Find commitments in email that never made it onto the calendar

Josh Dubowsky gave Claude read-only access to Gmail, Calendar, Drive and a laptop for a week; one search turned up 23 dated yeses in the email that the calendar never knew about.

Done withClaudeinGmailGoogle CalendarGoogle Drive· Oct 25, 2026

What they did

Dubowsky connected Gmail, Google Calendar and Google Drive to Claude through its connectors, and used the desktop app to let it see chosen folders on the laptop. In each connector's tool permissions Dubowsky blocked every action that could send, reply, forward, delete or edit an event, and told Claude it could look at everything for seven days but change nothing. Dubowsky then asked it to search six months of email for anything already agreed to, booked, paid for or offered to do with a date attached, check each item against the calendar, and list only the missing ones with the email quoted. A nightly check followed: for each event tomorrow, look through recent email and files for changes, things to bring and clashes.

How it went

The first search took about two minutes and found 23 items: unlogged plans, tickets bought months earlier, favours offered and forgotten, dates that had moved by email, and two bookings on the same Saturday. Six were loose "we must catch up soon" lines that Claude counted as plans. It also confused two people with the same first name and treated a "maybe" as a yes. The nightly check mostly reported no change, but twice that week caught a moved time in an email that had been opened but not read. Claude never tried to send or delete anything.

Worth knowing

Asking for the source email to be quoted is what made the list checkable, since Claude sounded equally sure when wrong. It cannot read attachments, texts or WhatsApp, so bookings sent as PDFs are missed. Whole-mailbox searches use up plan limits quickly. The author sells Claude prompt packs.

Try it

With Claude· 4 parts to fill in

You can read my [email], [calendar] and [files] but must not send, edit, move or delete anything. Search my email from the last [six months] for anything I agreed to, booked, paid for or offered to do that has a date attached. Check each one against my calendar and list only the ones that are missing or whose date has changed. For every item quote the sentence from the email it came from, and flag anything that reads like a loose maybe rather than a real commitment. Stop at the list and wait for me before suggesting any calendar changes.

Square brackets are the parts to fill in. The prompt is ours; the story is theirs.

Where they said it

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