I have run into this issue several times and thought to write a post for it: http://social.technet.microsoft.com/wiki/contents/articles/15221.enabling-disk-cleanup-utility-in-windows-server-2012.aspx What you need to install is feature: Desktop Experience This can also be done with PowerShell 1.0: Add-WindowsFeature -Name Desktop-Experience In PowerShell 2.0, you first have to import the appropriate module manually: Import-Module ServerManager Add-WindowsFeature -Name Desktop-Experience Then you can search for Disk Cleanup, and cleanup system installation files by following these steps: Open Disk Cleanup by clicking the Start button In the search box, type Disk Cleanup , and then, in the list of results, click Disk Cleanup . If you're prompted to choose a drive, click the drive you just installed Windows on, and then click OK . In the Disk Cleanup dialog box, on the Disk Cleanup tab, click Clea...