The latest release of Microsoft's highly acclaimed Small Business Server is upon us and many of our customers are asking, "when do I upgrade?" The simple answer is to wait it out unless you already are in need of a new server. SBS 2008 does have many easier management features, nice wizards, great reports, and Exchange 2007. However it does have a sharp migration curve, needs a very beefy (only 64 bit) server, and still has it's bugs and quirks. Microsoft's official migration guide from SBS 2003 to SBS 2008 is not as straightforward as it seems. Many items are misworded or simply nonexistent.

Also of particular interest is that if you have SBS 2003 later than SP1 and never installed SP1, when you install SBS 2008 and begin migration it will tell you that SP1 is needed on the source server. Yes, even if you have a later release it stills looks for older. You can quickly hack the registry on the source server to get around this and it will move right along. However, as mentioned, definitely not straightforward. As always with any migration, plan, plan, plan, and then plan some more! Make sure all users versions of Outlook will work with Exchange 2007. Make sure all the software you plan to migrate is going to work on Windows Server 2008. Lastly, make sure everyone understands there will be road blocks. As with most Microsoft releases, if you can wait for one or two service packs, let everyone else hit the speed bumps first and then jump in.