ChatGPT users who keep email and schedules in iCloud can now connect those accounts so the assistant can search messages, summarize recent threads, draft and send replies, and create or update calendar events. OpenAI announced the plugins on October 27, 2026, and they are available on all ChatGPT plans, including the free tier, on the web, desktop, and iOS. The release gives iCloud users the same style of account connection that Gmail and Google Calendar users already had. Each service connects as a separate plugin and requires an Apple app-specific password rather than a standard Apple Account sign-in. The mail plugin covers only addresses ending in @icloud.com, @me.com, or @mac.com, so Gmail, Outlook, and other accounts added to Apple's Mail app stay out of reach unless connected on their own. The calendar plugin uses the primary Apple Account email, which may differ from the iCloud mail address, and both plugins include read-only contact lookup. These connections also open iCloud data to Dots, OpenAI's proactive agent, for the first time. A single request can search an email for event details, check the calendar for free time, and add the event.