You Can Now Invite ChatGPT Into iCloud Mail and Calendar (But Should You?)
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If you’re a ChatGPT fan who doesn’t mind feeding more of your data into the AI machine, then OpenAI has a treat for you. As of this week, you can now connect the platform directly to your iCloud Mail and Calendar accounts.
OpenAI recently shared the news in a post on X, noting that new plug-ins for iCloud Mail and iCloud Calendar are now “available on all ChatGPT plans.”
There’s not a ton of magic to how these new plug-ins work. iCloud Mail and Calendar rely on open IMAP and CalDAV protocols, which is what ChatGPT appears to be using to interface with them.
That means you’ll need to create an app-specific password, just like you would to use a third-party mail or calendar app with iCloud, but it also means that you can simply revoke that password if you change your mind.
Once the integrations are active, ChatGPT will be able to read, schedule, and update events on your iCloud Calendar, as well as search, read, send, and manage messages in your iCloud Mail. This is a direct connection to iCloud on the backend, so the configuration of the Mail and Calendar apps on your iPhone, iPad, or Mac has no bearing on it.
In other words, ChatGPT will only have access to your iCloud data, not any other accounts you’ve set up on your devices. Since iCloud Mail accounts are effectively free, this new integration could be a handy way to give ChatGPT limited access to mail and calendar features — especially if you primarily use another service like Gmail and don’t want to hand over the keys to your whole kingdom.
In a way, these new plug-ins are OpenAI’s response to Siri AI, which can perform similar actions with the Mail and Calendar accounts on your Apple devices — not just iCloud in this case, but any accounts you’ve configured on your iPhone, iPad, or Mac. However, Siri AI handles all of this in a very privacy-conscious way, processing as much as possible on device, and leveraging Apple’s Private Cloud Compute (PCC) infrastructure when it needs more than the on-device silicon can handle.
There have been hints that ChatGPT once hoped Apple would give it the same level of on-device integration. In late 2024, a few months before the Siri improvements were supposed to have rolled out, Apple added a ChatGPT extension to iOS 18.2. This was implemented strictly as a fallback for Siri, allowing users to get broader world knowledge questions answered more accurately. ChatGPT and Siri remained at arm’s length, and Apple never gave ChatGPT the kind of personal context access that Siri AI now enjoys in iOS 27.
However, recent reports have suggested OpenAI expected a greater “payoff” from this deal — both in the form of generating more paying subscribers for ChatGPT and deeper integration across more Apple apps and within Siri itself. Instead, the company felt snubbed by Apple, especially after Cupertino jilted OpenAI to pick Google’s Gemini to build its new Siri AI, effectively leaving the ChatGPT extension to “die on the vine.”
