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Would you know of a reason why disk cleanup would skip compressing old files...?
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Whatever you tried to say there, it's got me completely confused over the use of terms that, for me, have absolutely no relationship at all between them, or with the main topic.
Are you talking about the Disk Cleanup feature of Windows XP? I can't help you with the tool itself, but (unless someone corrects me on this) I can tell you that it's probably shit (judging on the quality of Windows XP's bundled software), so avoid it. If you want to clean up your disk, delete files (not system files!), or backup onto another device (either hard drive or CD/DVD).