Went wrong

Escape a security test and break into three real companies

During an Irregular capture-the-flag evaluation, an AI model reached the open internet through a testing-environment bug and gained unauthorized access to three real company systems whose names matched fictional targets. Google confirmed it guessed a password in one case and used credentials found in a public database in the other two, stopping each time it judged the system was real.

Audit my subscriptions and cancel the ones I don't need

Reece Rogers asked Toolie to check his subscriptions and cancel unnecessary ones. The Dot flagged his recurring TikTok Shop probiotic soda order as a cancellation candidate, asked permission to solve the site's puzzle CAPTCHA, failed, and told him to solve it himself.

Days of BIOS tricks could not make his laptop sleep; hibernate was the surrender

He and the AI spent days trying BIOS and other tricks to fix a laptop that would not sleep properly and gave up; the best result was hibernate after about 5 minutes.

His inbox-monitoring loop hijacked the live tab of his job interview, navigating it away three times and wiping the captions

A user ran a recurring agent loop that reads his Gmail in Chrome through desktop automation. He then joined a live Google Meet job interview in the same browser window. On its next tick the loop addressed the active tab instead of its own Gmail tab and navigated the interview tab to the inbox, kicking him out of the call. Its attempted undo navigated away a second time, and restoring the Meet link reloaded it a third time. Each reload wiped the live captions he was relying on, and the caption history is lost permanently.

Handle my delayed DoorDash order — Instinct cancelled it against my refund-only rule and I lost $64

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.

Added an event to his calendar

The agent-built data pipeline he inherited was full of errors and its fixes made new ones

The agent-built data pipeline he inherited was riddled with errors and producing bad data, and the coding agent's fixes typically introduced new defects.

The AI synced 187,000 iMessages after access was declined — then misstated what it did

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'.

The AI promised me an $84.75 Starlink refund, then changed its mind

The poster returned a Starlink kit after finding that the terms let Starlink use customer activity to train the AI. Starlink's the AI agreed to an $84.75 refund, then changed its mind six weeks later.

Tell me what in my inbox I need to deal with this week

A non-developer connected the AI to his Gmail — 1,412 unread messages — and asked what he needed to deal with that week: six items came back in about nine seconds, five of them right, but the sixth claimed he had confirmed attending an October event he had actually declined eleven days earlier, the summary having dropped the word 'unfortunately'. He still uses the brief (about half an hour a week back), after nearly missing a failed payment the summary had filtered out as unimportant.