source: https://support.appliedi.net/kb/a110/how-to-enable-the-disk-cleanup-tool-on-windows-server-2008-r2.aspx
How to enable the Disk Cleanup tool:
1) Go to Programs & Features, and in the Features section, enable/install “Desktop Experience”. The downside to this is that you will need to reboot your server after installing this and it installs other components you do not need on a server.
2) [RECOMMENDED] – All you really need to do is copy some files that are already located on your server into specific system folders, as described at http://technet.microsoft.com/en-us/library/ff630161(WS.10).aspx
The location of the files you need to copy depend on your version of Windows:
| Operating System | Architecture | File Location |
| Windows Server 2008 R2 | 64-bit | C:\Windows\winsxs\amd64_microsoft-windows-cleanmgr_31bf3856ad364e35_6.1.7600.16385_none_c9392808773cd7da\cleanmgr.exe |
| Windows Server 2008 R2 | 64-bit | C:\Windows\winsxs\amd64_microsoft-windows-cleanmgr.resources_31bf3856ad364e35_6.1.7600.16385_en-us_b9cb6194b257cc63\cleanmgr.exe.mui |
| Windows Server 2008 | 64-bit | C:\Windows\winsxs\amd64_microsoft-windows-cleanmgr.resources_31bf3856ad364e35_6.0.6001.18000_en-us_b9f50b71510436f2\cleanmgr.exe.mui |
| Windows Server 2008 | 64-bit | C:\Windows\winsxs\amd64_microsoft-windows-cleanmgr_31bf3856ad364e35_6.0.6001.18000_none_c962d1e515e94269\cleanmgr.exe.mui |
| Windows Server 2008 | 32-bit | C:\Windows\winsxs\x86_microsoft-windows-cleanmgr.resources_31bf3856ad364e35_6.0.6001.18000_en-us_5dd66fed98a6c5bc\cleanmgr.exe.mui |
| Windows Server 2008 | 32-bit | C:\Windows\winsxs\x86_microsoft-windows-cleanmgr_31bf3856ad364e35_6.0.6001.18000_none_6d4436615d8bd133\cleanmgr.exe |
Windows Server 2012:
C:\Windows\WinSxS\amd64_microsoft-windows-cleanmgr_31bf3856ad364e35_6.2.9200.16384_none_c60dddc5e750072a\cleanmgr.exe
C:\Windows\WinSxS\amd64_microsoft-windows-cleanmgr.resources_31bf3856ad364e35_6.2.9200.16384_en-us_b6a01752226afbb3\cleanmgr.exe.mui
Windows Server 2012 R2: must install Desktop Experience. Use Powershell command:
Install-WindowsFeature Desktop-Experience
Once you’ve located the files move them to the following locations (Server 2012 non-R2 and earlier):
- Copy Cleanmgr.exe to %systemroot%\System32.
- Copy Cleanmgr.exe.mui to %systemroot%\System32\en-US.
You can now launch the Disk cleanup tool by running Cleanmgr.exe from the command prompt.
If an old cleanup manager is used, windows update files will not be cleaned. For this you need Microsoft hotfix 2852386