Catch-22: FileVault Encryption Complete, Can't Use Time Machine or Update OSX Because HD is Being Encrypted

Here is what I got. I don't see anything that mentions the filevault status and don't know enough to see anything else that seems relevant. This is a shared family desktop and not what I normally use (I didn't realize it was having this problem until the software updates stopped working). Fortunately, I've been able to copy the contents of the hard drive to a USB drive. I really appreciate your help, but unless you see something that I don't see, I'm thinking its time to erase and start over...

Now that I've wiped the disk and reinstalled Mojave, the backups are working fine.

In hindsight, what I could have benefited from was more information on how to prepare my files to make it easier to restore them on my computer. What I did was simply copy everything on the hard drive to an external USB drive.

I'm staying in Mojave because I think it will be easier to figure out how to fix anything that is broken if I don't add in the additional complexity and uncertainty of a different OS version.

Restoring my Contacts worked fine. Apparently I've been moving between Macs long enough that all I had to do was move a folder called Address Book as described in wanna save contacts on my old macbook - Apple Community. However, as discussed in this link, this might not work for everyone.

Multiple postings indicated I should be able to move Mail over by moving three files, the Mail Folder, Mail Preferences, and KeyChain. This did not work for me. I ended importing my old messages into Mail (using File/Import Mailboxes) from user Library/Mail folder. After the import, all the data is there in an "Import" mail folder, but former large mailboxes are broken up into smaller mailboxes, often with the same name but in different subfolders, so it took some time to make sense of and rearrange the imported mailboxes. In hindsight, it may have made sense to have exported all of my mail before I wiped the drive, so that the import would have been cleaner (but since I didn't try this, I'm not sure how well this would have worked)

My first attempt to restore my iTunes did not work. My recollection from years ago was that all I needed to do was move the iTunes folder into the Music folder. I tried this, but although all playlists were there and the song titles listed, the links are broken so when you try to play something, it asks you to help it find the file (probably an XML link problem). If I go into iTunes Preferences/Advanced and change the iTunes Media folder location to the backup iTunes folder on the USB drive, iTunes works fine. I'm going to do a little more research, but I think what I need to do is export my iTunes library, then import it into iTunes on my restored drive.

I'd already set up Photos to use an external USB drive, so I don't anticipate a problem with Photos, but...

Whenever possible, I plan to do a fresh install of any software. Unfortunately, Apple apps like Pages on the App Store all require MacOS 11 or higher, so I'll hold off on this until I've fixed any problems with Contacts, Mail, Music, Photos, etc., then update to Monterey to restore these apps.

I'm hoping that posting information and suggestions about what to do if you can't use Time Machine or Migration Assistant to backup and restore a hard drive might be useful to others in this situation.

my ginger, thanks for the response. As I explained in the original post, no progress bar, no indication that encryption is not complete (on a few occasions a progress bar may appear, apparently when there is new content to encrypt, but it completes in a few minutes). I have also checked in terminal mode. This has been going on for well over a year...

BDAqua, thanks for the response. APFS rather than CS, but no indication that any conversion is in progress:

APFS Container (1 found)

|

+-- Container disk2 8BE1A52C-92D5-46F3-B211-A865AC6E8045

====================================================

APFS Container Reference: disk2 (Fusion)

Size (Capacity Ceiling): 2121312247808 B (2.1 TB)

Capacity In Use By Volumes: 1988907266048 B (2.0 TB) (93.8% used)

Capacity Not Allocated: 132404981760 B (132.4 GB) (6.2% free)

|

+-< Physical Store disk0s2 E2DC4808-27F1-48FC-9685-1F7ED3B75AFC

| -----------------------------------------------------------

| APFS Physical Store Disk: disk0s2 (Main)

| Size: 121123069952 B (121.1 GB)

|

+-< Physical Store disk1s2 D5AB9F6F-5F05-4BD2-AFE3-9426F978AD10

| -----------------------------------------------------------

| APFS Physical Store Disk: disk1s2 (Secondary, Designated Aux Use)

| Size: 2000189177856 B (2.0 TB)

|

+-> Volume disk2s1 A1136F0A-4B0F-3CBC-99C8-12293116E6A9

| ---------------------------------------------------

| APFS Volume Disk (Role): disk2s1 (No specific role)

| Name: Macintosh HD (Case-insensitive)

