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Clean Install Problems With Encrypted Time Machine

I recently upgraded to Mavericks. My MacBook Pro was a bit sluggish so I decided I would do a clean install on both my machine and my wife’s MacBook Pro. I followed the instructions and made a bootable USB drive with Mavericks. I backed up my wife’s computer using Time Machine. I booted from the USB drive, used disk utility to erase her hard drive and then installed Mavericks. As I was proceeding through setup I attached the Time Machine and everything worked absolutely perfectly. Her computer zipped along with the clean install.


I then went to work on mine. I made two encrypted Time Machine backups (2 separate external hard drives). I then booted from the USB drive, used disk utility to erase my hard drive and installed Mavericks. THE PROBLEM: during setup I attached my Time Machine backup and proceeded. However, my MacBook Pro could not find my Time Machine. I tried this a few times, no luck. I then tried it with my other Time Machine backup. Still no luck.


I ultimately created a user and then tried Migration Assistant. Once again it could not find my Time Machine backup. Finally, I despaired, restarted my computer with Command R and selected restore from Time Machine Backup. This time my MacBook Pro immediately recognized my backup, asked for the encryption password and restored my machine.


The only difference between my wife’s Time Machine and my Time Machine is that mine are encrypted.


Any ideas about why I could not do either a clean install and transfer information using Time Machine OR use Migration Assistant? Thanks!

MacBook Pro (13-inch Late 2011), OS X Mountain Lion (10.8.2), Processor 2.4 GHz Intel Core i5,

Posted on Nov 4, 2013 5:45 PM

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15 replies

Nov 4, 2013 6:57 PM in response to Mark2006

I'm not sure if we had the same issue but my problems with a Mavericks upgrade were possibly related to having FileVault 2 active and encryption on. If possible, turn off those before trying to install.


If you are caught in a loop saying your disk is damaged, this post from another thread helped me get past that loop. I had to resize the partition of the HD slightly and then all went smoothly after that. Hope this helps and let us know.


https://discussions.apple.com/thread/5507734

Nov 5, 2013 8:57 AM in response to Mark2006

Since upgading to mavericks migration assistant no longer sees my backup on my external drive that I use for my time machine backups. The drive mounts fine and I can access my backups through my finder using "enter time machine", but I can not restore because migration assistant can't see the drive. I don't knoe if it's a time machine issue or a mighration assistant issue. I have tried on several macs and with several different hard drives but migration assistant cannot restore from my time machine backups. I suggest everyone make sure they can restore from their time machine backups because this may be a major problem and result in complete loss of data. I have found no solution yet.

Nov 7, 2013 3:21 AM in response to Mark2006

Hi, Mark. As I set up ML roughly a year ago I had a similar problem: the Migration Assistant during the OSX setup couldn't find the TM volume (which made me think that the disk was gone). As far as I remember I found the solution by clicking somewhere (sorry, don't remember exactly where) on the menu bar and selecting something like "unlock Time Machine disk" or whatever label it may have.


You may pre-test this tip by restarting a Mac (maybe your wife's), pressing cmd+R to enter the revery mode and then, after connecting an encrypted disk, start Utility Disk and unlock it. You'll be prompted to enter the password, afterwards the disk works fine, like it wouldn't be encrypted.


Again: I don't remember well how it works in Migration Assistant (I'm not a Pro!), but I did it in a similar way, so it shouldn't be impossibile for noone.


Hope this helps!

Nov 17, 2013 1:27 PM in response to Mark2006

It looks like I have to apologize: I recently clean installed a copy of Mavericks and I stumbled in the same issue of yours. The "trick" I described works only when booting from the recovery partition.

It's kind of an omission on Apple engineers' part. I hope they'll fix it, since Craig Federighi encouraged Mac users to use File Vault 2 back at the time when it was introduced.

Feb 8, 2014 12:33 PM in response to Mark2006

I have this same problem - I think - let me clarify: restoring from an encrypted time machine backup via command-R at boot finds my time capsule and the encrypted backup and can access it. I can not at this time confirm that a complete restore would be successful via this route (will explain). Data migration assistant however can not "see" an encrypted time machine backup sparsebundle. The reasons why are not clear, but even though it may find your time capsule or other system on the network, it won't find an encrypted TM backup. One can not restore data and applications via the data migration assistant in 10.9.1 if the time machine backup is encrypted. From my research on this so far, this problem may not be limited to OS X Mavericks and may have been a problem before as well.


