At a security level, the main complaint with S/MIME is that someone can 
send you a 40-bit encrypted message and you can do nothing to stop them 
from doing so. Nor can you easily tell when someone has used a weak key.

Yes, S/MIME supports larger symmetric key sizes but it also has backward 
compatibility for the smaller and weaker key sizes.

   --Noah--


On Friday, March 22, 2002, at 12:22  PM, Garbrecht, Frederick wrote:

>
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> I apologize if this is a hopelessly stupid question, but I don't
> really understand the relative merits of using PGP for email
> authentication & encryption versus using Microsoft's implementation
> of s/mime and digital signatures.  I run a small windows network and
> would like to begin offering my users some way to authenticate (and
> if necessary encrypt) their email.  Since we use Outlook pretty
> uniformly and Exchange Server, it would seem logical to use the built
> in capabilites these products have to provide security.  Is there a
> reason not to do this and use a third party product ala PGP instead?
> I assume the answer has at least partly something to do with the MS
> tendency to avoid cross-platform compatibility by not implementing
> stuff completely in accord with standards (like they've done with
> ipsec), but I'd be interested in hearing from the experts.
> Thanks
> Fred
>
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