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I've recently updated to High Sierra and am now having issues with the encryption of my SSD.

When upgrading I was prompted to create a new password for my user account, the dialog saying that I couldn't use the same password as my iCloud account anymore. This led to when I restarted my MacBook Pro, I had to log in twice. Once for the disk encryption, and one for the user account. This wasn't ideal for me, so I contacted Apple support to ask about the issue. They were only able to help me roll back to a previous Time Machine backup from before I updated, so now I'm running Sierra again.

I suspect the option to use your iCloud password in conjunction with your user account (and other things...?? FileVault?) is what has caused the issue. Now that I'm up and running again on Sierra 10.12.6, I don't even see it as an option when I go to system preferences.

My question is, what is the best way for me to proceed to:

  1. Have an encrypted SSD
  2. Run the latest version of macOS (High Sierra)
  3. Have as few passwords as possible (though I can use 1Password to store them if I need many separate passwords, it's just more messy.)
  • Have you tried changing your Apple ID/iCloud password? – oa- Oct 9 '17 at 8:35
  • No I haven't at this point. What would that do to remedy things? – CodyN Oct 9 '17 at 9:02
  • In your question you said "the dialog saying that I couldn't use the same password as my iCloud account anymore." I guess that changing your password will let you prevent this message. – oa- Oct 9 '17 at 9:21
  • This dialog appears in the middle of the OS upgrade (or when I've reinstalled Mac OS, so there's no way to really go change it and then come back since it's in the of the upgrade process. – CodyN Oct 9 '17 at 9:54
  • Can't you change your iCloud password before you start the upgrade? – fsb Oct 9 '17 at 11:59
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If you have an encrypted drive before installing the OS you get that multiple login issue. If you do an install on a standard drive, then turn FileVault on, you won't have to double log in, as the user login will 'decrypt' the drive on its own.

I believe that's what solved a similar issue for me. I did a second clean install, this time formatting APFS (without encryption).

  • i upgraded my encrypted drive from Sierra to High Sierra and doesn't get multiple login issue. Maybe Apple fixed it. Hope it helps – Nicholas Ng Dec 26 '17 at 23:06
  • @NicholasNg : what kind of disk do you have (SSD or RHD)? Which is the format of your MacOS partition (HFS+ or APFS)? – dan Apr 29 '18 at 14:49
  • @danielAzuelos Stock SSD and APFS. Apple converted to APFS automatically – Nicholas Ng May 2 '18 at 1:52

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