Apart from the lack of native Oultook support, why should one prefer S/MIME over PGP/MIME for email?
From my (still quite subjective) point of view, GnuPG/PGP is superior to SSL (or more specifically, PGP/MIME over S/MIME; maybe in other areas SSL is the better choice), e.g. due to the support of ...
Analogously to the SSL server certificate question, which extensions should I use for S/MIME, and should the CA be restricted somehow as well? (I'm using openssl, which at the moment creates CA and ...