Cannot Delete File From Desktop

Hello! My laptop updated to Sonoma14.1.1 and when it restarted, it had pulled 8 random files out of my trash. Ever since, they have had a cloud symbol with an ! next to them (pictured), and it won't let me delete them off of my desktop. When I try to delete them, it asks for my password like normal, but then a window pops up that says, "The operation can’t be completed because “docs” needs to be downloaded." (pictured)


Things I have tried:

  • Restarting my computer.
  • Going to icloud.com and deleting them on there. This did delete them on iCloud, but did not solve the desktop issue.
  • Right-clicking the files and selecting "remove download." This will make the cloud symbol disappear maybe half of the time, but when I try to delete the file, the window pops back up, and eventually, the cloud returns.


Does anybody have any possible solutions? They're in my way!


MacBook Pro 13″, macOS 14.1

Posted on Nov 29, 2023 11:05 AM

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Question marked as Top-ranking reply

Posted on Jun 1, 2024 7:27 PM

I had exactly the same problem, and I solved it!


On a whim, I selected the offending file, entered "command-I" to get info, expanded "Permissions" and clicked on the little lock icon in the bottom right corner. I selected "Read/Write" and changed it to "everybody." Then moved the file to the Trash and emptied. Worked like a charm!

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4 replies
Question marked as Top-ranking reply

Jun 1, 2024 7:27 PM in response to tgarn

I had exactly the same problem, and I solved it!


On a whim, I selected the offending file, entered "command-I" to get info, expanded "Permissions" and clicked on the little lock icon in the bottom right corner. I selected "Read/Write" and changed it to "everybody." Then moved the file to the Trash and emptied. Worked like a charm!

Nov 29, 2023 12:26 PM in response to tgarn

tgarn wrote:

• Hello! My laptop updated to Sonoma14.1.1 and when it restarted, it had pulled 8 random files out of my trash. Ever since, they have had a cloud symbol with an ! next to them (pictured), and it won't let me delete them off of my desktop. When I try to delete them, it asks for my password like normal, but then a window pops up that says, "The operation can’t be completed because “docs” needs to be downloaded." (pictured)

Things I have tried:
Restarting my computer.
• Going to icloud.com and deleting them on there. This did delete them on iCloud, but did not solve the desktop issue.
• Right-clicking the files and selecting "remove download." This will make the cloud symbol disappear maybe half of the time, but when I try to delete the file, the window pops back up, and eventually, the cloud returns.

Does anybody have any possible solutions? They're in my way!


https://discussions.apple.com/content/attachment/e251834e-2d25-423a-8d98-cae7113b2835
https://discussions.apple.com/content/attachment/d32db789-333a-427e-96b1-afc1a91f2423


—A SafeBoot Use safe mode on your Mac - Apple Support will sort many anomalies

login and test, reboot as normal and compare your results.


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Cannot Delete File From Desktop

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