In most cases - with smaller SBS environments it is generally easier and quicker to just replace the existing SBS 2003 domain with a new SBS 2008 and then integrate all the workstations and devices and data into the new network.
This customer was in a situation where due to the size of the network and the complexity of the application & database servers on the network (third party vendor installation and configuration, etc) switching to a new network was not the most cost effective option and we opted to attempt a migration using the Microsoft published SBS 2003 to SBS 2008 migration plan.
This was successful, but not without its challenges - the main stumbling blocks I encountered was to do with the preparation of the existing server.
The old server was deployed with ISA 2004 and was configured as a web-proxy and firewall for the network and the server had already been through a P2V conversion. So the actual migration took place within a Citrix XenServer hypervisor.
These are the steps I followed to get the migration done:
- Uninstalled ISA
- Removed any Anti-Virus and Spam filtering software.
- Removed any Disk optimising programs. e.g. Diskeeper.
- Removed any remote access or monitoring applications.
- Next we needed to manually remove the existing network configurations from the registry. http://garclak-kb.blogspot.com/2011/06/nic-configurations-in-registry_14.html
- Run the Connect to the Internet SBS wizard.
- Run CHKDSK on the system volume - if this results in the system repairing zillions of SID errors - you may need to adjust permissions in the System32 folder as some services will not start properly due to access denied errors.
- Applied the NTFRS registry fix to allow the system to repair the Journal Wrap condition.
- Ran DCDIAG and fixed any problems encountered.
- Ran the SBS 2003 BPA and resolved any problems
- Raised Domain and Forest functional levels
- Set Exchange to run in Native 2003 Mode.
- Checked the Administrator accounts - there should be a second account setup to replace the Administrator account post-migration. Check group memberships and set primary group to Domain Users.
- Apply any Windows Updates.
- Take a backup of the system once system is clean as a whistle.
- Install the Migration Preparation Wizard.
- Install the Migration Preparation Wizard Update. http://support.microsoft.com/KB/981802
- Run the Migration Preparation Tool and the server may need to be restarted to apply any changes, etc.
- Start the destination server in Migration Mode using the Answer file. You may need to copy this file manually into place if migration mode does not start automatically. Once complete check for any Installation issues - there should be no Red Crosses that indicate a critical problem with the migration process has been encountered. Assess the relevant migration logs and you may need restore the source server back to the last backup and resolve any additional issues before attempting the migration again.