The swing style route to Small Business Server 2008 from Server 2000 without Exchange went pretty smooth with only a couple issues that required some minor troubleshooting. The most common swing method usually involves joining a temp server to an existing domain, running dcpromo on the temp server, disconnecting and then seizing all the active directory roles. The temp server is then used to transfer active directory to the final destination server. There's more than 1 way to migrate from Server 2000 to SBS 2008. In my case, here's an overview of what worked for me.
This migration method uses 2 virtual machines and Windows Server 2008 Standard install media. Using your virtualization software of choice, create virtual machines for a Windows 2000 server (configure same number of processors as the source 2000 server for HAL compatibility) and a Windows 2008 server. A Windows 7 loaded laptop running VMWARE Workstation is what was used for the virtual machines in this overview.
- Load the designated Server OS's (2000 and 2008) on the newly created virtual machines and configure the virtual network cards in bridge mode.
- Install, configure Windows 2000 with the same name and IP address of the source production server.
- Add static IP to the Windows 2008 virtual machine which will eventually be used as the source server for the SBS 2008 migration (I used Windows Server 2008 Standard VLM media which provides a 3 day grace activation period).
Prep the source 2000 domain controller as in Part 1
- Raise Domain Functional level of your Windows 2000 server to Native 2000
- Insert SBS 2008 setup DVD into your Windows 2000 server dvd-drive
- Run adprep /forestprep and adprep /domainprep from the Sources\Adrep directory
- Make sure the Windows 2000 domain administrator account meets the SBS 2008 password complexity requirements
Password must satisfy three of the following four categories.
- Minimum 8 characters
- Upper case lower case
- Numerals (0 through 9)
- At least 1 non-alphanumeric character
On the source Windows 2000 Server
- Run system state backup
- Restore backup to virtual Windows 2000 Server machine, reboot
- Login, review and verify restored active directory data
- Point DNS on Windows Server 2008 virtual machine to restored domain controller IP address then join domain, reboot
- Login, run dcpromo on Windows Server 2008 machine, reboot
- Login to Windows Server 2008 domain controller
- Configure DNS IP address on Windows Server 2008 to point back to it self
- Transfer all active directory FSMO roles to Windows Server 2008
- Configure Windows 2000 domain controller DNS to point to Windows 2008 domain controller
- Run dcpromo on Windows 2000 domain controller, shutdown Server 2000 virtual machine
At this point the migration to Small Business Server 2008 using your pre-filled answer file and removable device on the destination server should be straightforward. The laptop with virtual Windows 2008 server machine was assigned a static IP and designated as the default gateway in the answer file. Also make sure to raise the domain functional level on the virtual Windows 2008 domain controller to Windows Server 2003 from Windows 2000 Native.
The laptop and destination server were both connected to a separate standalone network switch (you could probably use a crossover cable as well). The migration to Small Business Server 2008 from the virtual Windows 2008 Standard domain controller ran successfully with all active directory FSMO roles automatically transferred. Active directory was uninstalled from the temp domain controller and the virtual machine shutdown.
The cutover to the new SBS 2008 server involved shutting down all the workstations, disconnecting the production server then connecting the new server to the network. It was literally a swap of the network cables from the standalone network switch to the production switch. The workstations were powered back on and the login access to the new server tested successfully. The old 2000 server was demoted while disconnected from the production network and rejoined back to the domain as a member server to preserve access to some legacy apps and to be able migrate all the current static data to the new server.
Comments or questions welcomed.














"Wow, that was painless" was my initial reaction after installing Sunbelt's Vipre Enterprise, configuring policies and deploying a few agents. I'm currently running Vipre and Symantec Endpoint simultaneously on the same network. It's a small Microsoft Windows based network with less than 15 users. The desktops are a mix of Vista and XP with Vipre agents running on a few of the XP machines. Before I continue with any details, here's some background leading up to this first impressions Vipre and Endpoint comparison review. 


