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I have update KB2852386 installed so that I can cleanup old update files. I have a 30gb SSD which has absolutely NO space left on it. I want to cleanup my winsxs folder (21GB), but the option in disk cleanup to remove old update files is not present. In fact, disk cleanup does next to nothing to do anything for me. I know that I cannot delete winsxs (duh), and I also know that the displayed file size is not "actual". I still would like to know why I cannot choose to clean old update files from disk cleanup.

Windows 7 Ultimate 64

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If the option is not shown, you already removed all possible updates. In this case you can't do any more cleanup. There is an 3rd party tool which claims to a much more deeper cleanup, but you have to pay to get it. So I have no idea how good it is.