Since October 27, two new plugins have been available in ChatGPT: iCloud Mail and iCloud Calendar. Once connected, ChatGPT searches for emails in your iCloud mailbox, gives you an overview of your inbox, shows your upcoming appointments, and changes existing calendar entries. The OpenAI release notes list all ChatGPT plans, including the free one, and three platforms: web, desktop app, and iOS.
OpenAI does not make an exception for Germany or the EU. However, the help page generally states that plan, region, and account determine availability. You can see whether the two plugins already appear for you in the ChatGPT settings under Plugins.
How do you connect iCloud to ChatGPT?
Instead of a sign-in page from Apple, you will find a form asking for an address and password. Apple requires an app-specific password for third-party apps. Your regular Apple password therefore belongs neither in this form nor in the chat window.
- First check whether your Apple Account is protected with two-factor authentication. Without this protection, Apple does not create app-specific passwords.
- On account.apple.com, in the "Sign-In and Security" section, you create a new password under "App-Specific Passwords," as described in Apple's instructions.
- In the ChatGPT settings, you select iCloud Mail or iCloud Calendar under Plugins and start the connection.
- For Mail, you enter your address with @icloud.com, @me.com, or @mac.com; for the calendar, the main email address of your Apple Account. The two addresses can differ.
You connect Mail and Calendar separately; one plugin does not unlock the other. Both plugins read your contacts but do not change your address book. Separate plugins for contacts and reminders are not included at launch, as OpenAI writes on the help page on connected accounts.
What happens to your emails?
OpenAI names four tasks: finding emails, going through the inbox, displaying appointments, and changing appointments. OpenAI does not mention sending or deleting emails.
If you use ChatGPT Free, Go, Plus, or Pro, OpenAI may use content from connected apps to train its models as long as the model improvement setting is turned on. For Business, Enterprise, and Edu accounts, OpenAI does not use this content by default. With the Memory feature turned on, ChatGPT can also store details from retrieved emails. Customer correspondence of self-employed people can thus end up in training material or in the Memory feature's storage.
What distinguishes iCloud from Gmail and Outlook?
ChatGPT already offers such connections for Google and Microsoft accounts; there you grant access on the provider's sign-in page. With iCloud, the Apple service is now added, for the time being without an Android app: OpenAI mentions only web, desktop, and iOS.
If you disconnect in ChatGPT, the app-specific password remains valid at Apple until you revoke the password there yourself. Conversely, if you change your Apple password, Apple automatically revokes all app-specific passwords, and both plugins need a new one.
What this means for you
It is best to create a separate password with a clear label for each plugin, such as "ChatGPT Mail" and "ChatGPT Calendar." Apple allows up to 25 active app-specific passwords. With separate passwords, you can later revoke a specific connection without signing out other apps.
Before you connect a mailbox containing customer emails, take a look at ChatGPT's privacy settings. If you do not want any customer correspondence to flow into training, turn off model improvement. The Memory feature can also be turned off.
How to precisely formulate prompts for search requests such as "Show me all invoices from October" is something you can practice in the ChatGPT Masterclass on TutKit.
OpenAI introduced the plugins on October 27, 2026.
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