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I have a computer running Windows XP Pro 32-bit and 64-bit in dual boot.

I need to retain Windows XP 32-bit Pro, as I have expensive software that will only run on that specific version. I want to upgrade my 64-bit installation of XP to Windows 8 without losing the 32-bit installation.

If I simply use the ISO to upgrade from within my XP 64-bit installation, will I retain dual boot for both XP 32-bit and Windows 8?

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Yes, that should work. Because you are dual booting and the PC see's two MBR's, upgrading the second boot will retain it. Hopefully the 32 bit was the first installed and the 64 was the second, because the first install has the dual booting MBR.

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Unfortunately, no. I mistakenly assumed the 64-bit version of XP would be superior, and later found that some software simply would not run on it. I bought and installed XP pro (32-bit) later and installed it. – Shane Nov 24 '12 at 12:01
If you don't reformat the partition with 64 bit of XP, the bootloader for 32 bit XP will most like stay on its place, and Windows 8 setup will automatically configure your system for dual boot between Windows 8 and Windows XP (32 bit). If you reformat the partition, you would need to restore booting to Windows XP using the built-in command bcdedit or using 3rd party tools like Easy BCD Edit. – Alexey Ivanov Nov 26 '12 at 19:59

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