ChatGPT can work with your iCloud Mail and Calendar thanks to new plugin support

You can use the AI assistant to update calendar events and search your inbox, among other things.

OpenAI

OpenAI has added support for Apple's email and calendar services to ChatGPT. Thanks to new plugins for iCloud Mail and iCloud Calendar, the AI chatbot can now work with iCloud in the same way that it can with Gmail and Google Calendar.

The company says once the plugins are enabled — you'll have to log in with an Apple account and create an app-specific password — ChatGPT will work with either service across desktop, the web and iOS, regardless of whether you have a free account or pay for a ChatGPT subscription. If you pay for OpenAI's Pro plan, your Dot, the company's AI agent, can also use either plugin.

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

You can use ChatGPT to read and manage iCloud emails or calendar events with just a prompt. These plugins are different from letting ChatGPT interact with Apple's Mail and Calendar apps on macOS directly, though. Both apps can display inboxes and calendars from third-party services like Outlook or Gmail. The iCloud Mail and iCloud Calendar plugins will only give ChatGPT access to the messages and calendar events associated with Apple's services, so they're useless if you don't use iCloud.

The fact that OpenAI is offering these at all is an interesting expression of the complicated relationship the company has with Apple. ChatGPT was the first AI assistant to be directly integrated with Siri. Apple's decision to work with Google rather than OpenAI to revamp its AI models was the first suggestion that the relationship had soured. Apple's July lawsuit alleging OpenAI employees stole its trade secrets only furthered that impression. And yet, alongside the new M6 iMac and MacBook Pro, Apple announced Creator Studio updates that include a new chatbot experience, partially powered by OpenAI models, in Pages, Numbers and Keynote. Neither company seems willing or able to fully walk away from the other.