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I need to be able to email a very sensitive file. I don't want any one without a password to be able to see anything in it.

Is there a free program out there that will do a really good encryption based on a password and then let me email it and pass on the password (by voice) so that it can be decrypted on the other side?

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5 Answers 5

up vote 6 down vote accepted

Use 7-Zip to encrypt into a zip file, using AES encryption, and you're all set.

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This method does not use private/public key pairs and cannot give assurance of true authorship of the encrypted files. PGP would be a better solution. –  kzh Oct 6 '10 at 16:21
But far too complicated for the ordinary user. :o( –  Iain Oct 26 '10 at 9:54

You can use PGP to encrypt your mail and you can add a signature. It's a everyday plus !

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Truecrypt is my favourite way of encrypting sensitive data. As well as encrypting files, it can also encrypt drives (perfect for carrying stuff around on a USB stick). The program works on Windows, Mac and Linux too.

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PGP is one of the best methods to do this. It is more assured that the intended recipient and only the intended recipient can read your file. This will require them to generate a private and public key pair. This is what makes PGP a pretty good privacy measure. They just give you the public key in which you encrypt the file with. Nobody but the owner of the private can decrypt the file.

For scenarios like yours is why PGP was created.

A good implementation of OpenPGP is GNU Privacy Guard (gpg). If you have gpg installed and you really just want basic encryption without worrying about the extra security of public and private key pairs, you could use gpg to just password protect a file:

$ gpg -c myfile

And to decrypt this file:

$ gpg myfile.gpg
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Sophos Free Encryption is what we use at work.

The recipient will need to install it too.

It can create self extracting exe files but you may have trouble sending exe via email

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