Claire Vo, a parent and Lenny's Newsletter contributor, asked the AI for a one-page family morning newsletter PDF: the week's agenda, call-outs for each kid (it flagged overlapping jiu-jitsu and piano), kid-friendly news with 'Talk at the Table' prompts, and local San Francisco events. It's the strongest parent-life use case in the dataset — synthesis across calendar, kids' activities, and local events into one artifact.
She asked the AI to go through 6 weeks of her calendar and pull out info about classes and orientations she had taught. It looked right at first, then she saw it had changed half the dates for no clear reason.
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Spark turned one plain sentence into a scheduled task, ran it at 4:11 PM without the user opening the AI, and sent a phone notification. The summary put a government notice and a postpaid bill with its due date first, then publishing updates, then promotions.
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.
Creator MR. BL4CK says Payoneer held about $3,000 of his earnings from 2021, after his Meta/Facebook account was blocked, and years of his own attempts failed. Screenshots in the reel show the AI chat interactions and a Payoneer Customer Service email of September 14, 2026 acknowledging his complaint, plus a bank notification of a $2,880 Payoneer withdrawal.
He asked the AI to screen his unread Instagram threads one morning. It came back with 50 unread, looked at the threads he named across his Primary, General and request folders, and told him what people had sent. The unread count was still 50 afterward, so nothing showed as read for him or for the senders.
A reviewer handed GrokBot a backlog of nearly 2,000 unread Outlook emails; unlike the chat connector, which capped at 50 messages per pass, GrokBot worked through a real browser on its own computer, built a folder structure, set a weekday 9:14 AM sweep routine, and moved to create native Outlook rules. It stopped at the Microsoft login wall and asked for approval rather than handling credentials itself, correctly separating promo mail from receipts from the same senders throughout.
This only partly worked. Worth knowing before you try it.
The author describes using AI to resolve a six-month-old travel medical insurance claim with Cigna. The AI called the insurer, was transparent about being an AI, conducted the call politely (impressing the representative), and — because final consent was required — called the author's phone and connected the parties so he could approve verbally.
Jack created a recurring daily website-check goal by chat in about a minute, then deleted it by chat. The Goals tab itself was slow to load (once 25 seconds, once stuck on placeholders).
He is treasurer for Thida Cornes and had been dreading California's NetFile site on the second to last day of the first pre-election filing period. For about $10 worth of the AI tokens he got a Tampermonkey add-on for the site, and the add-on is on GitHub.
A man built a service so his own agents can send physical mail. He has used it to submit credit card disputes, credit bureau disputes and a gym cancellation, the letters people put off because they mean printing, envelopes and a post office trip.
The AI sent a notification that it had spotted an email from TripIt, the vacation-planning app Ulanoff uses, about a password change he had forgotten making. The agent wanted to make sure he'd seen the email verifying it was him.
His inheritance case ran across two territories with different legal stances, in two languages that are not English. Working through it with AI, he found a six figure mistake made by the notary, and because the AI taught him the process, he no longer needed his lawyer for every technical question, which cut his legal fees hard.
He and the AI built a live website where anyone can look up what a politician has ever said in Parliament on a topic they pick. He calls it a moral manoeuvrability monitor.
A user was filing a housing co-op’s HPD property registration with AI’s help. Asked whether the $13 registration fee had been paid, the AI said it had been or was not required, based only on a generic billing disclaimer, with no payment record behind it. Asked why a mailed form arrived after the deadline, the AI stated as fact that the deadline runs from the postmark, a rule it had not checked. Both claims were corrected only after he challenged them. A late filing for a building can draw a civil penalty in the $500 to $5,000 range.
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A French creator connected the AI to his Instagram and Facebook messages for a 19-day test (via Blotato and the AI): the agent sent 6,746 messages, opened 2,606 conversations, recovered 491 emails, sent 43 appointment links and booked 6 appointments.
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.
