Consider a Virtual SBS 2003 to SBS 2008 Migration

Consider a Virtual SBS 2003 to SBS 2008 Migration

If you carefully follow the recommended preliminary health check and update steps, the likelihood of a smooth migration is significantly improved. Nonetheless, any migration involves a degree of risk as Windows SBS migration makes permanent changes to your Windows SBS Source server – for example, moving e-mail accounts. Therefore, all migrations should begin with a backup of the pre-migration Source server. This backup should be sufficiently complete and fully tested.

 This article discusses using virtualization as a simple and low-risk backup method for migrating Windows SBS. A virtualized migration can be done in four stages.

  Stage 1: Virtualize Windows SBS


  1. Arrange your servers. There are three servers for this process: the Source server (SBS2003 physical), the Destination server (SBS2008 physical), and a host virtual server (SBS2003 virtual). The host virtual server should have sufficient memory and disk space to handle the SBS2003 virtual machine. If resources are tight, consider using Virtual PC 2007 for virtual machine management (
  2. Create a virtual image of the SBS2003 server. On the SBS2003 server, run a tool like Disk2vhd ( to create a physical-to- virtual image (P2V) of your SBS2003 Source server.
  3. Back up the virtual image. There are a couple reasons to do this.  First, if for some reason you want to restart your migration, this image is ready to go. Second, in Stage 3, you repurpose your existing physical SBS2003 server and reformat the drive. Should you need to go back to a pre-migration instance of your SBS2003 server, this backup provides the image to do that.
  4. Copy the SBS2003 virtual image to your virtual host server.
  5. Disconnect the SBS2003 physical server from your network.
  6. Connect the virtualized SBS2003 server to your network and check to see if it’s reachable from clients.
At this point, the virtualized SBS2003 server is now the Source server and migration will be run against this virtual server. The SBS2003 physical server remains untouched and ready to resume normal operations should you need to back out of the migration. Restoration is as simple as swapping network connections. The physical SBS2003 server is your complete and tested backup.

Stage 2: Migrate SBS2003 to SBS2008

In Stage 2, you go through the normal migration process migrating the virtualized SBS and leaving the physical SBS untouched.

 Stage 3: Install LOB applications


 In Stage 3, after reaching the point where your SBS2003 is nearly complete, you can repurpose your physical SBS2003 server for line of business (LOB) applications or for other purposes. Repurposing the physical SBS2003 server involves reformatting the system partition on the physical server. Because you created a backup of the pre-migrated SBS2003 in Stage 1, you will be able to load this image as a virtual machine any time you need to access the pre-migration SBS2003 server.

 Stage 4: Complete the Migration


 In Stage 4, you complete the migration. SBS2008 is running on a new server, LOB applications are running on the old server, and the virtual host server is freed up and ready for a new assignment.



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  • i'm currently looking at doing this, the only concern i have is how exchange is handled as the production machine will still be running while the transition is happening, so the 2008 server may be a week out of date. what is the best process to bring exchange into line

  • That's a good question. I was thinking of exporting mailboxes from Exchange 2007 as PST and importing into Exchange 2003 using ExMerge but I'm no expert on this process. I'll post on a newsgroup and see what the experts say and follow up here.

  • exmerge was how i was thinking of doing it, didn't think i could forklift the exchange 2k3 database and throw it at 2k7.

  • one other issue that has popped up with this is that of activation if your using oem installs

  • I had the same situation a week ago (upgrade from SBS2003 to SBS2008 on same hardware), the only difference was that i was using Citrix XenConvert & Xen Server. However, when i booted virtualized SBS2003 i could not log in due to the fact that XenConvert cannot virtualize open files, services and so on... It then corrupted AD and had to do it "old fashioned way", from existing SBS2003 to temporary SBS2003 on another server and then from temporary server back to SBS2008 on primary server.

    My question is, can disk2vhd tool succesfully convert AD and other running services, so that they boot with no problems in virtualized environment. If so, i wish i had this info one week ago. It would save me 20 hours of mailbox moving :(



  • i used vmware p2v and it worked a treat, currently in the process of doing the migration this week, no issues with AD at all (so far). Have had general issues however based on source server. Mainly annoying more than showstopper stuff.. however i wouldn't be too happy to do this process in a live production environment. Fair chance of making a rod to beat your own back with. The server goes into customer site this saturday.

  • Great concept.   We have used a virtualized Exchange environment since moving our Exchange 5.5 to a VM, then taking that VM, a copy of AD and a new VM for Windows 2003 / Exchange 2003 Enterprise Edition on a dedicated workstation running VMware Workstaiton, and we went through the migration until we got it right.  The production migration, after the full backup was superb.  

    Regarding migrations (P2V) -- please go the cold migration path.  If you are using vmware p2v (now called Vmware Enterprise Converter unless you have the earlier Standalone Converter licenses), you download two images and you can make a bootable ISO that your physical server can boot from during a maintenance window on your Exchange server.  Once you tell the converter where to place the converted 'virtual disks', you will be able to walk away (Yes, I monitored it for a few trials, but it was four hours for us over a 100MB WAN connection to new corp HQ).    Previous attempts to use P2V as a hot backup or to use the Windows NTBACKUP mechanisms doesn't give you the same 100% solid result the P2V off the bootable ISO does.

    We will be migration SBS 2003 to SBS 2008 and the first software on the new server will be VMware.   The only corporate email server (after we decommission SBS 2003) will be Windows SBS 2008 and additional Server 2008 Standard licenses.   Microsoft Applications on Virtual Windows Operating Systems on VMware is great for small offices with Open Licenses and large enterprises with EA agreements.

  • Given the rise of people running servers virtually, I'm surprised the article doesn't mention the possibilities of the final destination being a *virtual* SBS 2008 server (the intention in our company).

    Does anyone know the implications of this?  We were hoping to have one Hyper-V server with the SBS 2003 and SBS 2008 servers running on it.  Presumably the 'migration' method mentioned is a swing migration?

  • HI All,

    you have to be careful because SBS 2003 is not supported on virtual environments as you can verify with the virtualization support wizard:

    This means that any issue that may arise will not be supported by CTS unless support policy aren't changed.

  • ...well "until" policies aren't changed

  • I tried this before reading the article. I'm still in process, however. I used Acronis Backup and Recover with Universal Restore to make an image of the system drive. Then you can convert to Virtual PC image fromt he application itself. The thing that's different for me is I took the image out of the office and did all but last few steps of migration in a different location. I'm going to be taking the new 2008 server back without finishing Folder Redirection policy implementation, Exchange 2003 uninstall, and 2003 DC demotion. I completely spaced that those last 2 steps have to be done with clients connected :/ I hope the live physical  2003 SBS can see and sync with AD in the 2008 SBS once I hook them up. I had virtual server for 2003 configured with the same IP, as the physical machine. Keeping fingers crossed. Once done, I will use ExMerge to take out the latest messages (from the time between image creation and today) and import them through PowerShell into 2008. However, I will need to find a 32-bit client with Outlook on it to run the script *facepalm* Thanks, Microsoft.

  • Made VHD from live SBS2003, and created virtual SBS2003 on another PC using Virtual PC.  It works fine until login, when attempted to login to the virutal SBS2003, it tries to validate the OS and it fails, kicking me out back to login screen.  I'm assuming this is due to the hardware change?  Is there a way to fix this?


  • Carsten Siemens edited Revision 5. Comment: Added tags: en-US, has comment, has image

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