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10.6: Sign and encrypt emails in Mail via thawte
It should be noted that the paranoia of Thawte retaining one's public key seems unwarranted. From what I understand, the public-private keypair is generated in the local browser, and only the public key ever travels over the wire. This is why you can only retrieve a certificate from the same computer, same user login, same browser, etc. Accordingly, the setup is much simpler than this.
I wrote up some instructions for this process some time ago: http://homepage.mac.com/quinntaylor/secure_email/smime.html I'll have to update them with the fact that 10.6 breaks MacGPG (I never liked PGP so much, anyway) and that Thawte is discontinuing the Freemail certificates. (They really should advertise that better, a lot of people are going to be caught unawares.) That's a real bummer.... Looks like Verisign is ~$20/year (1 year free for current Thawte cert holders) and Comodo is ~$12/year. (Couldn't find a free offer as someone mentioned.) Now I have to evaluate whether it's worth money for me to get a certificate... :-( By the way, people in other replies mentioned CACert and the OS X Certificate Assistant. The former is not a certificate that's trusted by default on OS X (and probably not on Windows, either) and the latter will work, but will use a self-signed certificate, which is a far cry from certificates issued by trusted authorities like Thawte and Verisign, which are already trusted by most operating systems. At least generating a self-signed certificate is free, despite the increased complexity of being trusted.
10.6: Sign and encrypt emails in Mail via thawte
Free Comodo certificates (via InstantSSL) are available here: http://www.instantssl.com/ssl-certificate-products/free-email-certificate.html
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