Encrypting email - what is the best way?

[tankman1989]

I'd like to give employees access to webmail that automatically encrypts when it sends. It would also be great if the user could generate their own random data and passphrase, which is probably standard.

I know I can use enigmail which is the plugin for Thunderbird but that doesn't cover webmail.

Does anyone have any ideas?

[YeOldeStonecat]

If it's just for a single user to play around with...check out JumbleMe
http://www.jumbleme.com/video.aspx?video=sendinggmail
Works with any web mail client.

Hushmail.com is another decent freebie for single users.