Harry McCracken's Dot, Chip, cross-checked his calendar against his email and spotted that a speaking engagement he had entered on one date had been rescheduled by the organizers to a different day, which the confirmation email showed. He says he would otherwise have shown up to an empty room.
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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Shervin Shaikh asked the AI in chat to find any NYC parking tickets under his name and pay them; after he supplied his licence plate, the AI found a $115 'No Standing' ticket in Brooklyn, now $145 with penalties. The first CityPay attempt failed on a billing-address mismatch, but the retry succeeded: $147.90 paid via Stripe Link, confirmed on screen.
She was using AI to archive legislative material when it flagged a serious vulnerability in a state legislature's website. She had to stop and report it.
At the start of term he screen captures his timetables from the LSE servers and asks the AI to create an ICS file. He can then drop the file straight into his calendar.
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 the same test, he connected Gmail, Google Sheets, and Google Drive; the AI responded to his emails and performed tasks autonomously on its own server even while his laptop was turned off.
Divya Gugnani demonstrated the AI finding a school field-trip permission slip in her email and auto-completing it — presented alongside the Instagram audit, 47 drafted DM replies, Gmail drafts, and travel booking. The reel emphasizes the AI Secure VM and approval-before-send controls.
His inbox gets so much mail that about half of what matters was being missed and a quarter sat in spam. His AI watches the box, sorts what is important, and messages him in a separate chat when something he cares about lands; it took a while to tune the prompt before it matched his judgment.