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Reply to M1 System Extension Cache Rebuilding Loop
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!
Apr ’21