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BootCamp Windows won't boot after turning on disk encryption

Hello everyone, I'm in a desperate situation and I need your help. Here's my sitatuaion.


I have 13-inch MacBook Pro (Early 2011). I put an SSD in it as my main drive and I also put an additional drive (HDD) in the optibay in place of my superdrive. The structure I had was this:


1) My entire SSD was my OS X disk.

2) My optibay HDD had three partitions: a) Time Machine backup partition, b) Extra partition (for stuff like media), c) Windows partition with Windows 7 installed.


Had that setup for a long time and everything was working fine, my SSD was being backed up to the Time Machine partition on the HDD in my optibay.


Then, I decided to turn the File Vault 2 on. First I did it for the SSD with my OS X on it. Everything went well and I could still boot into my Windows 7. Then, I decided to encrypt my Time Machine backup (because what's the point of encrypting the main system disk if you don't encrypt the backup as well?) - here too everything went fine.


That is, until I needed to boot into Windows. I restarted my Mac, held down the Option key, the chooser thingy came up but there was no Windows to choose from. I happened to me once before (but in a different scenario, no disk encryption involved), so I knew I may still be able to boot into it.


I popped in my USB thumbdrive with rEFIt on it, selected it and it gave my the option to boot into the Windows partition. Only this time this did not work, I got an error message telling my there's no bootable device or something like that.


I'm confident turning the disk encryption for the Time Machine partition (which is on the same HDD as my Windows partition) screwed things up here.


The only question is: can I still fix it, boot into Windows, without having to install it from scratch? What I want is to have the disk encryption turned on for both my main SSD where I have my OS X installed AND the Time Machine partition which is on the HDD in the optibay and also have a Windows partition on it, but still be able to boot into Windows.


I'm running 10.11.13 El Capitan.


Can you help me in any way? Here's my diskutil cs list:


/dev/disk0 (internal, physical):

#: TYPE NAME SIZE IDENTIFIER

0: GUID_partition_scheme *128.0 GB disk0

1: EFI EFI 209.7 MB disk0s1

2: Apple_CoreStorage Macintosh SSD 127.2 GB disk0s2

3: Apple_Boot Recovery HD 650.0 MB disk0s3

/dev/disk1 (internal, physical):

#: TYPE NAME SIZE IDENTIFIER

0: GUID_partition_scheme *500.1 GB disk1

1: EFI EFI 209.7 MB disk1s1

2: Apple_CoreStorage Time Machine 150.0 GB disk1s2

3: Apple_Boot Boot OS X 134.2 MB disk1s3

4: Apple_HFS Extra 300.0 GB disk1s4

5: Microsoft Basic Data Windows 49.5 GB disk1s5

/dev/disk2 (internal, virtual):

#: TYPE NAME SIZE IDENTIFIER

0: Apple_HFS Macintosh SSD +126.8 GB disk2

Logical Volume on disk0s2

406F3A62-89AE-4F91-BEEF-B8CE0B16C8EF

Unlocked Encrypted

/dev/disk4 (internal, virtual):

#: TYPE NAME SIZE IDENTIFIER

0: Apple_HFS Time Machine +149.6 GB disk4

Logical Volume on disk1s2

0567D276-3738-4776-9CC5-B69F922B0A0C

Unlocked Encrypted

MacBook Pro (13-inch Early 2011), OS X El Capitan (10.11.3)

Posted on Feb 12, 2016 11:10 AM

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Posted on Feb 13, 2016 6:27 AM

Your problem is unrelated to FileVault2. Your issue should have started when Apple_HFS Extra was created. Please post the output of


sudo fdisk /dev/disk1


If you have an issue with your Mac, you can potentially lose both the SSD and TM Backup. It is not an optimal setup. A TM should be physically separate from your Mac, so you can restore the TM Backup to a new Mac, if necessary.


Also, since you have removed the Optical drive, re-installing Windows on your 2011 model is a very rough road to travel.

30 replies
Question marked as Best reply

Feb 13, 2016 6:27 AM in response to Roziek

Your problem is unrelated to FileVault2. Your issue should have started when Apple_HFS Extra was created. Please post the output of


sudo fdisk /dev/disk1


If you have an issue with your Mac, you can potentially lose both the SSD and TM Backup. It is not an optimal setup. A TM should be physically separate from your Mac, so you can restore the TM Backup to a new Mac, if necessary.


Also, since you have removed the Optical drive, re-installing Windows on your 2011 model is a very rough road to travel.

Feb 12, 2016 7:24 PM in response to Loner T

Was hoping to get a response from you 🙂. Fortunately, I managed to resolve the issue using GPT fdisk and your answers to folk with similar problems here on the forums.


