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I know that GRUB (and GRUB2) can chainload a Windows OS if you specify the hdd that it is contained on. Is it possible to tell GRUB (or GRUB2) to boot into a dd image-file of a Windows OS that is located on a Linux filesystem? Alternatively, is it possible to use some other bootloader to accomplish this?

I'm not trying to run a VM, but rather run the system as if it were the main installed OS, with little overhead. I've seen something sort of like this done from Android to Linux using chroot, but Windows itself doesn't support chroot or boot in the same way as a Linux system.

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I have, since asking this question, found this to be impossible - Grub's filesystem access goes away when it starts the OS, so the system can't do anything. Even if you set it up and tell grub to do it, it just hangs after you select the entry. –  Suchipi Mar 3 at 10:13

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