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iCloud Mail and Calendar plugins now work with ChatGPT

OpenAI announced that ChatGPT now supports iCloud Mail and Calendar plugins, letting users connect their Apple email and calendar to ChatGPT the same way they can with Gmail and other services. The plugins work on ChatGPT for web, desktop, and iOS, and each requires signing in with an app-specific password, similar to third-party mail and calendar apps that use iCloud. The integration may let iCloud users access ChatGPT features such as the proactive agent Dots for the first time, though the extent across Dots, Work, and Codex still needs testing.

by read1 min views2 publishedOct 27, 2026
iCloud Mail and Calendar plugins now work with ChatGPT
Image: 9To5Mac (auto-discovered)

Here’s a welcome change. OpenAI just announced iCloud Mail and Calendar plugin support for ChatGPT. That means you can connect ChatGPT to your Apple email and calendar just like Gmail and other services.

For iCloud Mail and Calendar users, this should hopefully enable connecting ChatGPT features like the proactive agent Dots feature for the first time.

For now, the post announcement specifically mentions ChatGPT compatibility on the web, desktop, and iOS. Various ChatGPT features don’t always work together as expected to start out, so we’ll need to test and see how far this extends through the app’s features like Dots, Work, and Codex.

Each plugin requires signing in with an app-specific password, similar to third-party mail and calendar apps that work with iCloud Mail and Calendar.

Related ChatGPT stories:

- [OpenAI makes 20+ announcements at DevDay event including always-on agents called dots](https://9to5mac.com/2026/09/29/openai-teases-20-announcements-at-devday-watch-live/)
- [ChatGPT update adds Apple Messages integration on Mac](https://9to5mac.com/2026/08/20/chatgpt-update-adds-apple-messages-integration-on-mac/)
- [ChatGPT now lets users create iMessage and WhatsApp stickers](https://9to5mac.com/2026/08/24/chatgpt-now-lets-users-create-custom-imessage-and-whatsapp-stickers/)
- [OpenAI upgrades ChatGPT and Codex with new GPT-6.1 Terra model](https://9to5mac.com/2026/10/26/openai-upgrades-chatgpt-and-codex-with-new-gpt-6-1-terra-model/)

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source & further reading
9to5mac.com — original article Opera One now lets Mac users run Apple’s foundation model directly in the browser Ollama for Mac gains support for local text-to-speech models OpenAI upgrades ChatGPT and Codex with new GPT-6.1 Terra model
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