I recently completed a migration of Windows SBS2k3 to SBS2k8. In doing so, most of the process (while tedious) went smoothly. Who would have thought that printer deployment would be the big issue! Based on my experiences, I've come to the conclusion that the print manager in Windows 2008 is stupid at best. Let me explain:

• SBS2008 is a 64bit operating system. This causes complications because most client PC's are still 32bit. Not a HUGE deal, you should be able to just load the 32bit drivers by some easy mechanism on the server. No. The proper method is to log in on a client PC as an administrator (or person with the appropriate permissions to add printer drivers), then browse to the 'server' printer and faxes share. Right-click, server properties, add driver. That in itself doesn't sound difficult (and it's not). The kicker is the damn drivers must be the same version and type as what's installed for the 64bit operating system. In other words, use the printer manufacturer's drivers, not the OS included drivers. PCL 5 is not the same as PCL 5e--definitely not the same as PCL 6.
• The actual 'deployment' process involves Group Policies. That's actually very cool and powerful, but only works as advertised with Vista or Windows 7 clients. If you're using Windows XP, you must have CSE installed on the client AND you must deploy the printers using 'USER PREFERENCES, Control Panel Settings, Printers'. You cannot deploy them using the POLICY section (which is the default behavior in SBS2008's print manager).

After that, everything appears to work as advertised. In my opinion, this is one area where they SHOULD have a wizard. At the very least, the OS should support supported client OS's properly out of the box without special voodoo magic tricks. Like it or not Microsoft, XP is a supported operating system for 2008 Server. This should be simple stuff and should just freaking work. I'm not at all upset that I spent hours searching for answers online (finding nothing)