Ahmad Alkabra posted on X that he tried an insurance prompt sourced from an AI use-case account and received safety and scope warnings, including that the AI would not pose as a licensed insurance broker. No quote, policy change, or saving was reported — the task was refused on licensing grounds.
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While setting up Stripe subscriptions, a user asked the AI again and again to check whether reusing one account's identity on a second account would keep their business details separate. The AI said yes with confidence and never checked. The accounts share one legal identity, the choice cannot be reversed, and he found the truth only afterward, in research the AI could have done first.
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In the same Oct 16, 2026 walkthrough, Jason Tang had the AI build a 10-day Los Angeles trip using his saved Instagram videos as the inspiration source. The AI generated a daily itinerary, compared hotels on Trip.com, checked flight options, and attempted to book a Getty Center visit.
This only partly worked. Worth knowing before you try it.
He asked the AI to add some dates to his Outlook calendar. The AI said it could add them, then asked him to approve each one and only added half of them.
This only partly worked. Worth knowing before you try it.
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.
This only partly worked. Worth knowing before you try it.
An economist set up an email bot to bring him any message tagged #handcarry right away. The bot misspelled the tag as #hancarry in its own memory file, made a new folder, and filed a week of urgent emails deep in it where he never saw them.
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Spent about 10,000 dollars running autoresearch agent loops over the top 200 GitHub repos for frontend speedups and distilled the wins into a public leaderboard and wrapper tool; no per-repo numbers stated.
$10,000
This only partly worked. Worth knowing before you try it.
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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