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I performed a fresh install of macOS Sierra onto a 2012 MBP13 non-Retina SSD. The install was from a USB flashdrive installer, and I set up the system drive partitions manually with a case-sensitive encrypted system volume, a FAT partition that I later installed Windows on, and a case-insensitive unencrypted volume for Steam data (Steam doesn't work for some reason, but that's another question!)

Partition map while MacOS is running:

aluminum:Downloads dhm$ diskutil list
/dev/disk0 (internal, physical):
   #:                       TYPE NAME                    SIZE       IDENTIFIER
   0:      GUID_partition_scheme                        *500.1 GB   disk0
   1:                        EFI EFI                     209.7 MB   disk0s1
   2:          Apple_CoreStorage Aluminum                319.8 GB   disk0s2
   3:                 Apple_Boot Recovery HD             650.0 MB   disk0s3
   4:       Microsoft Basic Data BOOTCAMP                146.3 GB   disk0s4
   5:                  Apple_HFS Steam                   32.9 GB    disk0s5

/dev/disk1 (internal, virtual):
   #:                       TYPE NAME                    SIZE       IDENTIFIER
   0:                  Apple_HFS Aluminum               +319.5 GB   disk1
                                 Logical Volume on disk0s2
                                 xxxxxxxx-xxxx-xxxx-xxxx-xxxxxxxxxxxx
                                 Unlocked Encrypted

During MacOS installation, I created a user account. Then afterward, I created two more. Now, when I reboot, I can choose MacOS or Windows (no recovery option). When I boot MacOS, I get a chooser that offers "Enter Disk Password," "User 2" and "User 3" (No choice to log into the account I made during installation.)

If I enter the disk password, then I get "User 1," "User 2" and "User 3," and everything works as expected. If I don't enter the disk password and just log in as "User 2" or "User 3," I get a desktop but things don't work right (lots of "Please fix the library" messages.)

My questions:

  • Why can I log in as "User 2" or "User 3" even without entering the disk password? (I would expect all the system-partition information to be encrypted, but it looks like there's at least some unencrypted information lying around.)

  • What's the difference between this setup and the alternative "Do a normal, unencrypted install, then turn on FileVault?"

  • Where can I read more about the various methods macOS uses to support multiple partitions, encrypted partitions, logical volumes & so forth?

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Not sure what the "please fix the library" message means but all of your data is encrypted on the boot partition. You can use a disk password, recovery key or allowed user passwords to unlock a FileVault disk.

When you do it the "normal way" as you mentioned above you won't end up with a disk password. No big deal.

It sounds like User 1 isn't allowed to unlock the disk in this case. You can use the fdesetup command for things like this. For example, to see which users are allowed to unlock the disk:

$ sudo fdesetup list
Password:
macmanager, 51361A22-B6F2-4384-8E0D-F4973BE74957

While logged in as any user you can look in System Preferences > Security & Privacy > FileVault and if some users aren't allowed to unlock the disk there will be a warning with a button to enable users.

You can also use fdesetup to add users to the list, assuming you know their password:

$ sudo fdesetup add -usertoadd davem
Enter a password for '/', or the recovery key:
Enter the password for the added user 'davem':

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