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I wanted to upgrade from Big Sur to Monterey and after the download completed, I get this message, that I cannot upgrade because my disk was encrypted.

enter image description here

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  • How did you encrypt this disk in the first place? If you're already logged in as the admin user, then the disk should be unlocked.
    – benwiggy
    Commented Oct 28, 2021 at 8:50
  • While installing Mac OSX a year ago approx. The disk is the first thing I have to unlock while booting any further to the login screen, so both should be unlocked by now
    – Horsty
    Commented Oct 28, 2021 at 9:19

2 Answers 2

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I got it working in the end! Coming from another bug I got the following solution steps, in order to get it working.

Warning in FileVault

As you can see here in FileVault, there was a warning displayed, that were some users not being able to unlock the disk. The button "Enable users..." in addition to the button "Turn Off FileVault" were not clickable, so I troubeshooted that problem with this and came to this Reddit thread. The second answer from the first post was also needed to troubleshoot and fix the bug.

Short summary / tl;dr

  1. Identify if your current or any user has Secure Token enabled with

    sudo sysadminctl -secureTokenStatus <usr>

  2. Check every user on your system

  • 2.1 Search for users

    dscl . list /Users | grep -v '^_'

  • 2.2 Check the user with

    sudo sysadminctl -secureTokenStatus <user>

  1. If for every user the return is Secure token is DISABLED for user <user>

    sudo rm /var/db/.AppleSetupDone

    for reenabling the Apple Setup Page

    and reboot normally

  • 3.1 Setup a new user in the setup menu

    This user will have the Secure Token ENABLED

  • 3.2 Go to Users & Groups and reset the other account's password

    The old user will now have his Secure Token ENABLED (again / reenabled)

  • 3.3 Log out with the current (temporary) user

  • 3.4 Log in with the old user

  1. Check the update page again and update to Monterey The error should be gonegone
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  • 1
    Thank you so much this was 100% the solution I needed. I had set up FileVault when I originally installed MacOS a few versions before Monterey. After setting up the secondary Admin account I was able to reset the password for the original account and install without issues after that without having to disable FileVault.
    – rockhowse
    Commented Dec 6, 2021 at 3:49
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Same here, as interim solution i would try

  • booting into rescue mode,
  • deactivate DISK AES Encryption
  • normal boot and install
  • back to recovery and reactivate AES Encryption
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  • Sounds like a dirty hack, but will do so if there is no other way. Thanks
    – Horsty
    Commented Oct 28, 2021 at 8:17
  • I don’t believe it is possible to use Disk Utility to remove encryption from a drive (in-place) when the entire disk is encrypted with a disk password (as opposed to the more commonplace user-level filevault situation). (Maybe with an external drive as an interim store for the disk contents, but not in one step and not without extra storage devices.)
    – Alan H.
    Commented Nov 7, 2021 at 21:00

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