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I need to send several gigabytes of data to a client. My plan is to create a truecrypt-filesystem on a usbstick. However, truecrypt isn't very straight forward in use. And not all our clients are very tech savvy.

Are there any simpler, but still free and higrade encryption solutions out there?

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Does the solution need to be platform agnostic? –  MacLemon Apr 10 '10 at 17:52
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4 Answers

Use 7-Zip to create a self extractor and you set AES-256 encryption. then all they need do is double click on it, enter the password and choose where to extract the files. And for an added bonus they will be compressed. Using the new 7-Zip you will be able to use LZMA2 compression which might make it a bit smaller.

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Extracting the files to an unencrypted file system may defeat the purpose of sending the files encrypted. Of course the security requirements may not be that harsh, or you might be using full disk encryption on the receiving computer, in which case this works just fine. But it's worth thinking about that too. –  Peter Bagnall Aug 27 '12 at 22:38
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I went with TrueCrypt anyway. It has some nice command-line features that makes it easier. Only problem is that one needs administrative access to start it... I made a .bat file that only asks for the password, and then mounts the drive.

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This is probably the best solution if security is paramount. –  Peter Bagnall Aug 27 '12 at 22:39
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I'm not sure how strong you want your encryption to be. But maybe an encrypted archive (rar/winzip/7zip) is an option for you. The howto of extracting such archive files is well known, and easy to explain if needed. There would be even an option to make it self extracting.

The latest version of RAR would be RAR3 which supports AES encryption with 128 bit key length for example. File data aswell as the headers will be encrypted.

This way does give up security for ease of use, but it's still rather hard to "crack" such an protected archive. But do be aware of password crackers that are designed to brute passwords on such archives...

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If your clients use Linux & Gnome, you can just put a LUKS encrypted partition on the USB key, and a password prompt will pop up when they insert it.

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