My macbook pro (mid 2012 series) recently died and needs a logic board replacement. I have a loaner system while waiting the week or so it will take, but it has been useless so far because the loaner system is a newer model MacBookPro than mine and command-R won't do a restore from time machine backup due to hardware incompatibility. The correct choice should be data migration assistant, treating this loaner system as if I had purchased a new model. However, as explained above and by others, it can not find or "see" encrypted time machine sparsebundle disk images. Those same sparse bundles can be mounted and accessed within the Finder in OS X itself though, provided you know the encryption password of course.


I can not find instructions anywhere for *removing* the encryption from the sparse bundle disk image. That is my main question at this point. The only option (trying now - waiting hours for copying to take place) I can think of is to first create a copy of the TM backup sparse bundle so I don't mess directly with what is my only full backup, mount it in the Finder or via diskutil or hdiutil or whatever, create a new sparse bundle w/o encryption, then wholesale copy the entire contents to the new sparse bundle that never had encryption turned on. The question then will be whether or not data migration assistant will recognize it still as a time machine backup or whether there are hidden aspects of the image/volume/bundle/whatever that won't be propogated by either a drag and drop copy or a command line copy. A second option which I will try first (still trying to create a working copy) is changing the password (hdiutil chpass) to an empty password. I don't know if this will remove encryption completely such that DMA will then recognize the sparse bundle, or whether it will still be encrypted and inaccessible to DMA, but with no real security due to the password now being blank. DMA doesn't show the encrypted backups but fail accessing them even when the correct passwords are supplied, it doesn't show them at all - causing a bit of nervousness because it looks like there are no backups there at all.


This is a serious bug in Data Migration Assistant. If my hardware comes back with the same model logic board and not an upgraded but compable board (quite possible 2 years out now), then presumably command-R will put me back in business if during the repair process my files on the HD are lost or damaged. If not though, unless I figure this out, the time machine backups are useless.

Feb 8, 2014 3:52 PM in response to slowkoni

Thanks for the thorough discussion of your experience. I am eager to hear what happens when you try the various possible solutions. And I agree, this is a very serious bug in DMA. Ultimately what I did, which unfortunately is not available to you at this point, was to boot to disk utility, erase my hard drive, then use command-R to restore from my encrypted time machine. At this point I no longer had a clean install making all the previous efforts null and void. I then made an unencrypted time machine backup, did the clean install and used DMA to move my applications and data back onto my machine. My final step was to completely erase my time machine backup, encrypt that time machine drive and then do my encrypted time machine backup. Too many steps and not at all efficient.


Good luck again.

Feb 8, 2014 7:11 PM in response to Mark2006

brief update -


the command


hdiutil chpass yourmachine.sparsebundle


will allow you to change the password that generates the encryption key(s) for the time machine backup stored inside of the sparse bundle image, but does not allow you to remove the encryption completely. Setting a blank password simply sets the password empty, but OS X will still prompt you for a password when trying to mount the sparse bundle. In that case, just hitting return for a blank password works fine if you changed it to be blank as I did. I did not go through the trouble of seeing if DMA did anything different since it was clear the TM backup was still encrypted.


To remove the encryption, you have clone the image essentially, with the clone never having encyption turned on. It seems one can always turn on encryption to a sparse bundle, but once its on, never get rid of it. Here is what I did to create an unencrypted sparse bundle that is for all intents and purposes, to the best of my knowledge, an exact duplicate of the original except in the file name (well, directory name I guess) of the sparse bundle itself:


hdiutil convert basmati.sparsebundle -format UDSB -o basmati-noenc.sparsebundle


where basmati.sparsebundle is the TM backup that I copied off my time capsule onto the local disk of the loaned computer.


Creating that copy first is not necessary - I did that first because I was afraid to try hdiutil chpass on the encyrpted bundle in case it rendered it inaccessible. A blank password is kind of a corner-case that might expose a bug not seen in testing or that often in the wild. One can create the needed unencrypted copy directly from the time capsule with the hdiutil convert command above, and the -o option can send it either back to the time capsule (that will cause I/O contention at the TC and slow things down considerably, not recommended) or to an attached external disk, or the internal disk. I successfully did it to the local disk, and then was able to mount the sparse bundle and it did not ask for a password.


