The issue: CCleaner always reports that there are 3,898 files in the Recycle Bin in addition to whatever files are actually in the Recycle Bin. These 3,898 files are not seen in the Recycle Bin when you browse to it through Explorer. This list has not changed over time; always the same exact files. Here's an example of one of the files that is reports: C:\$Recycle.Bin\S-1-5-[NUMBERS HERE]\$R0W99R7\Extravaganza\Extravaganza (1).JPG How did I fix this? I had to navigate to that folder in Explorer and do a SHIFT + DELETE on them (tried a script first but even though it reported itself as deleting the files, it actually didn't). CCleaner could see the files but it couldn't delete them. Now the files are actually gone after doing the SHIFT + DELETE on them and CCleaner no longer reports them.