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Mike TewFlag for Canada

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How do I fix file "... is damaged and can't be opened. You should move it to the Trash." in Monterey OS?

I need to fix the Mac MontereyOS issue with file download. I keep getting the file "... is damaged and can't be opened. You should move it to the Trash." Currently, the only workaround is using the "xattr -cr " command and then dragging the file into Terminal. I tried temporarily disabling gatekeeper, but this still required me to run the command in Terminal.


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I wonder if this results from upgrading from a MacBook Pro 2013 (Catalina OS) to a newer 2015 with (Monterey) installed and restoring from my Time Machine backup.

Initially, the 2015 MacBook Pro had Monterey pre-installed. However the restore failed, and I was then forced to do a factory reset on the 2015; this put the OS back to El Capitan. Time Machine restored successfully here, but there was an issue with duplicate admin "user" accounts during the process, so the restore created "user 2" as the admin.

After that, I ran the software update and reinstalled Monterey via Software Update, which brought me to where I'm now.

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Jackie Man
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Are you using MacBook Pro 2013 or 2015?

If it is 2013, it is not compatible with the new Monterey MacOS.
How you download the file?
Context... a starting point is required...

1) Provide full path to the file, including the extension.

2) Provide the output of file /path-to-your-file, which should match the extension from #1.

Note: If #1 != #2, simple fix is to rename file with correct extension.

3) If #1 + #2 seem correct, then describe file's history.

As @omararid suggested, mention source of the file, so downloaded, created by you, how file came to exist.

Looks like a Firefox download, so provide the download URL of the file for testing, because if file is corrupt at source (download URL), it's unlikely you can ever repair the file.

Note: Usually when this occurs a file is downloaded with no extension, so the file is correct... with a bare/missing extension... so MacOS becomes confused about how to open the file.

4) Then mention how you think file became corrupted.

5) If you get completely stumped, attach the file to this question for testing, or if the file is to large, place the file on a Webserver somewhere + provide the URL of the file.
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ASKER

Hi David,

Thank you for the feedback. I'm completely stumped on this one. I think it's an issue generated from the Time Machine restore. Specifically with the Monterey settings or a permission issue going from Catalina (2013 MacBook Pro) to Monterey on the 2015 MacBook Pro.

Any file I download generates the message, pdf, png, jpg, docx, xlsx, etc.
I've downloaded from Firefox, Chrome, Spark (email client), they all do this. So far, the only solution I can do is the terminal command, which is not the best for workflow.

Anything preexisting from the time machine restore opens no problem. Here are some files I have downloaded today that all generate the Monterey OS message

Via Firefox / Adobe Stock
AdobeStock_254111239-1.ai

Via Spark (email client); embedded in an email
apple-icon.png

Via Chrome from amazon.ca
4139IcurSZL._SY90_.jpg

Via Chrome / gmail; I renamed the file but kept the extension
instacart.png

Via Firefox / office.com - Sales Tracker template https://templates.office.com/en-ca/online-sales-tracker-tm10000095
tf10000095.xlsx

Via Chrome / office.com - Resume template https://templates.office.com/en-us/modern-chronological-resume-tm16402488 I saved this to my desktop instead of downloads folder
tf16402488_win32.dotx

Hi Jackie,
My old machine 2013 is Catalina, my new one is a 2015 w/ Monterey.

Thanks
Hey David,
Just another note. On both machines, I cannot verify the time machine backups. Could they be corrupted?

The 2013 is almost unusable as the SSD is dying. I did complete a successful backup before this was really bad. However, I'm considering rolling back to even further Time Machine backup in case the last version is corrupt.
My wild guess is that there are disk permission issues from the restore of your Time Machine backup. The general principle of data recovery is rubbish in and rubbish out as backup from a dying disk is not reliable.

https://macpaw.com/cleanmymac

You need to redo the factory reset of your new MacBook. Then, do a restore from Time Machine backup and run the above app to fix disk permission problem before you try to do OS update to Monterey OS.
Thanks Jackie,
I originally did this because the restore in Monterey failed. After the factory reset to El Capitan (2015 MacBook) the time machine restore worked. However, I skipped the disk permission check and went straight to upgrading Monterey. If I'm not able to fix the permission issue with Monterey now installed, I will redo the factory reset.


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Mike Tew
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