the issue: cleanmgr.exe (Disk Cleanup) is not present in Windows Server 2008 or Windows Server 2008 R2. truth is, it’s just not available by default. per microsoft this is by design, as the Disk Cleanup button is part of the Desktop Experience feature – therefore in order to have Disk Cleanup button appear on a disk’s Properties dialog, you will need to install the Desktop Experience feature.

here’s how to get it: copy two files that are already present on the server, cleanmgr.exe and cleanmgr.exe.mui:

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
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:

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

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