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Like a shell extension or something so that when I or a co-worker copy over a file we know why we copied it.

Something like source control for binary files, but totally non-restrictive.

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I was just posting this in another thread.

Have a look at HOBComment Shell Extension and Explorer Extension, it allows you to add a comment to files via a shell extension.

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Note: this only works for NTFS formatted volumes, if you copy the files to a drive with any other file system (e.g. FAT32) you will be prompted to "confirm stream loss", the file will be OK, however, the attached comment will be lost.

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Not that I know of, or have ever heard of.

However, you may want to take a look at the auditing feature of the NTFS filing system.

Right click on a file or folder and go to the Security tab then click Advanced, go to the Auditing tab and basically set up the structure you want.

Anything that meets the rules you set up should be logged. I know this isn't exactly what you want, but it is the closest that I think you can do.

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