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Ever since I upgraded to Catalina, I've had a problem where the files within the Pages and Numbers folders in iCLoud don't sync to my Mac, except for files I've created since the upgrade. However, if I go to iCloud.com I can see everything. I have tried:

  1. Turning iCloud on and off again
  2. Re-installing Catalina
  3. Uninstalling Pages and Numbers (properly, with AppCleaner)

Here are my system specs System specs I'll add any more info if needed.

  • Are your iOS devices up to date? – Chris Nov 15 '19 at 20:03
  • I don't have any – Southpaw1496 Nov 16 '19 at 12:31
  • Ah ok. I’ve had this problem when using different versions of the Mac and iOS apps. – Chris Nov 16 '19 at 12:36
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I managed to do it by signing completely out of iCloud and signing back in.

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