On 5/14/2025 12:01 PM, Bill Cole via mailop wrote:
On 2025-05-14 at 10:50:52 UTC-0400 (Wed, 14 May 2025 10:50:52 -0400)
Scott Q. via mailop <qm...@top-consulting.net>
is rumored to have said:
openssl s_client -connect smtp.secureserver.net:25 -starttls smtp
CONNECTED(00000004)
Didn't find STARTTLS in server response, trying anyway...
That says something significant. Your mail server wouldn't happen to be
living behind a Cisco firewall, would it?
If s_client says that, then it has successfully connected, sent a EHLO
command, and got something in response.
If it isn't seeing STARTTLS then either STARTTLS wasn't offered *OR*
some middlebox interfering with SMTP removed it. In my quick testing,
the machines answering behind smtp.secureserver.net all offer STARTTLS.
This is not Cisco specific. Several flavors of firewalls force
clear-text for inspection purposes these days. But I think you are onto
something there.
With Gratitude,
Dave Brockman
Senior Network Engineer
Gig City Cloud, LLC
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