DO NOT attempt to create a sparse bundle with "hdiutil create", mount the encrypted sparse bundle, and then copy the contents of the mounted encrypted sparse bundle into the new one. This will not work. I'm not sure what the problem is with that. I tried it first. It gives all kinds of errors. It may have to do with File Vault being on as well on my original system the TM backups were made from and the contents of the sparse bundle not being readable because of a double encryption. My other thought was that the user and group ids do not match between my original system, and this loaner system. None of it seemed to be a problem using "hdiutil convert".


Status: I'm pushing the unencrypted clone of the TM backup to a thunderbolt external drive now. Copying back to the TC takes too long - its one of the older, original models. I'll try DMA from that once its there. I don't know if there is something else needed for DMA to recognize the sparse bundle as a TM backup but at least now DMA can snoop inside it when it is "scanning" for TM backups.

Feb 9, 2014 2:38 PM in response to slowkoni

Update: Data migration assistant won't recognize the sparsebundle on the external drive as a TM backup it can use. I then pushed it overnight back to the time capsule and put it in place of the original encrypted backup. It still did not work.


What did work: Reinstalling OS X 10.9 on the loaner system from scratch via command-R, then using Setup Assistant to pull my files but not the OS from my time machine backup. Setup assistant runs the very first time the system is booted after clean install and apparently is a different beast all together than Data Migration Assistant despite them being very similar in interface and function. Setup Assistant was able to recognize the copy of the encrypted sparsebundle TM backup that was now on my new external thunderbolt disk, the one that I had changed the password to a blank password. It did not recognize the clone I created as described above with "hdiutil convert". It prompted for a password and I just hit the return key, and it started restoring all my apps and files. The key here then is to do this on the very first boot after clean install when Setup Assistant is invoked and before a normal user account is created on the new install of OS X. That seems to be the only opportunity. DMA just doesn't work.


Irony: Once the restoring process was well underway and about to finish, the Apple store called and said my system was repaired and ready for pickup today (a Sunday even), several days earlier than expected. Shrug.

May 3, 2014 4:49 AM in response to slowkoni

This is a message to slowkoni


I have got the problem you describe. I called AppleCare about an issue and I ended up wiping my mac with the plan to use migration assistant to recover my encrypted TM backup.


However. I was using FV2 and now the process gets stuck asking for a password for the mymac.sparsebundle. I've tried everything!


So I am going to try your hdiutil convert. However, I've never used command line.


Would it be possible to write a simple step by step process?


I've copied the sparsebundle to my mac and ready. I then plan to put on external storage. Wipe the mac and then restore from the external hard drive


Your help would be so appreciated. I can't find anything on the net related to this. AppleCare say it's tough. And stupidly it's the only backup I have. Any help would be greatly appreciated.


Many thanks

May 3, 2014 7:32 AM in response to Wisdom Heart

Hi Wisdom Heart,


If you have forgotten the password, the "hdiutil convert" command won't be of use. I'm not sure if "tried everything" refers to the password (we've all been there!), or to trying to get the system to use your TM backup to restore files. The first thing you need to do is establish access to the files in the TM sparse bundle, then the trouble is to access them from the right tool. What I describe above is that Data Migration Assistant can not seem to use an encrypted time machine backup, does not even recognize them. However, "Setup Assistant" can. This program however is only run once, the very first time you boot after a clean install. There may be a way to invoke it manually but I don't know how. What you should do is this:


1. Mount the volume with the TM backup

2. Open disk utility, select the TM sparse bundle, and select "unlock volume" (or something like that)

3. Enter the password. If you have to try several, make sure to note the one that works. Important: the TM backup encryption password is not the same as the FileVault password or key. It would have been entered separately.

4. Close everything and reboot with command-R

5. Reinstall OS X Mavericks

6. On first reboot after reinstall, technically still part of the install process I guess, pay close attention for Setup Assistant. It will probably ask you if you want to migrate data from an old machine or backup or something. I don't remember exactly, but you want to take this opportunity to do so, not later via Data Migration Assistant

7. In Setup Assistant, connect your external drive or scan the network for your time capsule or network share that has the TM backup

8. This time, SA should show you the TM backup to select where as DMA acted like nothing was there (in my case). Select your TM backup, it will ask for the password. Enter the password, and everything should flow easily after that.


Hope that helps. Good luck!

Clean Install Problems With Encrypted Time Machine

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