M1 System Extension Cache Rebuilding Loop

had the same issue on Big Sur 11.2 but now on the loop issue is fixed in 11.3 beta version and it works

Hey guys, after A LOT of digging, I finally found a solution and wanted to share it here to save everyone the headache. Here’s what I did:

1. Open Terminal 

2. Run the following commands:

• sudo rm -rf /Library/Extensions/dfsfuse.kext 
• sudo kmutil clear-staging

3. Shutdown the computer 
4. Restart the computer in recovery mode by holding down the power button until Loading startup options appears
5. Click Option and then Continue 
6. Click Utilities > Terminal 
7. Run kmutil trigger-panic-medic -- volume-root /Volumes/Macintosh \ HD
8. Confirm that the output from this command indicates that kernel extensions have been removed
9. Proceed with Step 3, including reboot

Once I started back up, I hit allow, restarted once more, and Google Drive worked perfectly

I'm having a similar issue after reboot with Google Drive permission loop. After rebooting several times, I can finally use Google Drive. I uncheck the “reopen windows when logging back in” when restart.

My Issue
I was having a similar issue when installing Google Drive. In the Security/Privacy panel, it would tell me the extension had been updated and that I needed to restart, giving me the option to click 'restart' or 'not now.' Whenever I clicked restart, it would restart the loop.

What Worked For Me
I clicked 'Not Now' and restarted on my own. When it restarted this time, the extension was properly installed with no prompt to restart.

Hopefully this helps!

I was having the same issue with Google Drive. The solution posted by ahelpfuluser worked for me https://developer.apple.com/forums/thread/667739?answerId=670780022#670780022

Solution from this post https://developer.apple.com/forums/thread/667739?answerId=670780022#670780022
unfortunately did not work for me.

EDIT:
Solution: Install new version (47)

dl.google.com/drive-file-stream/beta47/GoogleDrive.dmg

Worked well.

https://developer.apple.com/forums/thread/667739?answerId=670780022#670780022
Worked for me.
At the end it says "9. Proceed with Step 3, including reboot", but there is no step 3 so I did a

• 'reboot' from the terminal and

• once booted did an install from a freshly downloaded "GoogleDrive.dmg" (was version 47.0.17.0).

• Then approved the extension in the preferences.

• Chose "Not now" for the reboot.

• Closed Preferences.

• Rebooted from the Apple menu.

Thanks,
Solution This worked for me !

Just careful at step 7 the command is : kmutil trigger-panic-medic --volume-root /Volumes/Macintosh \ HD
with no space between -- and volume.

I've had a similar problem installing the latest version of WD desktop application on Big Sur M1. It kept endlessly looping between restart and approve security. started regretting the WD upgrade. Finally, the problem Resolved immediately after updating to Monterey.

Another non-answer: same problem still on upgrading to Monterey 12.3.1 (21E258) — in my case Seagate Technologies. That's external drive management. My view is that Monterey/M1 Silicon is a technology still in development, patchy, lacking some old functions, introducing problems, and compounded by developers not keeping up, partly because it is still a small part of the stable. Apple needs real investment. Since going to M1 there has been nothing but a series of problems and with big names like Microsoft.

I had this problem with Segate. First I ran it 3 times and that fixed it. Maybe for now anyway. I also found this on their website, which avoids using Terminal. https://www.lacie.com/gb/en/support/kb/how-to-change-startup-disk-security-settings-on-an-apple-silicon-mac/

• 1. Some Seagate and LaCie software use a kernel extension (kext). Apple silicon Macs require that users change the security settings to ‘Reduced Security’ for the software to function properly.
• 1. To change the level of security on your startup disk:
• 1. Shut down the Mac
• 1. Press and hold the power button until you see “Loading startup options”
• 1. Click Options
• 1. Click Continue
• 1. If asked, select a user > Click Next > Enter password for admin account
• 1. In the menu bar at the top, Select Utilities > Startup Security Utility
• 1. Select the startup disk
• 1. If the disk is encrypted, Click Unlock > Enter Password > Click Unlock
• 1. Click Security Policy
• 1. Select Reduced Security
• 1. Put a check next to “Allow user management of kernel extensions from identified developers”
• 1. Click OK
• 1. Enter admin password > click OK
• 1. Once changes are applied, click the Apple icon and Restart