If you want to run the Disk Cleanup Wizzard (cleanmgr) on Windows 2008 Server you need to install the "Desktop Experience" Role and restart your computer.
So basically, start the Server Manager (CompMgmtLauncher.exe) - Features - Add Feature - Desktop Experience and restart your machine. IT doesn't mention this also adds the Cleanup Wizzard though, heh.
It's a bit counter-intuitive, but that's how it is. This also adds themes, Media Player, photo management and a few other useless things.
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