Big Sur - Issue opening any saved files by double-clicking

Yesterday I upgraded my MacBook Air (Early 2015, Processor 1.6 GHz Dual-Core Intel Core i5) to Big Sur 11.0.1. Initially everything worked perfectly fine. I was able to use all apps and files saved on my computer as well as on external storage devices.  I haven’t installed any other updates ever since nor installed any new software or downloaded any files from the internet. This morning, however, the system stopped functioning properly and I can’t open any files by double-clicking on them.Any time I want to open a file (.ppt, .pptx, .doc, .docx, .pdf and other extensions) with both third-party and native Apple apps, the system displays an error message and offers to move the files to trash (picture below). Control-> click -> open or rebooting the laptop and relaunching Finder doesn’t help.



I know for sure that the files aren’t corrupted for several reasons:


  1. Everything worked perfectly well yesterday
  2. Another MacBook Air 2015 running Catalina opens all files without any problems
  3. I can open the files from File -> Open... in the app menu Files tab
  4. I create and save new files to local storage, but when I try to open them by double-clicking, I get the same error message. 


This is SURreal that I can’t use the laptop’s primary function. How do I fix it ASAP without having to wait for the software update or rolling back to Catalina?



Thanks in advance for any tips and solutions!

MacBook Air 13″, macOS 11.0

Posted on Nov 13, 2020 3:56 PM

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Question marked as Top-ranking reply

Posted on Apr 7, 2021 11:08 AM

I encountered a similar problem to what is being reported here but involving shell scripts. I've got a Big Sur system that has been working fine since early Big Sur developer betas running scripts that build and package our products. For reasons as yet unknown several of our scripts began failing to run with the past few days. No macOS update as applied. Specifically, attempts to run them in terminal result in errors like this ...

zsh: operation not permitted: _scriptNameRedacted_


While other scripts in the same folder execute without any problem. Attempts to edit the affected scripts by drag-n-dropping the files onto BBEdit or TextEdit or Xcode resulted in the OS alert dialog others have posted pictures of; the alert with "filename is damaged and can't be opened. You should move it to the Trash".


Strangely enough though, I can 'vi' to edit and also manually open with BBEdit, TextEdit, Xcode those script files using the 'File > Open' dialog in each respective app. I just can't drag-n-drop those files without getting the damaged file alert dialog. This would appear to indicate that the Finder and some level of the file OS considers these files damaged even though they are accessible by other means and appear to be intact and fully human readable. (these files are shell scripts). This points to quarantining.


Sure enough, looking at extended attributes on the affected files with 'xattr _filename_' in the terminal shows this attribute on the affected files ...

'com.apple.quarantine'


I removed that attribute on affected files with ...

> xattr -d com.apple.quarantine _filename_


... and these scripts are now executable from the terminal, and can again be drag-n-dropped onto an text editor without encountering the damaged file OS alert.


You can search for quarantined files in a given directory by doing this in Terminal ...

> cd _target_folder_
> xattr * | grep "com.apple.quarantine"


I don't yet know why or what triggered the quarantine on some of my script files while others files in the same folder and on the same volume were not put in quarantine. I do not know if the files were put in quarantine by the OS or virus software or something else. (examining virus log files show my script directories getting scanned but no files/folders getting flagged as suspect and/or put in quarantine).


CAUTION / WARNING

Please be extremely careful removing the quarantine attribute on files on your system. DO NOT do something like run a script that removes the quarantine flag on all files on a system. You would be circumventing some of the file level security measures of macOS and putting the integrity of your entire system at risk. In my specific case above, I'm was working with affected shell script files which are text in content and are easily confirmed as human readable and intact before I pulled the files out of quarantine to allow them to be opened/executable again. If this works for you, great, but be VERY CAREFUL removing the quarantine attribute on files. Do it manually and carefully inspect each file one by one.


For non-textual files here is alternate possible solution for you. For each affected file, in the terminal ...

