I recently attempted an SBS 2008 migration to new hardware. It didn’t go well, for a number of reasons.
Firstly, the server I was moving from was not working well. This was the main reason for the hardware migration attempt, but it also made actually getting the migration to succeed quite difficult. In this case, there was actually an NTFRS issue that was actually stopping the server from becoming a domain controller correctly, which was making the migration attempt when it tried to replicate the AD to the new SBS server. This is bad because it leaves the source AD with a half-installed domain controller that you need to get rid of. Plus, it takes about an hour or so to get to that point, so retries of the procedure are expensive.
Things I would recommend:
1. MAKE SURE THERE ARE NO OUTSTANDING ISSUES ON THE SOURCE SERVER. Run the SBS Best Practices Tool. Run the Microsoft IT Environment Health Scanner. Fix anything you find there. Check your event log for errors and fix them as well. Make sure you’ve got a clean, recent backup. (That one really should go without saying, and I’m lucky it didn’t apply to me in this case).
2. Follow the migration document. I did have an issue where the new Domain Admin user I created didn’t seem to have rights to check some things. Follow the advice, create a new domain admin, and test it for some domain operations before using it for the migration.
3. Don’t run the migration in unattended mode. This migration is quite fiddly and you need to be able to check what’s going on at different points. You’re going to be sitting there waiting for it to finish anyway, toughen up and do it manually.
4. I had issues with trying to install updates during the migration as well. Not sure how much they were related to the other issues, but personally I would prefer to play it safe, and do the updates afterwards. If necessary, you might need to disable the WSUS in the new server while you install, to prevent it auto-updating the install while it’s occurring. Just remember, do the updates before moving your inbound connections from the internet to the new server.