Posted by on Jan 28, 2009 in General | 0 comments

SBS 2008 Migration

Two things:

1)     I’m going to try to blog more often.
2)    I did my first SBS 2003 to SBS 2008 migration this weekend.

I have done several SBS migrations in the last couple of years.  Migrating from SBS 2000 to 2003 was Painful (with a capital P and that rhymes with T and that stands for Tool…oh, wait.  Reverse that.  Anyway, back to our regularly scheduled program).  Migrating from SBS 2003 to SBS 2003 was either very painful  (if you following Microsoft’s instructions) or somewhat painful and more long winded (if you followed the very excellent instructions from the fine people at

While Microsoft hasn’t hit it out of the park with the SBS 2003 to SBS 2008 migration document , it is certainly easier than any other process they put together.  That being said, it still took the better part of a weekend to move less than 100 gigabytes of data plus the associated Active Directory (AD) information from one machine to another while using gigabit Ethernet!  Some items to be aware of if/when you have to do this:

  1. While the Exchange 2003 to Exchange 2007 migration is so much easier, it still takes a long time, especially if you have users who hold on to every email they have ever received.
  2. I wish there was a much easier way to forklift the shares from one server to another (with all permissions intact)…especially if you don’t have any shares that have special permissions (like only a subset of employees can access that share, which tends to be true in a small office).  Why you can’t just point a wizard at the old server and have it create a similar share on the new server with the documents is beyond me, since presumably the new server knows the AD rights for every user.
  3. I like the old SBS 2003 console SO much better than the new 2008 console.
  4. There is going to be a tsunami of issues with running a 64-bit OS print server with primarily 32-bit clients.  I already had to jump through hoops to get an HP printer to load both sets of drivers (hint…open up the Printers folder on the server from a 32-bit client, and then from File/Server Properties install the 32-bit server), and I have a Minolta printer that just doesn’t want to play along at all.
  5. Having 21 days to finish the migration is both a blessing and a curse.  I suspect I will be running to the wire.
  6. Why robocopy hasn’t been built into every version of the Windows OS since it came out is beyond me.
  7. Don’t bother having it look for updates on install, as it will just fail and require that you look for updates after.  Plus, doing that extends the “sitting around” time at the beginning of the process.
  8. The POP3 Connector is not any where near the Exchange Management Console.  It is under the Network Connectors portion of the SBS Console.
  9. If you had My Documents redirection set up on the old server, you will get false “offline” warnings on the clients.  Still trying to work this one out.

I’m sure there will be additional issues that will crop up…stay tuned.