> cat _filename_ > _filename_2_


Then open the '_filename_2_' with the necessary application. If the new file opens and appears intact, close the file, delete the original file and rename your new file with the old filename.


If you use the 'cat' method to repair a file and that file is an executable script, you will need to add the executable bit to the new file.

> chmod +w _filename_2_


Also note that the above repair attempts will only work on uncompressed non-document bundle files. If you can select a file, right click on it and you see 'Show Package Contents', then that file is a document bundle. If you have something like a 'myProject.xcodeproj' Xcode project document that won't open, you will have to manually repair that document bundle hiearchy. When it comes to putting a document bundle in quarantine I don't know if the OS flags the top level hierarchy of the bundle or each individual file in the document bundle.

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Question marked as Top-ranking reply

Apr 7, 2021 11:08 AM in response to _-Ivan-_

I encountered a similar problem to what is being reported here but involving shell scripts. I've got a Big Sur system that has been working fine since early Big Sur developer betas running scripts that build and package our products. For reasons as yet unknown several of our scripts began failing to run with the past few days. No macOS update as applied. Specifically, attempts to run them in terminal result in errors like this ...

zsh: operation not permitted: _scriptNameRedacted_


While other scripts in the same folder execute without any problem. Attempts to edit the affected scripts by drag-n-dropping the files onto BBEdit or TextEdit or Xcode resulted in the OS alert dialog others have posted pictures of; the alert with "filename is damaged and can't be opened. You should move it to the Trash".


Strangely enough though, I can 'vi' to edit and also manually open with BBEdit, TextEdit, Xcode those script files using the 'File > Open' dialog in each respective app. I just can't drag-n-drop those files without getting the damaged file alert dialog. This would appear to indicate that the Finder and some level of the file OS considers these files damaged even though they are accessible by other means and appear to be intact and fully human readable. (these files are shell scripts). This points to quarantining.


Sure enough, looking at extended attributes on the affected files with 'xattr _filename_' in the terminal shows this attribute on the affected files ...

'com.apple.quarantine'


I removed that attribute on affected files with ...

> xattr -d com.apple.quarantine _filename_


... and these scripts are now executable from the terminal, and can again be drag-n-dropped onto an text editor without encountering the damaged file OS alert.


You can search for quarantined files in a given directory by doing this in Terminal ...

> cd _target_folder_
> xattr * | grep "com.apple.quarantine"


I don't yet know why or what triggered the quarantine on some of my script files while others files in the same folder and on the same volume were not put in quarantine. I do not know if the files were put in quarantine by the OS or virus software or something else. (examining virus log files show my script directories getting scanned but no files/folders getting flagged as suspect and/or put in quarantine).


CAUTION / WARNING

Please be extremely careful removing the quarantine attribute on files on your system. DO NOT do something like run a script that removes the quarantine flag on all files on a system. You would be circumventing some of the file level security measures of macOS and putting the integrity of your entire system at risk. In my specific case above, I'm was working with affected shell script files which are text in content and are easily confirmed as human readable and intact before I pulled the files out of quarantine to allow them to be opened/executable again. If this works for you, great, but be VERY CAREFUL removing the quarantine attribute on files. Do it manually and carefully inspect each file one by one.


For non-textual files here is alternate possible solution for you. For each affected file, in the terminal ...

> cat _filename_ > _filename_2_


Then open the '_filename_2_' with the necessary application. If the new file opens and appears intact, close the file, delete the original file and rename your new file with the old filename.


If you use the 'cat' method to repair a file and that file is an executable script, you will need to add the executable bit to the new file.

> chmod +w _filename_2_


Also note that the above repair attempts will only work on uncompressed non-document bundle files. If you can select a file, right click on it and you see 'Show Package Contents', then that file is a document bundle. If you have something like a 'myProject.xcodeproj' Xcode project document that won't open, you will have to manually repair that document bundle hiearchy. When it comes to putting a document bundle in quarantine I don't know if the OS flags the top level hierarchy of the bundle or each individual file in the document bundle.

