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I think that this is not possible anymore.

The repair option to boot to the cd is no longer an option due to the changes in setup for Windows Server 2008. Since it uses a image based deployment option, the file by file copy method is no longer available.

You can boot to the Windows Server 2008 and choose the repair in the lower left hand corner of the screen. this should open a CMD prompt.

From here you can run sfc and use the offline options,

/OFFBOOTDIR For offline repair specify the location of the offline boot directory

/OFFWINDIR For offline repair specify the location of the offline windows directory

This repairs the boot files, allowing you to boot back into the OS, if you are still having issues you could try doing an upgrade with the media then.

http://social.technet.microsoft.com/Forums/en-US/winserversetup/thread/cd3d665f-3d95-4617-946d-55d8c03448fe

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