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Let ChatGPT find your emails and fix your calendar, explained by monkey

comment: CALENDAR

ChatGPT can now plug into your iCloud Mail and iCloud Calendar, on every plan including Free. Ask it to find that one email you lost, or move an appointment to tomorrow, in plain words. Here's how to connect it, what to ask, and the one safety step most people skip.

On October 27, OpenAI added two plugins to ChatGPT: iCloud Mail and iCloud Calendar. They work on every ChatGPT plan, including Free, on the web, in the desktop app and on iPhone. Once they're connected, you can ask ChatGPT to search your email, catch you up on your inbox, check what's next on your calendar, and add or move events.

Before you start

  • Mail only works with an iCloud address: one ending in @icloud.com, @me.com or @mac.com. If you added Gmail or Outlook to your iPhone's Mail app, ChatGPT can't see those through this plugin.
  • Calendar uses the main email of your Apple Account, which can be different from your iCloud email.
  • Your Apple Account needs two-factor authentication turned on.
  • The Android app isn't on OpenAI's list yet. Use the web, the desktop app or an iPhone.

How to connect it

  • Go to account.apple.com, open Sign-In and Security, and make an app-specific password. Give it a name you'll recognise, like "ChatGPT".
  • In ChatGPT, open Settings, then Plugins.
  • Pick iCloud Mail, sign in with your iCloud email and that app-specific password.
  • Do the same again for iCloud Calendar. They connect separately.
  • Never type your normal Apple password, and never paste any password into a chat message.

Things to ask

  • "Find the email with my dentist appointment."
  • "Catch me up on my inbox from this week."
  • "What's next on my calendar?"
  • "Move my dentist appointment to tomorrow morning."
  • "Does my Thursday meeting clash with anything?"
  • "Find a free hour on Friday for lunch with Sam."

It can also draft and send emails and look up your contacts, so read anything it writes before you let it go out.

The safety step most people skip

Disconnecting the plugin in ChatGPT does not cancel the password at Apple, and app-specific passwords never expire. If you stop using it, go back to account.apple.com, open Sign-In and Security, and delete that password (or use Revoke All).

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