Thus said Lonnie Olson on Tue, 03 Jun 2014 10:13:07 -0600:

> Additionally, I  recommend enabling opportunistic SSL  on both inbound
> and outbound  SMTP connections  over port 25.  This will  encrypt even
> more SMTP traffic when possible, and is the good neighbor thing to do.

While  that might  sound secure,  shouldn't one  ask just  what this  is
protecting  against and  what are  the risks?  Are their  any SMTP  MTAs
(client side)  that require you  to verify  the fingerprint of  the SMTP
server to which it  relays email? Do they refuse to  deliver email if it
changes and  notify you that the  fingerprint is not what  was expected?
How many  SMTP servers use  untrusted certificate chains  vs self-signed
certificates?

Given the current  poor state of SMTP+SSL security,  what prevents those
in  the  middle  from  successfully executing  MITM  against  your  SMTP
server/client software?  (I am  not talking about  MUAs). Is  it perhaps
``good will'' or ``good faith?''

I will concede  that if the attacker  is passive then SSL  will at least
protect against passive sniffing, but if  they have the ability to get a
passive session,  then they are one  step removed from having  an active
session.

The  best way  to  ensure end-to-end  security in  email  is still  PGP.
Anything else is just security theatre.

Andy
-- 
TAI64 timestamp: 40000000538e896b



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