> I fully agree. The state of TLS in the mail world is quite sad and it
> would be great if we could all agree on actually keeping our systems up
> to date... 

TLS in MUA protocols (IMAP or whatever Microsoft calls MAPI this week)
is fine.  Not sad.

TLS in SMTP mail is also not sad; it's fundamentally broken because of
the lack of a well-agreed binding between "who I am talking to" and
"what certificate I should expect," with a dip into "and by the way I
got all this information out of DNS which is also not very trustable"
along the way.  Sad would be an upgrade for this stuff.

And even if there were some HSTS-like way to bind certificates to
destination domain names, the lack of an interactive moment for the user
to say "yes" or "no" to a questionable certificate makes it even worse.

TLS in SMTP mail is weak opportunistic encryption, which is A Good Thing
but the reign of the crypto woke-purists who insist that the TLS must be
secure against all known attacks is more than a little annoying when
everything surrounding the actual moment of key agreement & algorithm
choice is not very secure.

Yes, it would be nice if everyone were running newer versions of TLS.
And yes, I understand it's hard to have a TLS library that can tell the
difference between a user sending mail and a user going to a web site,
yes, I get it.

But large production email systems have a lot of moving parts in
addition to the actual hard work of keeping the mail stored and
accessible: SMTP gateways, TLS off-loaders, load balancers, and of
course everything has to work with everything else (and every domain
name and TCP port number that was ever handed out by customer service
since 1994) and every client except for Eudora because we've given up on
Eudora finally but G-d WILL strike you down if Pine stops working so
don't forget to test that.

Yes, we'll get all those systems upgraded.  But I'm tired of having
folks who should have gotten their frickin' stuff right the first time
creating crisis after crisis in software updates and patching every time
someone with facial dermatitis steps up to the podium at Black Hat.
There's a whole lot of tail-wagging-the-dog here from the point of view
of the world of email...

Rant off.

jms


-- 
Joel M Snyder, 1404 East Lind Road, Tucson, AZ, 85719
Senior Partner, Opus One       Phone: +1 520 324 0494
j...@opus1.com                http://www.opus1.com/jms
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