"filename" is damaged and can't be opened. You should move it to the Trash.

I recently moved my files to a new installation on an older (2014 MacBook Pro) and updated to MacOs 11.2.1. When I double click on a .jpg or .pdf file on my desktop the first time, it opens right up in Preview. When I click on it again, I get:" 'filename.jpeg' is damaged and can't be opened. You should move it to the Trash. Preview created this file yesterday at 8:30 PM."

  • The time mentioned above is the time that I opened the file the first time when it opened ok.
  • If I open Preview and then navigate to the same file from within Preview, it will open the file.
  • If I right click on the file and select "Open With" and select Chrome, I get the same message.
  • If I open Chrome and then click File, Open I can navigate to the file and it will open.
  • If I right click on a "damaged" file and select "Quick View", it opens without a problem.
  • Starting up in Safe Mode does not change the behavior.
  • If I go into time machine and restore the file back to the time just after the update, it will open normally, then it will go back to the same behavior.
  • I did a restore of MacOS 11.2.1. No change.
  • I attempted to do a fresh install of Chrome. When I downloaded the dmg file and tried to open it from the downloads folder, it causes the same message. "googlechrome.dmg is damaged . . ." Now I can't run Chrome.


MacBook Pro 15″, macOS 11.2

Posted on Feb 17, 2021 7:04 PM

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12 replies

Feb 17, 2021 8:13 PM in response to Balloonatick

The problem that you are running into is that Gatekeeper is trying to protect you from malware and not only doesn't recognize the developer "signature" of the App you downloaded it "sees" the file was modified by someone/something other than the developer.


Gatekeeper options are found in Apple menu > System Preferences… > Security & Privacy > General tab.

Are you able to go there and hit allow anyway after getting the "move to trash" warning message?

Feb 18, 2021 11:42 AM in response to Balloonatick

Boot into Safe Mode by booting with the Shift key held down and check there to see if the problem persists.  Reboot normally and test again.


NOTE: Safe Mode boot can take up to 10 minutes as it's doing the following; 

• Verifies your startup disk and attempts to repair directory issues, if needed

• Loads only required kernel extensions (prevents 3rd party kernel/extensions from loading)

• Prevents Startup Items and Login Items from opening automatically

• Disables user-installed fonts 

• Deletes font caches, kernel cache, and other system cache files


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"filename" is damaged and can't be opened. You should move it to the Trash.

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