On May 20, 2007, at 5:34 PM, Jon Warms wrote: > Here's the first question: Does File>Save delete the old file in a > secure way, or does it just delete the old file, then reuse part or > all or none of that space as Finder sees fit, which could leave > some or all of the old file deleted insecurely? The latter. Your files essentially exist in two segments: the series of blocks on your hard drive where it is stored, and a directory pointer that says that "file XYZ is in blocks NNN through NNN". Many file operations don't touch the blocks themselves, just the pointer -- so when you insecurely trash a file, the blocks still hold the data, but there's no longer a way of getting there. When you save a file over an existing file, you're doing two things: storing your data to a series of blocks, and changing the pointer to the new series. This *might* overwrite the old data -- and it might not. In general, the application just tells the disk system, "Save this -- I don't care how", and the disk system says, "Hmmm, what's the best way of doing this?" Leftover blocks will eventually be overwritten by other disk activity, but that could be any time between dinnertime and the heat death of the universe. Making your job even more fun, Microsoft software is even more fun for these purposes, since it creates new files to manage fast saves and temporary data storage. Also, some very intelligent people have come up with methods of recovering data that's been overwritten a few times. What I tell my clients who are concerned about this: most of these data recovery methods require physical access to the hard drive for lengthy periods of time. Therefore, you only need to take extreme measures with data that needs to stay secure if the computer is stolen. 99 times out of 100, you're safe if you store these documents to an encrypted disk image -- it's possible that some data might be stored in the clear elsewhere, but it's unlikely. Best, Jeff