It sounds like this is a bug in Windows and not in Ubuntu, as long as
Windows keeps modifying the MBR.

Another possible workaround would be to use the Windows boot loader, and
modify boot.ini to reference either grub for Windows (grub.exe/GRLDR) or
a file containing a copy of the boot sector where grub was installed.

http://ubuntuforums.org/showthread.php?t=56723 (XP)
http://forums.fedoraforum.org/showthread.php?p=789492 (Vista)

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after boot into Windows XP, grub menu is not displayed and computer reboot
https://bugs.launchpad.net/bugs/26058
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