There was no problem when Apple_HFS Extra was created because I worked around it. The setup I have right now is it optimal for my needs, but to achieve that I had to dance around.


1) put the HDD in the "main drive slot" (take out the SSD temporarily)

2) put the superdrive back in

3) partition the HDD so it has three partitions:

- Time Machine

- Extra

- Windows

4) Install Snow Leopard on the Time Machine partition (for whatever reason, everything Lion and up would not work when trying to achieve the setup, it wouldn't boot into Windows)

5) once booted into Snow Leopard, using Disk Utility, make the Windows partitions a FAT32

6) put in Windows DVD installer into superdrive

7) Install Windows on the Windows partition

8) take out HDD

9) take out superdrive

10) put the HDD into an optibay and put the optibay in the place of superdrive

11) put my SSD in the "main drive slot"

12) install El Capitan on the SSD

13) erase the Time Machine partition and set it up with Time Machine


- I needed to have a bootable Windows on my Mac, but didn't want to waste my SSD's space

- I wanted it to be the last partition on the drive, so when I don't need it anymore, I could easily delete it and merge the space with the Extra partition that's right before it


Also, I do have other backups (one more external Time Machine, external SuperDuper, and cloud-based Backblaze), but what I wanted to have was a local Time Machine backup in case of the SSD dying.


I should have anticipated that turning on encryption would mess things up, turning it into a CoreStorage volume or something.


Anyhow, thanks for your help, as it is your replies on the forums to similar topics that helped me resolve it 🙂.


P.S. Yeah, if something breaks and I need to install Windows again, that's gonna be a real pain, as it won't let me install it via USB thumbdrive (even when "hacking" BootCamp assistant) + Windows won't install from an external USB-connected optical drive. I'll have to put the superdrive back in and play this horrible game again... But hey, that's the price for having such setup.

Feb 12, 2016 8:24 PM in response to Roziek

Please setup a daily regimen of backups of everything. You should consider a second external TM destination. It is allowed. You can exclude the internal TM part. For Windows, I will also suggest a Windows System Restore point before any Windows Updates are applied. I have Windows Automatic Updates disabled, but I check every week and discard any driver updates.


You did eventually travel the 'rough road'. Glad to see you got there.

Feb 13, 2016 6:27 AM in response to Loner T

That's exactly what I have now, sir 🙂 :


Also, I do have other backups (one more external Time Machine, external SuperDuper, and cloud-based Backblaze), but what I wanted to have was a local Time Machine backup in case of the SSD dying.


I just don't want to pass on the internal Time Machine backups, as it's very convenient, the drive is always connected - unlike anything that's external - and I have a versioning for my files/system just click away. I plug the external with a SuperDuper once a day, at the end of the day, and my external Time Machine is is plugged in when I'm sitting at my desk (which is about half the time I'm working).


Anyway, I'm giving you "points" (or whatever it is, I'm new to the system and community), as it is your answers that helped through the problem (just not from *this* topic), I hope that's ok 🙂.

Feb 13, 2016 8:02 AM in response to Loner T

Actually, maybe you could save me future problems right now 🙂.

Is it possible to achieve the setup I described in previous posts, but without going back as far as Snow Leopard, without installing *any* OS X on the HDD at all?

Please, read carefully my previous post regarding the way I did it before you answer, as it's crucial:

1) put the HDD in the "main drive slot" (take out the SSD temporarily)

2) put the superdrive back in

3) partition the HDD so it has three partitions:

- Time Machine

- Extra

- Windows

4) Install Snow Leopard on the Time Machine partition (for whatever reason, everything Lion and up would not work when trying to achieve the setup, it wouldn't boot into Windows)

5) once booted into Snow Leopard, using Disk Utility, make the Windows partitions a FAT32

6) put in Windows DVD installer into superdrive

7) Install Windows on the Windows partition

8) take out HDD

9) take out superdrive

10) put the HDD into an optibay and put the optibay in the place of superdrive

11) put my SSD in the "main drive slot"

12) install El Capitan on the SSD

13) erase the Time Machine partition and set it up with Time Machine


I have another MacBook Pro that I'd like to setup up the same way, but it would be great if I could do that like this:


1) have my SSD as it is, with El Capitan on it

2) connect that HDD externally (via USB) and partition it using DIsk Utility as follows:

- Time Machine (partition 1)

- Extra (partition 2)

- Windows (partition 3)

3) put superdrive back in

4) put that HDD in the "main drive slot", instead of my SSD

5) pop in a Windows DVD installer and proceed to install Windows on the Windows partition of the HDD

6) at the end, take out superdrive, put that HDD in there in optibay and put my SSD back in the "main drive slot"


And of course, have that Windows be perfectly bootable. Is that possible?


