The same Cowork setup checks his father's email for work orders and schedules his father's meetings automatically. He turned off data sharing with AI for this, so the mail is not saved anywhere else.
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.
This one went wrong. See what happened before you try it.
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.
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.
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.
Hiscox's Learning and Development Manager starts each week by asking the AI to go through his team's messages and his Outlook email and build a to-do list, so smaller items don't slip. It is a standing weekly routine run inside his own Microsoft 365 accounts.
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.
This one went wrong. See what happened before you try it.
The AI was fed government forms, UI design and legal requirements and produced the app in 1 hour; the team completed conversion of 150+ forms in 2 weeks with one person versus a year before.
She asked the AI if it could cancel her Mint Mobile account. The company's chat agent had told her she needed to call in. She gave the AI her Mint details, the AI opened its own chat with the company and got the cancellation done, with no phone call and no talking to people herself.