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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4 replies

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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