S/MIME seems better supported than pgp for email use. it's built-in to the new mac mail app, thunderbird(for all three OS), a firefox plugin for gmail, OE, and Outlook. There are plugins for many other apps, like Eudora(some support?), Mulberry, and Lotus Notes(built in?).
PGP is more often done with a plug-in. I also like the web of trust better in S/MIME. SSL certs are a well established way of showing you are who you say you are. The disadvantage is you more often have to pay for the SSL cert. Get free a one at comando.net
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