Today, I learned that if you want to run Disk Clean up in Windows 2008 R2, you have to actually install the feature called Desktop Experience. Launch Server Manager, click on Add Feature, and check Desktop Experience. Disk Cleanup is not installed by default. Who knew?
After a restart, you can access Disk Cleanup via Start > All Programs > Accessories > System Tools.
These are the kind of screw ups that give MS a bad name. No Admin is going to put desktop experience on a server but because of the idiotic way patches build up over time you HAVE to have disk cleanup to clear them off. How could no one have seen this
would be a problem when it was built