All (and Benny),

Yes, I DO have multiple S/MIME certificates for the same address as there are some valid reasons for that. As my signature says, I am a CAcert Assurer. That organization issues Class 3 certificates where your identity is very carefully validated through face-to-face inspection of identity documents my multiple Assurers. Unfortunately, though, the organization's root certificates are not yet automatically included in any operating systems or browsers. Their certificates must be manually installed and marked as trusted before certificates issued by the CA will be recognized as trusted. Because of this, their use is currently limited to more technical and other security-minded individuals.

StartSSL's root certificates ARE, however, included with all operating systems and browsers, making them much more useful when communicating with less technical individuals. Unfortunately, though, the organization only indirectly vets a person's identity and only offers Class 2 certificates. While these certificate are just as useful for signing and encrypting messages, the recipient of the message cannot have the same confidence in your own identity as when using CAcert certificates.

I have also created my own CA and issue very limited certificates on it using OpenSSL. I use these such certificates only when communicating with certain very specific individuals.

Ideally, I would like to see MailMate have a combo box for both S/MIME and OpenPGP whereby the sender could select any certificate desired. While one might think that only a very few MaleMate users might have need of it, yet I think that it would be both a useful feature to advertise and that it fits in very well with the type of user that Benny has been targeting since the first versions of MailMate.

--
Scott Blystone
Rochester, NY, US

CAcert Assurer (see http://www.cacert.org)
StartSSL Notary (see http://www.startssl.org)

Note: This address also works for instant messaging.
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