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Windows Server 2008 R2 Disc Cleanup not deleting windows update files

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My C drive is out of space due to 35.6 GB (out of 39.9 GB) being taken up in the Windows directory. Within that the winsxs is taking up 23.2 GB. When I run the cleanmgr as administrator it finds just over 9 GB of windows update files that can be cleaned up. However, when I choose to delete those files they are not actually deleted. It just keeps finding the same files over and over even after multiple reboots. I ran the disc cleanup when I have just over 600 MB available, although I am loosing space quickly. I realize I cannot just delete the whole winsxs directory. But how can I tell which files are safe to delete, which ones would disc cleanup be deleting if it actually worked? (I have a second drive with plenty of space.)

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