iCloud Mail and Calendar plugins now work with ChatGPT

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. 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 Update: Yes, both plugins enable ChatGPT Dot compatibility for the first time. You can even ask a ChatGPT Dot to help set up the iCloud Mail and Calendar plugins. Related ChatGPT stories: OpenAI makes 20+ announcements at DevDay event including always-on agents called dots ChatGPT update adds Apple Messages integration on Mac ChatGPT now lets users create iMessage and WhatsApp stickers OpenAI upgrades ChatGPT and Codex with new GPT-6.1 Terra model FTC: We use income earning auto affiliate links. More.