On 11/22/18 1:11 AM, Gilles Chehade wrote:
On Tue, Nov 13, 2018 at 09:59:29PM -0600, Edgar Pettijohn III wrote:
I have the following line on my laptops smtpd.conf:

action "relay" relay host "smtp+tls//label@domain:587" auth <secrets> tls
no-verify

I had to add the no-verify for some reason with the upgrade to 6.4. I was
trying to figure out why tls was failing, so I started testing with openssl
s_client and it wasn't being very useful. I looked at the logs on the server
and this is what it shows:

Nov 13 21:47:40 mail smtpd[37181]: bee1391f24a23978 smtp failed-command
address=50.55.65.87 host=50.55.65.87 command="pipelining" result="500 5.5.1
Invalid command: Command unrecognized"
Nov 13 21:47:50 mail smtpd[37181]: bee1391f24a23978 smtp disconnected
address=50.55.65.87 host=50.55.65.87 reason=disconnect

I'm not sure if this is an smtpd bug or an s_client bug or neither.

without the command line you used, i can only take guesses.

the sample config line you show hints that the host you're connecting to
supports TLS through the STARTTLS extension so you have to establish the
connection using plain SMTP then upgrade to TLS.

the pipelining error hints that the SMTP protocol was not respected when
your client connected, which makes me assume you didn't connect in plain
and upgrade to TLS but you connected and issued a TLS negotiation out of
the blue (aka. SMTPS).

so I guess you used something like:

   $ openssl s_client -host 50.55.65.87 -port 587

instead of:

   $ openssl s_client -host 50.55.65.87 -port 587 -starttls smtp



Yep I forgot -starttls smtp :)

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