I have done a couple SBS 2003 to SBS 2008 migrations in the past and because the customers were relatively small with less than 20 users, we opted to just build the new SBS 2008 server with a completely new domain and then migrate the data. We would recreate all the user accounts, mailboxes, and shares and choose a maintenance window to do the switchover. It works fine for companies with low complexity and downtime flexibility. However, I just started an SBS 2003 to SBS 2008 migration for a company that operates pretty much 24-7 and they have a fairly high complexity level on the application side.

I have tried some of the SBS 2000 -> SBS 2003 migration tools and they were pretty pathetic, but I had to have an easier way for this migration. After some research, I came across a set of processes that you can use to migrate SBS 2003 -> SBS 2008. They are documented pretty well by Microsoft here: http://www.microsoft.com/downloads/details.aspx?FamilyID=52b7ea63-78af-4a96-811e-284f5c1de13b&displaylang=en.  The process is pretty tedious...I won’t get into it here. You can read the doc if you are interested.

The gotcha is what I encountered during the migration install. [more]When you provide the unattended install file for the SBS 2008 install, first it goes through and installs the OS. After a reboot, it starts the actual migration process. I was watching closely and noticed that it seemed to hang at about 20%. I looked at the event logs on both ends and couldn’t find anything then after some a search on Google I found a user blog that mentioned accessing the sbssetup.log file via file share during the install. I checked it out and it indicated that the new SBS server could not find a server in its AD site to replicate with. I reviewed AD sites and services and noticed that there was no subnet associated with the current default AD site. I added the subnet and waited a few minutes and the progress began to move forward…yeah success!

No so fast. It move about 10% and stalled again. Again after looking in the log file, it was an AD replication problem. This time the SBS 2003 server had a sysvol replication journal wrap problem. I found the MS article on how to fix it and applied the registry fix and restarted NTFRS. Again, progress.

The migration ran for another 3 hours and stopped about 95%. Another log reviewed showed the problem was DHCP related. I connected remotely to the DHCP service and I could see that the scope was getting created and the server options were set, but the reservations were not there. I started reviewing those thinking there might be something there holding it up. By accident, I found that one of the MAC addresses in one of the reservations had a trailing space following the MAC. I removed that reservation and after a short wait, the migration continued and finally finished….6 ½ hours later.

So two things. 1. Watch the log file 2. Get lucky