Nov 14, 2020 9:46 AM in response to _-Ivan-_

Boot into Safe Mode (How to use safe mode on your Mac - Apple Support) 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


Also you might download and reapply the latest MS Office 2016 update again.

Jan 25, 2021 4:13 AM in response to The_joys_of_Apple

Quick update - I called Apple support. This was a printer issue. The update to my MS finally went through. But I had to remove my printer and then add it back in again (not the drivers) and that did a soft restart of my printer. the only catch is I have to open downloads from document finder, not in the document downloads in the bottom right corner. I’m hoping that will resolve with the next update. But at least a solution for now.

so - all a printer issue.

Nov 13, 2020 4:38 PM in response to _-Ivan-_

What version of Microsoft Office are you using?


Log into another vanilla admin user account, Set up users, guests, and groups on Mac and see if the problem persists. (This tells us if the problem is limited to your user account or is system wide).


Also boot into Safe Mode (How to use safe mode on your Mac - Apple Support) 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


Feb 24, 2021 9:38 PM in response to _-Ivan-_

I think I figured it out!


I had this problem with all my documents saved in Pages. After the Big Sur update, whenever I clicked on the documents that I'd saved to my iCloud Drive in the Pages format before I updated to Big Sur, it would say that the file couldn't be opened and might be damaged.


But I noticed that I could still use the Pages app. As in, the app itself wasn't damaged. Plus, I was able to open them on the Safari browser from my iCloud Drive.


And from my desktop, I could open my files with Word, TextEdit...anything but Pages. Even though the Pages app, once I re-downloaded it, would open! (Not sure why the app deleted in the update).


Then I realized that as long as I right-clicked on the document and clicked "open with Pages," I was able to open all the files easily.


But I didn't want to have to do that every time, obviously, so I just set all my files with the Pages extension to automatically open with Pages instead of TextEdit or Word.


You just right-click, hit "Get Info," and under "Open with" choose Pages.


Let me know if that helped!

Jan 22, 2021 12:54 AM in response to _-Ivan-_

I do also have the same issue on my Mac mini, but on my MacBook Pro where the same files on the same drive opens normally. The strange thing is that the problem occurs for example with pdf and doc -files, in Preview or Word. But, Adobe files and apps works as normal, so for instance I changed all pdf-files to open in Acrobat, and then they work fine. Unfortunately I don't have any alternatives to open Office-documents. Those I need to open thru the App using File -> Open.


At least in my case all files on the internal drive works normally, so this is basically an issue with external usb-drives.


Not the worlds biggest bug, but quite annoying.

Jan 5, 2021 11:07 AM in response to _-Ivan-_

I am getting the same problem, but I'm mostly noticing it on PDF files that are emailed to me and that I then download. I can often preview them with the space bar, but then if I either double click or click on "Open with Preview" in the preview window I get the "is damaged and can’t be opened. You should move it to the Trash." error. I'm currently on my 2nd reinstall of Big Sur, and it's still there.

Is there any way to just have it stop checking to see if it thinks the file is damaged and open it anyway?


Jan 22, 2021 7:04 AM in response to VikingOSX

My Big Sur and MS Office are both fully updated, but the double-click issue is still there. As long as I actually launch the relevant MS application first, I can open docs pp etc by double clicking. But if i haven't launched the application, double-clicking won't launch it as it used to. As bobi 151 said earlier "Not the worlds biggest bug, but quite annoying."

Mar 18, 2021 5:24 PM in response to Alisha2121

Yeah, in the end I had to downgrade as well. Even though I reinstalled Big Sur from a bootable usb and the files could be opened, but I couldn’t connect to the network printer, and some other apps that I frequently use didn’t work with with it. I can’t fathom why Apple would roll out such a useless upgrade like Big Sur.


I installed Catalina from a bootable USB as well. Everything is back to normal and I can now open all the files, though I never keep important files on the built in HD, only USBs or NAS.


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Big Sur - Issue opening any saved files by double-clicking

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