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    Windows 7 to 10 upgrade with TrueCrypt? ☶ ask windows
    tedu avatar authored by tedu 3 years ago | 2 comments

I have a laptop running Windows 7, using TrueCrypt full disk encryption. Since it’s now Windows 10 upgrade season, I get regular popups asking me to do so. I’m a bit wary that the upgrade is likely to break halfway through leaving me with an unbootable system.

Searching the web leads to posts from others with the same question, such as http://superuser.com/questions/949519/windows-10-upgrade-and-truecrypt. Always with the same unhelpful answer. “TrueCrypt is no longer supported.” Yes, yes, I already knew that.

Since I do not have so many machines or so much time as to experiment myself, I’m turning to Lobsters as a last resort. I imagine encrypted Win7 systems can’t be that rare among the crowd here. Has anybody attempted such an upgrade?

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    calvin avatar calvin 3 years ago | link

    It seems very unlikely, considering it hooks at the bootloader level. By looking around:

    I have whole drive encryption using TruCrypt. I started the upgrade process and all looked like it was working. However, when the computer reboots and I put in the password, the upgrade lets me choose my install language, but then reports that part of the drive is locked and it drops back to Windows 7.

    (Also there: “You need to contact TrueCrypt support about support.” Ohhhhhh, Microsoft support forums, how useless you are.)

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      tedu avatar tedu 3 years ago | link

      Thanks. You’d think “Been there, done that, didn’t work” would outrank any answers offering vague suggestions…