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A client of mine has a computer running applications for roughly 10 machines. They need a real server to handle all of this and I'm going to make some recommendations and install/migrate everything.

Because they are running legacy apps I'm going to create a virtual hard disk of the old operating system and run it on the new server within virtualbox.

I want to make sure this process goes as smoothly as possible.

What information do I need to gather from the old computer and the new server to ensure maximum compatibility in this migration?

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What OS does the legacy host run? If Windows, I'd do an ASR backup and then restore it to the virtual machine, which should produce a running system. (The info there is described as Server 2003-specific, but the process is broadly similar across all Windows versions supporting ASR.) –  Aaron Miller May 6 '13 at 21:12
    
For Linux it should be even simpler -- from memory, you'd bring the legacy box up in single-user mode, dd a backup of its disk(s) to an external device, boot a live CD on a VM with suitably sized virtual disks, pour the backup onto the virtual disks via dd again, install GRUB, and reboot the VM without the live CD to bring up the legacy system. –  Aaron Miller May 6 '13 at 21:14
    
I haven't been onsite yet, but I want to say the old "server" is running XP or some desktop OS. Over the phone she sounded wizened enough to know that what they had was a PC and what they needed was a server. –  Scandalist May 6 '13 at 21:26
    
XP supports the ASR backup method; you'll need an XP install disc and a floppy drive to complete one, as part of the ASR process includes writing a disk that you'll be prompted to provide during the XP install process -- this means you'll need both to be able to image that floppy and mount the image on the virtual machine during XP install, and to do the same with the actual backup created during the ASR process; since the data on the disk is used to point the XP installer at the backup, you'll need the latter to appear to the VM as a mounted hard disk, which likely shouldn't be too difficult. –  Aaron Miller May 6 '13 at 21:35

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