[OTR-users] options for encrypted file transfers

[Jason Cohen]

If you want to encrypt file transfers you have a few options.

a) Use a silc client and initiate a direct key exchange. As long as one
user isn't behind a NAT this will allow you to initiate an encrypted
peer to peer connection using DH exchange and all file transfers will be
encrypted. You can use gaim & gaim-silc or silky or silcclient.

b) use a VPN. I would suggest openvpn.net. It's extremely easy to setup
especially if you use preshared keys rather than (more secure) private
key + certificate authentication. This will create a virtual tunnel
between your machines, and all traffic will be encrypted &
authenticated. Diffie Hellman is used to create the encrypted session
and you use a private key & public certificate (which has been signed by
the VPN server's Certificate Authority) to authenticate.

c) This is probably the most common. Use OpenPGP and  encrypt the body
of the email + the attachments with PGP/MIME prefferably or PGP/Inline
if you must. Your friend will need to send you his public PGP key.