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?
Answer
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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