> That doesn't sound as if you were a friend of these. Since I saw a few
> using S/MIME in this list, what might have been their reason? Is
> S/MIME better established with non-free software?

We had a discussion in February about this. Check out Jeremy's excellent
posts:

http://marc.theaimsgroup.com/?l=mutt-users&m=101258931506891&w=2
http://marc.theaimsgroup.com/?l=mutt-users&m=101260020607114&w=2

and, in the interest of equal time, Will's counterpoint:

http://marc.theaimsgroup.com/?l=mutt-users&m=101260114609607&w=2

Some excerpts from Jeremy's messages:

    S/MIME does not use keyservers like OpenPGP does.  It also does not have
    a web of trust concept, instead relying on central CAs.  They consider
    this an advantage, since it means you can always verify a message
    regardless of your current network connection status, etc... all that
    you need to verify the message is containted in the message itself and
    your local list of trusted CA certs.
    
    [...]

    The difficulty of PGP is what's kept it from being publically accepted
    as a normal thing to do [...] People need to accept encryption the way
    they accept envelopes on snail mail.  They never would have globally
    accepted these if you couldn't use one unless you knew how to make your
    own adhesive, ink, and stamps. 

    I saw Phil Zimmerman speak a few months ago at ALS in Oakland, and he
    understands this more than anyone.  He expressed a good bit of dismay at
    how clique-ish PGP usage is, and how much it has missed the mark of
    being a way to give encryption to the masses and make it normal.  He
    endured all manner of government harassment to defend people's right to
    use this stuff, and yet years later, hardly anyone is taking advantage
    of it.

    It was really interesting hearing him speak.  It's too bad he had to
    stop due to people in the audience arguing that there was no value at
    all in people using PGP unless they all used it completely securely (the
    main antagonist noted that he keeps his private keys on a CD and never
    has that near his computer unless it's completely disconnected from the
    network), which prompted a bunch more people to complain that there was
    too much talking and not enough key signing going on.

So my summary point is that the mailers designed "for the masses" are
choosing S/MIME instead of PGP because PGP's trust model is too complicated
for, say, my mother to understand. Look in the PGP manual under, for
example, "--edit-key". All kinds of complicated trust issues, with phrases
like, "the signature is marked as non-exportable", "this updates the
trust-db", "add a subkey to this key", "marginally trusted" "fully trusted",
"ultimately trusted" ... I have no idea what most of that means, and no
amount of UI design is going to help that. Will Outlook pop up a message
which asks Joe AOL User, "Do you marginally trust this, or ultimately trust
it?" Joe doesn't understand the security issues.

With S/MIME, the only question is, "Do you trust [company] to certify that
people are who they say they are?" Assuming Joe does, everything else is
completely automatic.


-- 
Mike Schiraldi
VeriSign Applied Research

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