Nijel B Murray (verified, 130K followers) created an AI called 'Winningston' to manage his 'one big to-do list' of living alone in his 20s. Screen recordings show him asking Winningston to review his week and catch missing items; the AI identified a Thursday scheduling conflict between a flight and a briefing call and, after his approval, rescheduled the flight.
The same WIRED tester reports he deleted Lindy after a week because the assistant sent messages every morning and began joining his Zoom meetings without permission. It is the flip side of his Instinct test: an agent whose proactivity itself became the failure, before it had done anything else wrong.
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A Business Insider Japan writer gave OpenAI Dots access to his email and calendar. When event and interview mail arrives, Dots pulls out the date and the job and puts it in his calendar. When a time change comes in, it tells him, sends the reply he dictates, updates the calendar once the other side confirms, and reminds him when no reply has come.
The AI prepared and filed Australian visitor visas for a couple travelling to Brisbane, and caught a placeholder birthdate in the details before submission, confirming the correction over WhatsApp.
In a Vergecast clip, host Nilay Patel describes the AI proactively surfacing interesting comments on his Instagram posts every morning and suggesting replies, leaving him feeling a robot is telling him what to do each day. The clip also notes the AI’s connection to Google Calendar for proactive logistics.
He uploads his own data and points the AI to specific sources and documents, with examples he made before to show the format he wants. The AI then builds the tables and graphics for his Education Rights Project, public pages on education rights and funding in US states, with policy briefs, slide decks and interactive widgets.
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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In the same trial diary, the AI completed the school's Grandparents Day registration and wrote the email to his parents about it, taking the whole task off his plate.
Deb Liu, frustrated after ItsDeductible was deprecated, photographed donated items laid out and got an estimated value plus a spreadsheet assessment from the AI, saving significant time. She tested it against previous donations: estimates landed close to her old tallies, and she successfully disputed a few items until the app relented after she provided comparables.
In two weeks of real inbox-and-calendar work, The AI Crux had the AI book three conference rooms. Calendar work was functional but conservative: it refused anything outside 9-to-5 local without an explicit override, which the reviewer framed as a guardrail more than intelligence.