How To Send Files Securely From Fedora

[Robert L Cochran]

I want to send files securely from my Fedora 11 (Preview) or Fedora 10 
systems to a Microsoft Windows (Home Edition) user who quickly gets lost 
if asked to do anything complex. By "securely" sending files, I mean I 
wish to attach files to an email and then send them over the wire either 
encrypted or password protected such that there is little possibility of 
anyone but the intended recipient being able to see the files in clear.

I would also like the user to be able to send files back to me which are 
similarly secured.

The user likes Windows Live Mail. I do not think the user capable of 
managing public keys or of understanding how to decrypt public-key based 
files unless it can be done with one or two mouse clicks. I could do the 
initial setup and testing myself. Everything has to be geared to 
allowing a quite basic user to view the cleartext quickly and very 
simply, without others on the Internet being able to crack it.

I've thought of sending password-protected zip files using the Fedora 
zip utility. Perhaps these are compatible with the same utility in 
Windows XP?

Any suggestions?

Bob