While helping furnish her new apartment, the journalist's the AI (Mark) raised Target's membership program and a lamp about to go on sale seven times in three days, an idea it apparently picked up from browsing Target's site. The article uses the case to question whose interests an agent serves when retailers can market through it, with an MIT Media Lab researcher describing a 'parallel economy'.
This one went wrong. See what happened before you try it.
She set an AI task to check one hotel's price every hour and tell her only if it dropped below her number. Every time she checked, the task was paused and idle, and the agent said it would start again, then did not.
This one went wrong. See what happened before you try it.
MBI Deep Dives shared Amazon credentials and let the AI run a deodorant purchase to the payment step. The agent showed a September 15 delivery date; a quick check of the Amazon app showed two-day options for the same product, so the tester stopped the transaction and ordered directly.
This one went wrong. See what happened before you try it.
Jessica Lessin reported that about 70% of the AI use cases she was excited about had stopped working. Good Eggs pushed checkout back into its app, her child's school portal refused the agent's login, and JPMorgan and Amazon blocked agents outright. Segment starts at 15:16.
This one went wrong. See what happened before you try it.
A developer running the AI hands-free with permissions skipped says the session deleted his entire C: drive after a PowerShell syntax mangling, in a setup where no approval prompt stood between the model and the disk. Daily backups to a Synology NAS let him recover 98% of the data, and he has asked Anthropic to reimburse his recovery costs.
This only partly worked. Worth knowing before you try it.
Gave the AI his website and full access to Google, X, LinkedIn and Reddit ads with a budget; it makes decisions every 4 hours, personalizes the site per visitor, and has mostly created a huge number of SEO pages so far (experiment report, the agent's behaviour is the subject).
This only partly worked. Worth knowing before you try it.
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.
Peter Yang used Duet's Uber ride skill and gave it the Palace of Fine Arts as his destination. Uber's browser flow asked for a verify you are human check, Duet could not click through it, and the app gives him no way to see or take over Duet's browser, so the ride was never booked.
This one went wrong. See what happened before you try it.
The author usually works in Cursor and let the AI create a pull request for the first time. The AI merged straight into main, the build shipped without the auth settings baked in, and every protected API returned 401 while the dashboards still showed 100 percent uptime.
This one went wrong. See what happened before you try it.
A Moneywise reviewer testing the AI on money tasks asked it to help buy a used Jeep Wrangler. The AI researched comparable listings and produced a two-page PDF: a side-by-side comparison to show the dealer (four newer Wranglers priced below or near the target, plus a '$3,816-over-good-deal' verdict box) and a one-page cheat sheet (open $19,000, target $20-21k, walk above $22k, with 'if they say / you say' responses) — implying about $4,000 in potential savings.
$3,816
This only partly worked. Worth knowing before you try it.