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I need to e-mail a file to someone with whom I have already negotiated a password. What are reputable, reliable and open-source tool with simple UI? An example for disk (as opposed to file) encryption is TrueCrypt. Platform is windows but available linux port is a plus.

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Adam, once I see the good answer for my question I will up upvote it. So far I have not found a 'truecrypt for files' I am afraid. –  99CPU Feb 19 '10 at 10:52
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AxCrypt seems to be a good place to start from. Quoting its webpage:

AxCrypt is the leading open source file encryption software for Windows. It integrates seamlessly with Windows to compress, encrypt, decrypt, store, send and work with individual files.

If you want to add some nice spice into it, and you're exchanging these files on a regular basis, create an encrypted disk within a file with TrueCrypt and share it with your friend using dropbox. It will give you a flexible, seamless directory structure which is automatically encrypted and synchronized.

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Have you looked at GNU Privacy Guard?

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It should be a sinple thing to use: click-dowloaded-click-installed-click-password and file to encrypt - done. –  99CPU Feb 11 '10 at 13:04
    
@99CPU there are actually several GUIs for GPG. All of them provide a very simple way of using GPG. E.g. gpg4win.org –  Raffael Aug 27 '13 at 17:38
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7-Zip encrypts files and is also the best open-source file archiver.

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