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ChatGPT can now read your iCloud Mail and Calendar

OpenAI has added iCloud Mail and Calendar plugins to ChatGPT, letting Apple users connect their inbox and calendar the same way Gmail users already could. The plugins work on all ChatGPT plans across web, desktop, and iOS.

A person's hand opening a mailbox while a calendar page floats nearby, symbolizing email and scheduling integration.

OpenAI has launched iCloud Mail and Calendar plugins for ChatGPT, available on all plans on web, desktop, and iOS. Apple users can now ask ChatGPT to search their inbox, catch up on unread messages, check upcoming events, or update a calendar entry.

What happened

On 27 October, OpenAI announced the new plugins via the official ChatGPT account. The announcement stated: "Much requested, and now yours to connect: iCloud Mail and Calendar plugins are available in ChatGPT. Ask ChatGPT to find that email, catch up on your inbox, check what's next, or update a calendar event."

The plugins are available on all ChatGPT plans. To connect them, you create an app-specific password inside your Apple ID settings and use it to sign in, the same approach other third-party apps take when linking to iCloud Mail and Calendar.

The update also switches on ChatGPT Dots for iCloud users. Dots is an agent, meaning an AI that completes a task with several steps for you, not just one answer. It runs in the background and can now draw on your Apple mail and calendar data. Previously, Dots worked with other connected services but not iCloud.

What it means for your work

  • You can ask ChatGPT to find a specific email without opening the Mail app.
  • You can ask it to summarise what is on your calendar for the rest of the week.
  • You can ask it to update or check a calendar event by describing it in plain language.
  • Dots can now proactively surface reminders or follow-ups based on your iCloud inbox and calendar.

What to do now

  1. Open ChatGPT on web, desktop, or iOS. You do not need a paid plan.
  2. Go to the plugins or connected apps section. The exact menu path is not public yet, so look for a connections or integrations area in settings.
  3. Choose the iCloud Mail or iCloud Calendar plugin.
  4. When prompted, enter an app-specific password. You generate this inside your Apple ID account settings at appleid.apple.com under the Sign-In and Security section.
  5. Once connected, type a request such as "Find the email from my accountant last week" or "What meetings do I have tomorrow?"

Note that the announcement specifically mentions web, desktop, and iOS. It is not yet clear whether the plugins work on Android.

The plugins are a straightforward way to bring your Apple data into the same conversation where you already ask ChatGPT questions at work, without switching between apps. 9to5Mac