I want a colleague of mine to send me a sensitive Microsoft Word document via e-mail. Since Word's encryption is questionable, I would like to encrypt the file using a passphrase.
Do you know of any encryption method that a novice user can easily use? I wouldn't like to prompt for keys or anything like this - just provide a simple interface for single file encryption.
Answer
I have solved this using Putty Secure Copy, through a Linux box I have on the net. The user downloaded scp to the same directory where the file was, and I have send him the exact scp command by mail.
Kind of reversed the problem - using encrypted connection rather than encrypting the file. Of course, this solution might not fit everyone's needs - it works only if you have a trustworthy server.
But in second thought, one can always install a virtual machine, set the router to port-forward the ports and ask his novice friend to ssh to the virtual machine... But perhaps that's a rather long shot.
UPDATE
winscp works even better. It has simple and nice GUI that every novice user can handle.
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