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I am running Windows 8.1 Pro and my system drive is encrypted with DiskCryptor. This means that I need to enter my key before Windows will boot.

After having read that some people managed to upgrade from Windows 8.1 to Windows 10 with Bitlocker enabled, I am curious:

Can I upgrade Windows 8.1 to Windows 10 without decrypting my DiskCryptor-encrypted system drive?

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  • Note that according to their website (diskcryptor.net/wiki/Main_Page), Windows 10 is not yet supported.
    – ChrisInEdmonton
    Commented Aug 6, 2015 at 16:46
  • @ChrisInEdmonton Yes, I saw that but I am not sure whether this is due to lack of support or due to the page being outdated.
    – Chris
    Commented Aug 6, 2015 at 16:47
  • You being able to do this Bitlocker is entirely different then having a third-party encryption enabled. If you want guaranteed success, decrypt the disk, then perform the upgrade and encrypt it again. we can only point to the fact the official documentation says Window 10 is not supported. Any specifics questions about if the documentation is accurate should be ask on their forums.
    – Ramhound
    Commented Aug 6, 2015 at 16:49
  • @Ramhound I realize that this is the safer way but I was hoping that someone could share their experience whether it works without decrypting the entire disk.
    – Chris
    Commented Aug 6, 2015 at 16:50
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    For what it's worth, when I asked Microsoft about BitLocker, they told me that the Windows 10 setup suspends and resumes it for the upgrade.
    – David Marshall
    Commented Aug 6, 2015 at 17:03

2 Answers 2

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I (accidentally) upgraded the machine to Windows 10 without disabling DiskCryptor. On shutdown a message similar to the Windows Update message appeared (on the uniform colored screen), telling me that the upgrade to Windows 10 is being prepared.

After reboot the unlocking of the disk with DiskCryptor still works but Windows only boots into a recovery menu that allows me to turn off the PC or execute some recovery options. None of those work, most of them terminate with an error message right away.

So to answer the original question: No, you can not upgrade from Windows 8.1 to Windows 10 with a DiskCryptor-encrypted system partition.

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To be absolutely safe. decrypt before trying to install windows 10. I had to uninstall diskcryptor and header before 10 would load. With diskcryptor the restart was the problem, after entering password on restart windows directed me back to 8.1. After decrypt and uninstalling diskcryptor/heading and signing into MS account, had no more problems.

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