[Discuss] Running a mail server, or not

[epp at linuxmail.org]

On 06/27/2018 03:39 PM, discuss-request at blu.org wrote:
> On 6/27/2018 1:58 PM, Rich Braun wrote:
>> I don't see how we're in disagreement here. Naturally, if you send to
>> a listserv like blu.org, there will be multiple hops (most likely but
>> not guaranteed to be encrypted). But if you send directly from your
>> email to mine, your system will connect to easydns (in Canada), which
>> will attempt STARTTLS but not guarantee it; once it's queued at
>> easydns, then it's encrypted as it gets to my private installation. I
> Operative words: "but not guarantee it". This contradicts the assertion
> that, "[t]here is no clear text SMTP on the wire." In reality there may
> be clear text SMTP on the wire.

I've noticed when e-mail comes into a Comcast address, the sending mail 
server (Yahoo/AOL (when it works), Gmail, mail.com, GMX, etc.), the 
receiving Comcast server receives it with SMTP. But when Comcast sends 
an e-mail out to one of these services, it sends with ESMTPS (secure). 
Why secure connections one-way and not both directions?

I have also noticed when sending through Yahoo/AOL (again, when it 
works), even though the Thunderbird settings are set to use SSL or 
STARTTLS, the receiving Yahoo server always receives it with SMTP. 
Server mis-configuration there?