During a 30-day trial diary, the author shows the AI filling out a school field-trip permission slip it had found in his email — one of several family-admin tasks it handled from his accounts.
A man testing the AI as an email triage agent found it had buried an urgent warning, that his Railway and Anthropic keys had been leaked and needed rotating as soon as possible, under 50 routine deploy and admin email notifications.
This one went wrong. See what happened before you try it.
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.
His claim was too small for a lawyer and the insurer had frozen it at $4,430, so he worked it himself with AI holding every letter in order. The agent surfaced six dated contradictions in the adjuster's own letters, including a legal basis for denial that changed three times, and reviewed each of his drafts as opposing counsel before anything was sent. After his letter quoting their own paper back at them, the offers climbed: $6,500, then $8,000, then $8,750, and the insurer accepted his split of the last gap the same morning, at $10,250.
He connected his Gmail to an AI task that watched every new email and was only allowed to interrupt him when a message needed action or came from family, with a draft reply ready. All afternoon it alerted him three times, for a bank message, a family email he answered from its draft, and a ticket itinerary change he needed to act on.
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.
He follows the CNN lawsuit over White House press briefing access. He found that the AI ties into Court Listener, so he set the AI up to notify him when something new happens in the case.
This only partly worked. Worth knowing before you try it.
Three family members, three nationalities, one move to Brazil. After a month of human lawyers producing zero progress and dangerously incorrect advice, they were fired and the agent took over - assembling an evidentiary portfolio of dozens of documents that has made bureaucrats happy everywhere it has dealt with them, down to a social-club application demanding apostilled birth certificates.
Without being asked, Harry McCracken's Dot began flagging incoming messages it judged urgent or important in an inbox flooded with PR pitches. It also resurfaced an email from a freelance author that he had overlooked for weeks and nudged him to respond.
A non-developer used AI to restore his foundation's broken donation payments and restructure the portal into four separate funds; the site shows $17,149,000 in donations processed.