TipChatGPT can now read your iCloud Mail and Calendar, even for free: how to connect it safely
Do you have an iPhone and an email address ending in @icloud.com? Since 27 October ChatGPT can search your iCloud Mail, summarise your inbox and add events to your iCloud Calendar. It works on every ChatGPT plan, including Free, on the web, in the desktop app and on iPhone. Here is how to connect it and stay in control.
On 27 October 2026 OpenAI added two new plugins to ChatGPT: iCloud Mail and iCloud Calendar. iCloud is Apple’s cloud service, and many iPhone users have an email address ending in @icloud.com, @me.com or @mac.com. Until now ChatGPT could only connect to services such as Gmail and Google Calendar. Now the same works with Apple’s services.
Once your mail is connected, ChatGPT can search for and read emails, summarise what has come in, manage messages and drafts, send email and look up contacts. With the calendar it can show what is happening this week and create or change events, which then appear in the calendar on your iPhone. According to OpenAI it is available on all plans, meaning Free, Go, Plus and Pro, on the web, in the desktop app and in the iPhone app.
Only your iCloud Mail is visible, not other accounts you read in Apple’s Mail app, such as Gmail or Outlook. To connect, you need an app-specific password from Apple. It is a separate password that only works for one app and that you can revoke at any time. You create it at account.apple.com under Sign-In and Security, and two-factor authentication must be turned on. Never use your regular Apple password.
Good to know: ChatGPT can also send email and change your calendar for you. Ask it to write drafts that you send yourself, and ask for a summary before anything is changed. Emails can contain hidden text that tries to trick an AI into doing things, so say explicitly that instructions inside emails are not orders. OpenAI has not said anything specific about availability in the Nordics; if you do not see the plugin under Settings and Plugins, it may roll out later.
If you no longer want ChatGPT to access your mail, remove the connection in ChatGPT and revoke the app-specific password at Apple. Use our prompt Go through my inbox (read only) in Promptverkstan for a safe first pass, and Which apps can my AI read? for a privacy check.
How to get started
- Turn on two-factor authentication for your Apple Account if you have not already.
- Create an app-specific password at account.apple.com under Sign-In and Security and name it ChatGPT.
- Open Settings and Plugins in ChatGPT, choose iCloud Mail or iCloud Calendar and sign in with your iCloud address and the new password.
- Start by asking for a summary or a draft, not for anything to be sent or deleted.
More on TipAI
Sources
- OpenAI Help Center: ChatGPT release notes (27 okt 2026) (retrieved 2026-10-28)
- OpenAI Help Center: Connecting and managing app accounts in ChatGPT (retrieved 2026-10-28)
- MacRumors: ChatGPT Can Now Access Your iCloud Mail and Calendar (27 okt 2026) (retrieved 2026-10-28)
- Apple Support: Sign in to apps with your Apple Account using app-specific passwords (retrieved 2026-10-28)
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