Troubleshooting iCloud on Mac

Earlier this year I set up a new user on the family iMac, but Pages, Numbers, and Keynote occasionally gave me trouble when working with iCloud. The symptoms:

Today I decided to figure out the problem once and for all, and I’m posting this here as a shout-out to the people who helped me and for anyone else who might encounter the same problem in the future.

For the record, my software versions were:

Troubleshooting

Internet searches and forums yielded multiple potential solutions, but none of them solved my problem. I tried various forms of turning it off and back on again including:

  1. Disabling iCloud Drive in System Preferences
  2. Signing out of iCloud in System Preferences
  3. 1 and 2 with the addition of logging out and back in before re-enabling iCloud Drive
  4. 3 with the addition of rebooting

None had any effect on the behavior, so I decided to call for help1. I’ll just put it out there that Apple has great and friendly phone support!

We isolated the problem to that single computer since I could open the files on icloud.com and none of my other devices exhibited the problem. We found that I could create new files and upload them to iCloud, but once closed they could not be opened again. I also noticed that even though I had 500+ MB of data stored in iCloud, my usage showed 4.99 GB free of 5 GB available. I had not noticed that before.

When I offer technical support for friends and family, seeing the screen and witnessing the problem firsthand can be very helpful. This was no different, so I opened a screen-sharing session with Apple to help diagnose the problem. Eventually, we further isolated the problem to my user: I was able to open iCloud documents under a newly-created user.

Solution

Once we determined that something was wrong with my user configuration, we made sure my user had access to all files:

  1. Activate Finder
  2. Go > Home (command + shift + H)
  3. File > Get Info (command + I)
  4. under Sharing & Permissions ensure that files are readable and writable by your user
  5. under the other actions drop-down (the button with the gear and down chevron) click Apply to enclosed items…

This did not solve the problem, but it ensured that the next set of actions would work. Deleting the following items solved the problem for me:

Closing Remarks

A big thank you to Donna, Jessica, Chris, and Chris for helping me diagnose and solve this problem! If any of you find your way to this post, here are some links to some other topics we discussed:

  1. My friends and family usually call me for technical support, so I usually feel a sense of irony whenever I call technical support. ↩︎

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