On 2019-11-27 10:04 a.m., Heiko Schlittermann via Exim-users wrote:
Hi,

Gary Dale via Exim-users <exim-users@exim.org> (Mi 27 Nov 2019 10:21:18 CST):
mail from: sendmail@rossland.dental
250 OK
rcpt to: sendmail@rossland.dental
250 Accepted
data
354 Enter message, ending with "." on a line by itself
from: sendmail@rossland.dental
to: g...@extremeground.com, garyd...@rogers.com
Date: 26 Nov 2019 20:59:00 -0500
subject: test message from s_client with 2 recipients
another test message - with a date possibly.
.
250 OK id=1iZmbP-005vB9-E0
DONE

The mail doesn't get to either "to:" address but does show up in the "rcpt
to:" inbox.
Yes, it is exactly as mail is supposed to work. The SMTP RCPT TO is the
address, the mail system will deliver the message to (call it the
"envelope"). The To: line is part of the message, a mail system should
not care about the message (to a limited extend).

 From the above, I gather that I have the correct names, ports and
credentials. However I'm not able to send mail. It just sits in my server's
mailq.
I do not understand. Above you stated, the mail shows up in the rcpt
to's inbox (the envelope recipient's inbox). No you're telling us, that
it sits in the queue. I'm lost.

Different servers. When I use s_client to connect to the remote server, I get mail. When I send it from my local exim4 server, I don't.



Here's my update-exim4.conf.conf file.

dc_eximconfig_configtype='smarthost'
dc_other_hostnames='molar.rossland.dental'
dc_local_interfaces='127.0.0.1 ; ::1'
dc_readhost=''
dc_relay_domains=''
dc_minimaldns='false'
dc_relay_nets=''
dc_smarthost='mail.rossland.dental::465'
CFILEMODE='644'
dc_use_split_config='false'
dc_hide_mailname='false'
dc_mailname_in_oh='true'
dc_localdelivery='mail_spool'
I'm not sure, if Exim is meanwhile able to use SMTPS (TLS-on-connect) as
a client. As a server, it does, but as a client?

Ah, the spec tells me, it does. There is a SMTP transport option
"protocol", it may be set to "smtps".

So, you'll need to fiddle with your configuration (or with the Debian
provided config files) to use the "protocol" option. Or - try if
molar.rossland.dental allow submission on port 587.

I had thought that was required only if the "Connection security" (to use Thunderbird's terminology was STARTTLS. However I followed the instructions at https://dantalion.nl/en/configure-exim4-smtp-relay-to-use-tls-on-connect/ to set up smtps but that failed also. The test message sent by swaks (in the testing section of the howto) again simply sits in the mailq.

I followed the instructions exactly, which apart from the config settings, also requires setting the .template file to include a couple of lines as follows:

remote_smtp_smarthost:
  debug_print = "T: remote_smtp_smarthost for $local_part@$domain"
  driver = smtp
*  hosts_require_tls = mail.rossland.dental**
**  protocol = smtps**
*  multi_domain

Still no joy in Mudville.

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