| Mount Point: /

| Capacity Consumed: 1977177042944 B (2.0 TB)

| FileVault: Yes (Unlocked)

|

+-> Volume disk2s2 9798BDDC-D96C-43C5-ABBF-E1BCEB51C460

| ---------------------------------------------------

| APFS Volume Disk (Role): disk2s2 (Preboot)

| Name: Preboot (Case-insensitive)

| Mount Point: Not Mounted

| Capacity Consumed: 114860032 B (114.9 MB)

| FileVault: No

|

+-> Volume disk2s3 1BBAE9F7-FCF3-49A0-9CA9-8DE587F6300B

| ---------------------------------------------------

| APFS Volume Disk (Role): disk2s3 (Recovery)

| Name: Recovery (Case-insensitive)

| Mount Point: Not Mounted

| Capacity Consumed: 510566400 B (510.6 MB)

| FileVault: No

|

+-> Volume disk2s4 94B0E402-392B-417D-982B-6A8B80CE598D

---------------------------------------------------

APFS Volume Disk (Role): disk2s4 (VM)

Name: VM (Case-insensitive)

Mount Point: /private/var/vm

Capacity Consumed: 2149060608 B (2.1 GB)

FileVault: No

my ginger, thanks! I'm just about ready to erase the disk and start over, but thought I'd go out and check with others, in case there is something I have missed. It may be as simple as the encryption has completed but some flag has not gotten updated, but if so, I don't know where it is or how to correct it...

my ginger, thanks again! This was promising but did not work in my case (but might be helpful for others encountering this).

I followed the FileVault login screen password reset option in the link you sent, and the results were at first promising. System Preferences/Security & Privacy/FileVault showed encryption in progress with 2 hours left, then shortly after that showed encryption complete. However, at that point the option to turn of FileVault was still greyed out, Time Machine backups were still not working because the Time Machine thinks the disk is still being encrypted, and I was unable to reinsall OSX on the HD because the disk was still being encrypted.

So I decided to try following the macOS Recovery password reset option in the link you set. I first went into Terminal mode and got a "false" response (for both of my login accounts) to both "sudo fdesetup haspersonalrecoverykey" and "sudo fdesetup hasinstitutionalrecoverykey" so my HD apparently did not have a FileVault recovery key set. Just to be sure I tried "sudo fdesetup enable" and got "Error: FileVault is already On." I then used "sudo fdesetup changerecovery -personal" to create recovery keys for both user accounts, then tried to follow the instructions. It did quite work out as described, in that the resetFileVaultpassword utility did not ask for a recovery key, but instead used my Apple account. To see if this was because I was online, I tried without the internet connection and was unable to use this utility.

So, I have reset my passwords, it did appear to cause the system to realize that encryption was complete, but it did not persist long enough to solve the problem.

Interesting! I'm not sure if it means the same thing, but Secure Token is enabled for the only two User accounts.

Mac-mini-2:~ gordonjohnston$ sysadminctl -secureTokenStatus gordonjohnston

2022-03-27 08:16:36.227 sysadminctl[2227:24423] Secure token is ENABLED for user Gordon Johnston

Mac-mini-2:~ gordonjohnston$ sysadminctl -secureTokenStatus worker

2022-03-27 08:17:03.256 sysadminctl[2228:24604] Secure token is ENABLED for user Worker

Mac-mini-2:~ gordonjohnston$

Although I've learned more about how Macs work, at this point I'm not sure what to do about either, other than erase and start over...

Thanks again for trying to help!

I do have an operating system on an external USB drive. After the Monterey update crashed my machine and left me unable to boot up, I formatted and put OSX on a USB drive so I could boot up and copy all of my data off the hard drive. I did this before I tried anything else to preserve my data.

I followed the instructions from the link you sent, but had to modify them some. According to https://derflounder.wordpress.com/2017/12/31/decrypting-an-apfs-encrypted-volume-using-diskutil-on-macos-10-13-2/ after 10.13.2 the appropriate user UUID is needed. I tried both disableFileVault and decryptVolume and got "Error starting background decryption of APFS Volume: APFS Volume decryption failed to begin (-69595)"

While I enjoy a good puzzle when I have the time to work on it, I am proceeding with a full up erase and reinstall on the Hard Drive.

Thanks again, I at least learned more about OSX!