The tracing didn't reveal any clues.  No mention of TLS at all.

smtp: 0x8027726c0: connected to listener 0x802653000 [hostname=
mail.mydomain.net, port=25, tag=]
smtp: 0x8027726c0: STATE_NEW -> STATE_CONNECTED
smtp: 0x8027726c0: >>> 220 mail.mydomain.net ESMTP OpenSMTPD
smtp: 0x8027726c0: <<< HELO jmann-mbp
smtp: 0x8027726c0: STATE_CONNECTED -> STATE_HELO
smtp: 0x8027726c0: >>> 250 mail.mydomain.net Hello jmann-mbp
[IPv6:0000:000:0000:000:0000:0000:0000:000], pleased to meet you
smtp: 0x8027726c0: <<< MAIL FROM:<jmann@jmann-mbp>
smtp: 0x8027726c0: >>> 250 2.0.0: Ok
smtp: 0x8027726c0: <<< RCPT TO:<[email protected]>
expand: 0x8026d4018: expand_insert() called for address:[email protected]
[parent=0x0]
expand: 0x8026d4018: inserted node 0x802616f00
expand: lka_expand: address: [email protected] [depth=0]
lookup: check "ipv6:0000:000:0000:000:0000:0000:0000:000" as NETADDR in
table static:<anyhost> -> found
lookup: check "mydomain.net" as DOMAIN in table static:vdomains -> found
rule matched: accept from <anyhost> for  domain vdomains virtual vusers
deliver to maildir "~/Maildir"
expand: 0x802688750: expand_insert() called for username:jason[parent=0x0]
expand: 0x802688750: inserted node 0x802618300
lookup: lookup "[email protected]" as ALIAS in table static:vusers ->
"jason"
expand: 0x8026d4018: expand_insert() called for
username:jason[parent=0x802616f00, mapping=vusers, userbase=<getpwnam>]
expand: 0x8026d4018: inserted node 0x802617400
expand: 0x802688750: clearing expand tree
expand: 0x802688750: freeing expand tree
expand: lka_expand: username: jason [depth=1]
lookup: lookup "jason" as ALIAS in table static:vusers -> 0
lookup: lookup "jason" as USERINFO in table getpwnam:<getpwnam> ->
"jason:1000:1000:/home/jason"
expand: no .forward for user jason, just deliver
lookup: lookup "jason" as USERINFO in table getpwnam:<getpwnam> ->
"jason:1000:1000:/home/jason"
expand: 0x8026d4018: clearing expand tree
smtp: 0x8027726c0: >>> 250 2.1.5 Destination address valid: Recipient ok
smtp: 0x8027726c0: <<< DATA
smtp: 0x8027726c0: STATE_HELO -> STATE_BODY
smtp: 0x8027726c0: >>> 354 Enter mail, end with "." on a line by itself
<<< [MSG] From: Jason Mann <jmann@jmann-mbp>
<<< [MSG] To: Jason Mann <[email protected]>
<<< [MSG] Subject: Test 4
<<< [MSG]
<<< [MSG] This is a test.
<<< [EOM]
smtp: 0x8027726c0: >>> 250 2.0.0: 0c579ba5 Message accepted for delivery
smtp: 0x8027726c0: STATE_BODY -> STATE_HELO
lookup: lookup "jason" as USERINFO in table getpwnam:<getpwnam> ->
"jason:1000:1000:/home/jason"
smtp: 0x8027726c0: <<< QUIT
smtp: 0x8027726c0: >>> 221 2.0.0: Bye
smtp: 0x8027726c0: STATE_HELO -> STATE_QUIT

Kind regards,

Jason

On 28 January 2017 at 15:59, Marcus MERIGHI <[email protected]> wrote:

> [email protected] (Jason Mann), 2017.01.27 (Fri) 15:41 (CET):
> > Hello list.
> >
> > I'm trying to configure OpenSMTPD 5.9.2 on a FreeBSD server but I'm
> seeing
> > anomalous behaviour with one of my listen directives.
> >
> > The directive in question is:
> >
> >   listen on egress tls-require hostname mail.mydomain.net
> >
> > My only other listen directive is usual localhost one.
> >
> > The smtpd.conf man page states: "tls-require may be used to force clients
> > to establish a secure connection before being allowed to start an SMTP
> > transaction".
> >
> > I ran a telnet test against the server to see how the forcing of TLS
> takes
> > place, but it didn't happen.  I was able to manually submit a message to
> > OpenSMTPD without TLS as follows:
>
> $ for i in smtp mta expand lookup rules; do smtpctl trace $i; done
> (do your test and watch your logfiles to see what goes why where.)
> $ for i in smtp mta expand lookup rules; do smtpctl untrace $i; done
>
> Be quick, lots of output to your log file.
>
> Marcus
>
> > $ telnet a.mx.mydomain.net 25
> > Trying xxxx:xxx:xx:xxx::x:xxxx...
> > Connected to a.mx.mydomain.net.
> > Escape character is '^]'.
> > 220 mail.mydomain.net ESMTP OpenSMTPD
> > HELO jmann-mbp
> > 250 mail.mydomain.net Hello jmann-mbp
> > [IPv6:xxxx:xxxx:xxxx:xxxx:xxxx:xxxx:xxxx:xxxx],
> > pleased to meet you
> > MAIL FROM:<jmann@jmann-mbp>
> > 250 2.0.0: Ok
> > RCPT TO:<[email protected]>
> > 250 2.1.5 Destination address valid: Recipient ok
> > DATA
> > 354 Enter mail, end with "." on a line by itself
> > From: Jason Mann <jmann@jmann-mbp>
> > To: Jason Mann <[email protected]>
> > Subject: Test 4
> >
> > This is a test.
> > .
> > 250 2.0.0: f20f3998 Message accepted for delivery
> > QUIT
> > 221 2.0.0: Bye
> >
> > What may be wrong here?
> >
> > Kind regards,
> >
> > Jason
> >
> >
> > !DSPAM:588b5c5b241071631238794!
>

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