I just upgraded a server from Windows Server 2003 (with SP2 installed) to Windows Server 2003 R2 (SP2 slipstreamed).

It wasn’t exactly smooth, because I didn’t RTFM… (it’s my home server, it’s Saturday afternoon, it should have been trivial and I don’t have a lot of time to spend planning this… a perfect demonstration of the need for proper planning that I stress to my customers). If you want to avoid my cowboy IT guy approach (i.e. insert disk 1 and upgrade from running copy of Windows – what could possibly go wrong?), check out Microsoft knowledge base article 912309 before starting the job (I didn’t).

Because I didn’t do it properly, I had some issues but I imagine there are plenty of others who will try what I did and may now be googling to get out of a few holes. This is what I did – your problems may differ depending on your configuration:

• When my screen reverted to 4 bit 640×480 colour (but Device Manager said my display adapter was working fine), I ignored the problem. After a reboot, I was back to my usual display properties.
• My machine (which is a domain controller) complained that it couldn’t install the R2 components until I had updated the Active Directory schema. I followed the instructions (run opticaldrive:\cmpnents\r2\adprep\adprep.exe /forestprep) and then restarted R2 setup with opticaldrive:\r2auto.exe (I could also have used opticaldrive:\cmpnents\r2\setup2.exe).
• Changing directory permissions (that’s what adprep.exe did) will break certain applications – in my case WSUS and Virtual Server (i.e. those apps that rely on IIS). I’m still working on that issue and will blog something when (if) I fix it.
• The upgrade also wiped out at least one of the configuration changes that I made in the registry – in this case enabling IP forwarding.