That would spare me the one step and a chunk of time, as I wouldn't have to install Snow Leopard on the Time Machine partition and use it to create the Windows partition (and that hybrid MBR thing).


I tried that before, and it all works fine up to certain point: I can install Windows, but it's not bootable afterwards, I can't select it during the boot and - if memory serves - even rEFIt was not able to boot it.


So, my guess is, Snow Leopard creates some hybrid MBR on that HDD, when I partition in from within the OS (as in, create a FAT32 Windows partition), and that hybrid MBR is not created when I do that "externally" (just connecting the drive via USB) - then it's just partitioning, but the option to boot into that Windows is lost/hybrid MBR is not created.


Is it possible to do what I described without falling back to Snow Leopard and relying on it to create a hybrid MBR or something?


Could I do that using that GPT fdisk tool?


P.S. Sorry if my instructions are not clear, english is not my native language.


P.P.S. What is strange is that it only works on Snow Leopard. If I try to install Lion or any later version and partition the HDD, it doesn't create that hybrid MBR and after installing Windows - it's not bootable. Any ideas why?

Feb 14, 2016 6:50 AM in response to Loner T

Yes, they basically have the same setup.


Both have a 128 GB SSD as their main drive.

Both have their superdrive replaced with an optibay sporting a bigger HDD.

Both are running the latest stable 10.11.3 El Capitan 🙂.


And both have the same partition setup.


SSD is a one big partition with the OS on it.

HDD is sliced into three partitions:

1) Time Machine

2) Extra

3) Windows


Would be awesome if I could skip installing any on on the Time Machine partition and go straight into installing Windows and somehow making that whole hybrid MBR shebang work, so I can boot into Windows no problems.

Feb 14, 2016 7:30 AM in response to Loner T

Not only did I consider it, I tried it 🙂. Not gonna go into details, but it's not gonna work for what I need here.


Anyway, I have the optimal setup for me right now, the only question is - is it possible to achieve it without having to install OS X on the Time Machine partition and using it to create the hybrid MBR. So basically, I have my ideal setup and I have a way of achieving it, but I'm looking for an easier and faster method.

Feb 14, 2016 8:14 AM in response to Loner T

Actually, that's not the problem 🙂. I'm willing to put in the superdrive to install Windows (tried it many times, it won't install from an external optical drive - and like you said, my particular Macs won't install from the USB thumbdrive either, made my peace with that long time ago). What I want is to be able to entirely skip the part with installing OS X on on of the HDD's partitions to make the hybrid MBR and have the Windows be bootable after the installation.


I've tried this many times:

1) partition the HDD from Disk Utilisty (running on my SSD's OS X); like I said many times, three partitions: Time Machine, Extra, Windows

2) put in the HDD and put in the superdrive

3) install Windows


It installs fine, but there's no hybrid MBR in that scenario, Disk Utility does not create it, so even though I was able to install Windows, I'm not able to boot into it afterwards (even using rEFIt).


That's why I revert back to the old way of doing that: installing OS X (older version) on one of the HDD's partition (that one that later will be a Time Machine partition), partition it, make the Windows partitions FAT32. That creates the hybrid MBR, so after installation I'm still able to boot into Windows, and I can go back to my setup: putting the HDD with in the optibay and my SSD in the main slot.


Also, I noticed there's always a problem when there's three or more partitions (same with Fusion Drive). BootCamp works fine with two partitions, meaning, one is the OS X, the other is Windows. But that's not suitable for me.


Like I said, I do have my ideal setup right now; I'm looking for a way of recreating it with less steps and less time spent.


My ideal scenario would be this:

1) partition the HDD when it's plugged in as an external drive, be it via USB

2) put it in

3) put the superdrive in

4) Install Windows from the optical drive

5) somehow, after that, create that hybrid MBR so I can actually boot into Windows after installation


This would save me a painful step, and a time consuming one (installing a temporary OS X).


Would be awesome if GPT fdisk could do just that.

Feb 14, 2016 10:14 AM in response to Roziek

Roziek wrote:



My ideal scenario would be this:

1) partition the HDD when it's plugged in as an external drive, be it via USB

2) put it in

3) put the superdrive in

4) Install Windows from the optical drive

5) somehow, after that, create that hybrid MBR so I can actually boot into Windows after installation


This would save me a painful step, and a time consuming one (installing a temporary OS X).


Would be awesome if GPT fdisk could do just that.

Step 3a - Create Hybrid MBR using GPT Fdisk. This should address your issue. The GPT Fdisk 'r' and 'h' commands can be used. They are used most often when I have to rebuild MBR installation. Please see the Rebuild MBR part in Re: El Capitan has deleted my bootcamp windows partition as an example of rebuilding the MBR once the GPT is already in place.

BootCamp Windows won't boot after turning on disk encryption

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