at Wednesday, October 02, 2002 3:13 AM, Peter Gutmann
<[EMAIL PROTECTED]> was seen to say:
> As opposed to more conventional encryption, where you're protecting
> nothing at any point along the chain, because 99.99% of the user base
> can't/won't use it.
That is a different problem. if you assume that relying on every hop
between you and your correspondent to be protected by TLS *and* the
owner of that server to be trustworthy (not only in the normal sense,
but resistant to legal pressure, warrants from LEAs and financial
"incentives" from your competitors) then you are in for a rude awakening
at some point.

S/Mime isn't wonderful, but it is built-in to the M$oft email packages
and you can trivially generate a key *for* your correspondents to be
delivered to them out-of-band. installing is double-clicking a file, and
decryption automatic.  More security aware users will obviously want
their own, a key from a recognised CA or prefer pgp, but that is
upgrades to the basic security you can provide by five minutes work with
a copy of OpenSSL.

> In any case most email is point-to-point, which
> means you are protecting the entire chain (that is, if I send you
> mail it may go through a few internal machines here or there, but
> once it hits the WAN it's straight from my gateway to yours).
Depends on the setup. Few home users can afford always-up connections,
and most dialup ranges are blocked from direct delivery anyhow. the
typical chain goes
Sender-->Sender's ISP-->Recipient's ISP-->Mailspool-->Recipient

for a corporate user, a typical chain might go

Sender-->sender's internal email system-->sender's outbound
gateway-->recipient's firewall-->recipients inbound
gateway-->recipient's email system-->recipient

assuming *everyone* at both companies is trustworthy (or IT is on the
ball and preventing sniffers from running on their lans; I will pause
while everyone laughs and then drafts replies pointing out that is
impossible) then you can get away with TLS-protecting just the link
gateway-->firewall.
Yes, crypto should be transparent and enabled *by default* in those M$
corporate products; no, the US government wasn't (and still isn't even
under the more relaxed regime) willing to wear on-by-default
unbreakable, easy crypto in mass-market products.

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