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Windows 10 update

Topics: Users Discussion
Jul 29, 2015 at 5:57 PM
Now that starting today (29/7) we can upgrade to Windows 10 from 7 and 8 from inside the OS,
is it safe, or even, doable at all to upgrade a fully encrypted disk ?

(I mean the system drive which is fully encrypted, no non-system partitions or containers).

Or I will brick it / kill it ?
Anyone tried ?
Jul 29, 2015 at 6:03 PM
Edited Jul 29, 2015 at 6:12 PM
Per the VeraCrypt FAQ documentation, you must decrypt system encryption before performing OS upgrades.

PS: I would disconnect any encrypted external drives to prevent Windows upgrade utility from being too helpful by auto initializing the encrypted disks since Windows sees the drives as raw format. Have backups of your data for internal non-system encrypted disks or partitions. Just a warning I have seen on the TrueCrypt forums in the past.
Aug 5, 2015 at 4:32 PM
What would be the most efficient way to do this for an install of Windows 10 on an system encrypted SSD drive? I would assume decrypting the drive would open up the same issues that apply to encrypting SSDs with data already on them?
Aug 5, 2015 at 4:55 PM
One idea would be to create a file container and move all your sensitive data into the file container. Then decrypt the OS, upgrade to Win10, encrypt OS and then mount the file container to copy the sensitive data back to the original locations.

This is not fool proof if you are worried about entries in the Windows registry or other data leaks due to some applications use their own "database" to remember recently used files and locations or possibly create their own temp files.

The only secure method would be use the file container on an external HDD to copy your sensitive data and perform a fresh install of Win10 on the still encrypted OS drive. You will need to format the SSD and recreate the MBR to destroy the VeraCrypt bootloader before installing Win10. You can Google search using TrueCrypt to get the procedures.

Does anyone else have a more secure approach to upgrade the OS using a VeraCrypt encrypted OS SSD drive?
Aug 6, 2015 at 10:05 AM
Edited Aug 6, 2015 at 10:06 AM
I have actually tried to upgrade windows 7 to windows 10 whilst the whole system drive was Encrypted, and no there is no issue apart from the fact you just cannot upgrade windows whilst it is Encrypted, it will just fail to download when Windows reboots your system to begin the installation.

What happens is that the system will ask to restart to install windows 10, once you begin the restart windows will configure settings for installation and then it will restart, to which you will then need to sign into your encrypted drive to which it will move onto a screen that looks like windows 10 which will ask you for your keyboard and language settings and then it will come up with a trouble shoot page with two options - troubleshoot or shutdown - all you need to choose is shutdown and you'll be back to normal; you'll logg on as normal and windows will notify you that the install for windows 10 failed; all you have to do is decrypt your system drive and begin the installation again (and it will be perfectly fine, as I am typing this from that very computer now running windows 10)

Hope that helps.

tldr; It does not cause any issues; it just fails to download. Your computer will run like normal like you never installed windows 10, all you need to do is decrypt your drive and begin the upgrade once again to get windows 10