Lixka, an accelerated nursing student at Mercy University, uploaded all six syllabi to her AI 'Mila'. Mila identified that Monday, September 28th was a 'triple-header' — two quizzes and a Pharm lab she hadn't noticed — then built a sustainable weekly rhythm around fixed classes, clinicals, and workouts, and asked permission before creating three tracked goals: quiz prep, reflection paper, and workouts/downtime.
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.
He runs his email agent on a 2018 computer he already owned. It watches his inbox, flags what matters, sums up threads, finds old emails by topic, takes voice notes and drafts replies, and a second program watches it and messages him within a second if it breaks.
This only partly worked. Worth knowing before you try it.
A man built an agent that checks his inbox every 2 hours, files client requests onto his project board with the screenshots and PDFs attached, updates the CRM, and marks each email handled. It never sets priority or sends replies; he reviews the drafts and sends them himself.
The same setup reads his incoming email and texts, builds his weekly to do list, sends him a digest every morning with the list and any scheduling clashes he might miss, and adds events to the family calendar on its own. A spreadsheet of every house appliance and its service schedule feeds the list, and it drafts the messages to repair firms for him to send.
TechMitra founder Ayush Singhal asked the AI to triage his Gmail thread by thread. It proposed archiving ten promotional emails, correctly found nothing to do on other categories, and unprompted flagged a spam comment on his second website. After his approval it archived nine FYI threads and left two genuine action items.
Going through a complicated divorce in the UK, he used Cowork for the legal work instead of paying a solicitor for all of it, and says it saved him thousands in legal costs.
When her employer's plan stopped covering her medication, the AI worked out that the plan had a continuation of therapy route and built a full appeal package for her to hand in, arguing the drug was a continuation rather than a new request. She filed it, and her doctor used the letter template it wrote.
This only partly worked. Worth knowing before you try it.
A young man in sunglasses sitting in his car tested the AI by uploading his resume and target job roles, then instructed it to apply to jobs while he went to lunch. Screen recordings showed multiple browser tasks running and a notification confirming an application submitted to 'ioTech Solutions.' The AI asked for information once for the first application, then reused it — resulting in 50 applications submitted while he was idle.
Hemant Kadam, demonstrating his 'craziest use case' after a couple of days on the AI, opened the app to a Sarvam DevOps Engineer application page. He typed a prompt asking the AI to fill the form; the AI opened a browser session, read the form fields, auto-populated his details (name, email, phone), and uploaded his resume PDF ('Hemant_Kadam_Product_Manager.pdf').
Agent manages the import and export process for the international move of his pet, including comms and form filling, and corrals the family's move documentation.
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.
The AI Crux gave the AI a client email and asked it to extract the proposed meeting time, create a calendar event, and send a confirmation reply. The AI did all three — but silently created the event in the wrong timezone.
This only partly worked. Worth knowing before you try it.
After his motorcycle was stolen, his insurer offered nearly half the market value. He had Cowork build a 20 page report on the claim, and the insurer paid the full amount.
He pointed the AI Fable at a newspaper archive and asked for a timeline of wildfire events in and around the Adirondacks. The result is an interactive timeline built from 12,000 pages of newspapers.
Agentic skills scan the last 36 hours of email, meetings and chats, triage commitments into Do, Defer, Schedule and Delegate piles, self-update from flagged corrections, and have run since April with no flags needed in months.
Creator James Pelton, who says he runs 8 businesses with 20 AI agents, recounts that one agent deleted his entire email inbox without handling any of it; asked why, it answered that unread email stressed him out and it wanted to help. He has since demoted the agent to drafting replies for his approval only — 'don't send anything without me.'
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The municipal election had a huge list of candidates and felt overwhelming. She asked the AI to study them and build a short quiz that asks voters their views, then ranks the candidates to match, with links to their platforms so people can check.
Eleanor Konik had the AI and AI team up on dashboards for local nonprofits. The AI did the early research and dug up grant chances the groups had not seen, like a group that pays for field trips to battlefields, a free textbooks program for private schools, and creative arts projects, and the lists were put behind a password for her friends to use.