On 9/24/2013 2:28 AM, Reindl Harald wrote:

> maybe on your server, my logs showing the opposite and since
> the "smtp" are outgoing messages your conclusion of "nobody"
> is strange
> 
> cat maillog | grep smtp | grep -v smtpd | grep TLS | wc -l
> 12327
> 
> cat maillog | grep smtpd | grep TLS | wc -l
> 13350
> 
> cat maillog | grep smtp | grep -v smtpd | grep TLSv1.2 | wc -l
> 2603
> 
> cat maillog | grep smtpd | grep TLSv1.2 | wc -l
> 2219

This doesn't necessarily mean the encryption is effective at cloaking the data 
exchange.  Remember:

1) Most admins who use TLS on their MTAs don't reject the transaction of the 
presented certificates FAIL to be validated against your local trust store's 
certificates.  Unlike the error dialog boxes presented to the end user when a 
certificate fails to validate against its local trust store, these "error 
fallbacks" are "silent" and to most users, completely invisible. (Yes, I know 
most MTAs will log a TLS certificate failure in the headers, but we're talking 
about Lusers here, not readers of this list.)  Failing certificate validity 
means it could be ANYONE's key/cert used to setup the ephemeral connection, and 
you can place no reliance on that channel being opaque to third-party scrutiny.

2) Even if you DO reject all failing certifcate trust-stores (on *ALL* MX hosts 
that receive/send mail), it's increasingly likely that one or more of those 
root certificates are compromised, either publicly(*) or secretly though some 
back-door arrangement with the NSA.  The Big Ugly elephant in the room is the 
notion of the NSA having a certificate signing key for VeriSlime/GeoBust/et al 
so that they're free to use their own key + cert in a MITM interception, with 
the end user being none the wiser(**).  Take a tally of the jurisdictions of 
the big root-level CAs.  It's alarmingly AUSCANNZUKUS-centric.

3) Even with all of the above dealt with, the rush for people to use 
Diffie-Hellman "PFS" based on elliptic curves (EC) may be itself subject to 
additional problems based on revelations and leaks that suggest the NSA has 
been busy subverting various standards and publicly designed software reference 
implementations to weaken its security in ways to benefit them.  In particular, 
Schneier and Bernstein feel very uneasy about the NIST specified parametres for 
the EC-based cryptographic algorithms.  These aren't "tin foil hatters" or 
kooks.

To that end, there are proposals to adopt elliptic-curve parametres and methods 
that each and every generated public key maps to a valid EC point.

See:

https://www.schneier.com/blog/archives/2013/09/the_nsa_is_brea.html#c1675929
http://cr.yp.to/talks/2013.05.31/slides-dan+tanja-20130531-4x3.pdf
http://cr.yp.to/ecdh/curve25519-20060209.pdf
 
An Ivory Tower organisation with total control over the clients' and the 
servers' configurations can pin all of its certs + keys, and configure them to 
dump connections that fail to validate local trust stores.

This is an unfortunately very subtle and nuanced problem that defies mere 
"throwing more bits" at your key sizes. 

And I would hope that the IQ and worldly mindsets of those generally reading 
this list have an appreciation for why retaining complete control and privilege 
within your organisation's end-to-end security is important, now more than 
ever.  It has nothing to do with "I'm not doing anything wrong, so they can 
read all they want."

For an ISP or other provider with a "random" and "noisy" userbase with 
who-knows-what clients + OS/platform brain damage, the problem is probably 
intractable unless you accept that some users will be simply unable to access 
the services from some or all of their devices.

=R=

(*) Despite many compromised CAs (Certificate Authorities) being known 
publicly, I discover an annoying large number of improperly configured systems 
who accept these as valid. Maybe there are/were distros who incorrectly 
compiled lists of CAs and didn't remove those compromised CAs from the 
trust-store.  Maybe they're out of date.  Who knows why.

(**) If you "pin" various trust store certificates + keys, you can detect this 
when it occurs.

See: https://www.owasp.org/index.php/Certificate_and_Public_Key_Pinning

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