Disk Cleanup

Disk Cleanup option on drive’s general properties and cleanmgr.exe is not present in Windows Server 2008 or Windows Server 2008 R2 by default.

Applies To: Windows Server 2008, Windows Server 2008 R2

The Disk Cleanup executable file cleanmgr.exe and the associated Disk Cleanup button are not present in Windows Server® 2008 or in Windows Server® 2008 R2 by default.
Because:
This is by design, as the Disk Cleanup button is part of the Desktop Experience feature.
In order to have Disk Cleanup button appear on a disk’s Properties dialog, you will need to install the Desktop Experience feature.

Bypass resolution:
So in order to use cleanmgr.exe you’ll need to copy two files that are already present on the server, cleanmgr.exe and cleanmgr.exe.mui.
Use the following table to locate the files for your operating system.

Operating System                Architecture    File Location
Windows Server 2008 R2    64-bit            C:\Windows\winsxs\amd64_microsoft-windowscleanmgr_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

Once you’ve located the files move them to the following locations:

Cleanmgr.exe should go in %systemroot%\System32.
Cleanmgr.exe.mui should go in %systemroot%\System32\en-US.

You can now launch the Disk cleanup tool by running Cleanmgr.exe from the command prompt.
Disk Cleanup can now be run by entering Cleanmgr.exe into a command prompt, or by clicking Start and typing Cleanmgr into the Search bar.