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Is there program (preferably free one) that can erase contents of C:\Documents and Settings\<username>\Local Settings\Temporary Internet Files\Content.IE5\index.dat file in secure mode - overwrite with multiple passes?

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PGP Desktop (there is a free version as well as commercial versions) can be used to securely delete files. In addition, the "Professional" (or "Business") versions of Windows have a cmdline tool (cipher) that includes a freespace wipe option. If you use the latter, you will need to first delete the file (do Shift-Del to bypass the Recycle Bin), then overwrite freespace on the selected volume using cipher.

There are various other "wiping" tools, including open source, though I'm only familiar w/ the applications above.

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Make a Windows UBCD cd, boot from it then use "eraser" to overwrite the files.

http://www.ubcd4win.com/contents.htm

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