1) - i think this will depend on if you are talking 32 or 64 bit versions, i have a similar job of going from 2003 x86 to a 2008R2 x64 and most info you find on the internet (even on technet) doesn't mention that a x86 printer driver isn't going to work on x64. Sounds obvious but that one of the hardest part of doing the conversion. I think the best method is to add the x64 drivers to the 2003 print server, then on the 2008 install the print management role, you should be then able to add another print server to the print management console (i'm not positive in 2008 but its possible in 2008R2), after that you can right-click the 2003 print server in the 2008 Console and select export - which will save all the settings to a file, then you right click your 2008 print server in the console and import. I don't think it will import permisssions but you might need to report on that - i am curious on it. Personally i would assign printers by Security groups so that its very simple to reapply permissions if necessary. 2) - use the robocopy tool (built in with 2008), you can read up on all the switches, but i think you want is something like /copyall or /DATSOU, these might be wrong so read up on the right switches. There also exists a few GUI front-ends for robocopy which is why i don't remember the switch. BTW - both servers need to be in AD for this to work. I suggest testing before a real migration.