[Discuss] Running a mail server, or not

[Richard Pieri]

On 6/27/2018 7:05 PM, epp at linuxmail.org wrote:
> 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?

My WAG? Comcast are logging all connections as SMTP regardless of
encryption.

> 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?

If Thunderbird is configured to use SSL/TLS for a given account or
outgoing mail server then the connections are always encrypted. Always.
STARTTLS is opportunistic so connections might or might not be encrypted.

-- 
Rich P.