In-place upgrade from Windows Server Standard to Enterprise or Datacenter

windows-server-2008

We ran into a little issue where Windows Server Standard only supports 32 GB of memory, which is depressing to find out when your server was recently upgraded to 48 awesome GB of memory.

Is it possible to do an in-place upgrade from Windows Server Standard (max 32 GB memory support) to Windows Server Enterprise or Datacenter (max 2TB memory support)?

I tried kicking off the Windows Server 2008 setup.exe from within the OS, which gives me an "upgrade" option.. but when I get to the "Where do you want to install Windows" part of the process, it tells me

The partition you selected might contain files from a previous Windows installation. If it does, these files and folders will be moved to a folder named Windows.old. You will be able to access the information in Windows.old, but you will not be able to use your previous versions of Windows

That's… not… what I had in mind when I clicked "upgrade"!

I really don't want to deal with a clean OS install on our production database sever, and would much rather do an upgrade install if at all possible!

Best Answer

I fired up a VM with Windows 2008 Standard on it, and then upgraded it to Enterprise. At first I couldn't because I didn't have enough disk space available on the C drive. It appears that 15-20 Gigs of free space is required. Once I made the C drive larger it upgraded without issue.

When there wasn't enough space it wouldn't upgrade and would require that I install a new OS much like you said you saw.

After I clicked upgrade, the installer confirmed that I wanted to upgrade then it started the upgrade. It's still running at the moment, but I'm sure it'll finish eventually.