I’m using Windows Server 2008 R2 64-bit.

However, cleanmgr.exe cannot be launched directly using Win+R.

Copy the file in the path below to %systemroot%\System32.

C:\Windows\winsxs\amd64_microsoft-windows-cleanmgr_31bf3856ad364e35_6.1.7600.16385_none_c9392808773cd7da\cleanmgr.exe

Copy the file in the path below to %systemroot%\System32\en-US.

C:\Windows\winsxs\amd64_microsoft-windows-cleanmgr.resources_31bf3856ad364e35_6.1.7600.16385_en-us_b9cb6194b257cc63\cleanmgr.exe.mui

Then cleanmgr.exe can be launched directly.

Further Reading

  1. 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 | Microsoft Docs

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