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ChatGPT finally gets the iCloud Mail and Calendar plugins users have been waiting for

Apple users can now search emails, draft replies, and manage appointments directly through ChatGPT.

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Rachit Agarwal / Digital Trends

Two new highly requested iCloud plugins just got added to ChatGPT, giving people who rely on Apple’s Mail and Calendar services a way to search emails, check appointments, and manage their schedules directly through the chatbot.

The integration is rolling out to all ChatGPT plans, including the free tier. You can access it on the web, desktop, and iOS.

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. Phew.

Available on all ChatGPT plans on web, desktop, and iOS. pic.twitter.com/g68OWoFVg8

— ChatGPT (@ChatGPT) October 27, 2026

Your inbox and calendar can now work together

Imagine you have a meeting coming up but cannot remember the details. You could ask ChatGPT to find the confirmation email, check whether it clashes with anything else on your calendar, and help reschedule an appointment if needed.

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The Mail integration also supports searching for messages from specific people, summarizing recent conversations, drafting replies, and sending emails. Calendar support extends to creating and updating events, while both plugins can look up contacts.

How to connect iCloud Mail and Calendar to ChatGPT

To get started, users need to open Settings > Plugins in ChatGPT, find iCloud Mail and iCloud Calendar, and connect each service separately. Apple also requires an app-specific password for both connections. You can generate one by signing in to account.apple.com and heading to Sign-In and Security > App-Specific Passwords. Two-factor authentication must be enabled on your Apple Account.

Once you have the password, return to ChatGPT to complete the setup. The Mail plugin requires an email address ending in @icloud.com, @me.com, or @mac.com, while Calendar uses your primary Apple Account email address, which may be different. Enter the generated password instead of your regular Apple password.

There is one limitation worth knowing. ChatGPT can only access emails stored in iCloud Mail through this plugin. Gmail or Outlook accounts added to Apple’s Mail app won’t be accessible unless you connect those services separately.

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Sudhanshu Kumar Mangalam
Sudhanshu Kumar Manglam is a tech journalist at Digital Trends, where he covers consumer technology, science, and games.
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