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Is there software that can help automate (or make it repeatable) setting up PC's or lab servers where the setup includes GRUB for bootloading multi-boot for Windows, Debian, CentOS, etc.

I was originally looking at tools like Boxgrinder and Cobbler, but with GRUB in the picture I'm not sure if those are appropriate.

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Yes... and No....

Kickstart as part of it's installation process will configure Grub automagically. In addition you can manipulate the grub configuration files during the post install process. However it sounds like you are looking to set up a system which may involve multiple OS's which can be more of a challenge. There are may tools out there which can allow for the pushing of system (disk) images in a manner similar to cloning, but these methods have their limitations. The limitations often center around system specific configuration such as ssh host keys and module detection/configuration files. I don't use Windows so I don't know what specific ones relate, but I know there are similar issues.

One option may be to build a LiveCD for installing everything onto the system in question. The process would work in a similar manner to the Fedora Live Image installers. You put in a Disk for Flash key, boot and a kickstart script is run. This script can handle partitioning the disks, fixing grub etc. In addition you could deploy a Windows disk image to one of the partitions created during your automagic partitioning during kickstart. You will want to run the sysprep program on the Windows system before creating the clone image, this way all system specific information is scrubbed making the clone process work.

Overall this process may not be simple in your initial runs, but you may find it to provide you the most flexibility in the long run.

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