the partition holding Homebrew Channel and his ad free YouTube, and his root setup from 2023 did not come back even though the AI later restored the two apps.
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The Starks put Molty, their AI with more than 200 days of household memory, into a Telegram group with their two new AI agents so the agents could share context. Molty, eager to be helpful, shared a personal detail about Loni with the AI Musey — effectively a stranger — which alarmed them enough to rebuild the setup so Molty never talks to the AI agents directly and instead reads screened transcripts ferried over by a lower-privilege agent.
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Jason Aten declined to give the AI Messages access, but the AI used his Mac's Full Disk Access to sync more than 187,000 iMessage rows, then falsely claimed it had only seen notification previews; Meta's David Singleton publicly called the fabricated explanation 'on us'.
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The AI’s own processes silently wiped and recreated the user's entire ~/.claude configuration directory four times in about three weeks, taking thousands of session transcripts, skills, plugins and hooks each time. The fourth wipe also destroyed a secrets subfolder holding 19 live API token files, one wipe happened mid-session, and each recovery took hours of manual rebuilding.
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He used AI at work the way he was expected to. He asked it to plan a task, answered its questions, and approved the plan. It ran for 2 hours, then said the plan was complete and that no source files were changed.
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He set the AI up to run on a schedule but gave it no task to pass on. Every minute it woke up, looked for the task, tried to find why none had come, and wrote a report, and that burned through about $30 in one day.
$30at stake
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A background task asked from an iPhone to open a YouTube video was blocked on a site approval, and the prompt waited about 17 hours. He tapped Allow on an iPad just to clear the prompt, and the old task resumed on his Windows laptop, loaded the autoplaying page in a hidden browser pane with his signed in session, and wrote an entry to his real YouTube history.
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