The security of emails looks like it's getting some relief recently. There have been two interesting announcements recently. The first one came from Omniva securing USD 4 mio in series B.
The second one Voltage Security's has a pretty good PR department. Cnet and NYT feature an article about Voltage system. Although I couldn't identify Voltage's homepage.
Both systems should apparently be much more hassle free than former PKI. If they can really manage, at least they claim to), that encryption is transparent and 'encrypted recipients' and 'non-encrypted' are sorted out automatically, I will give both of them thumbs up. The will have a good chance to be bought by MS for Exchange 2003. (MS announced today, they will most likely run an extra dividend on its stocks to reduce free cash flow - amazing!)