KeeploopKeeploop or ChatGPT's iCloud and Apple Messages plugins?
Which is better, ChatGPT's own Apple plugins or Keeploop?
If your mail is iCloud Mail and ChatGPT is your only assistant, OpenAI's own plugins may be all you need. The iCloud Mail and Calendar plugins work on every ChatGPT plan, on the web, desktop and iOS, and the Apple Messages plugin reads and sends texts from ChatGPT on an Apple silicon Mac. Keeploop fits when your mail includes Gmail, Exchange or other accounts in Apple Mail, when you also want Notes, Slack and Contacts, or when you use more than one AI app under one set of rules.
Side by side
| ChatGPT plugins | Keeploop | |
|---|---|---|
| iCloud Mail only (@icloud.com, @me.com or @mac.com addresses), connected with an Apple app-specific password. Other accounts in Mail, such as Gmail or Outlook, are not included. | Apple Mail on your Mac: every account you add to Mail and choose in Keeploop, including Gmail, Exchange, iCloud and other IMAP accounts. | |
| Calendar | iCloud Calendar: read, schedule and update events. | Calendar on your Mac: the calendars you choose, from every account it syncs. |
| Messages | The Apple Messages plugin searches, drafts and sends iMessage, SMS and RCS, in ChatGPT Work and Codex in the Mac desktop app. It does not work in regular ChatGPT chats. | Messages on your Mac, readable from any connected AI app, including ChatGPT on the web and phone. Sending texts is local only, never from a web or phone AI app. |
| Notes, Slack, Contacts | Not part of these plugins. The Mail plugin can look up iCloud contacts. | Notes, Slack and Contacts, each turned on separately. |
| Where it works | Mail and Calendar: web, desktop and iOS. Messages: the Mac desktop app, in Work and Codex. | ChatGPT on the web and phone through the ChatGPT app directory (Pro or the free trial), ChatGPT on the same Mac, and other AI apps such as Claude, Codex and Cursor. Your AI apps |
| Approvals | Sending a text needs your approval by default. | Block, Ask or Auto per AI app, account, label and contact. Ask waits for your approval on the Mac; the default for sending is Ask. |
| Price | Part of ChatGPT; the iCloud plugins are on every plan. | Free for AI apps on the same Mac. Pro is one purchase, not a subscription, for up to 3 Macs, with a 14-day free trial of every Pro feature, no card. Pricing |
| In the ChatGPT app directory | Built into ChatGPT, made by OpenAI. | Yes. Keeploop in the ChatGPT app directory. Setup |
Sources
Facts about other products come from their own pages or their makers' announcements, checked on October 28, 2026. Plans and features change; check the source before you decide. Keeploop facts: Pricing, Your AI apps, Security, Privacy.
- MacRumors: ChatGPT Can Now Access Your iCloud Mail and Calendar (checked October 28, 2026, published October 27, 2026)
- 9to5Mac: iCloud Mail and Calendar plugins now work with ChatGPT (published October 27, 2026)
- MacRumors: ChatGPT Can Now Read and Send iMessages on Mac (checked October 28, 2026, published August 20, 2026)