On Wed 22 Mar 2023 at 13:52:00 (-0700), pe...@easthope.ca wrote: > > After configuring exim for a new smarthost, message sending fails.
What are the contents of /etc/exim4/update-exim4.conf.conf, the configuration file? > This might help to identify the problem. > > root@dalton:/home/root# exim -bh 142.103.1m.1n I've not used this facility before, but it seems to work: > **** SMTP testing session as if from host 142.103.1m.1n > **** but without any ident (RFC 1413) callback. > **** This is not for real! > > > > > host in hosts_connection_nolog? no (option unset) > > > > host in host_lookup? yes (matched "*") > > > > looking up host name for 142.103.1m.1n > > > > IP address lookup yielded "dalton.invalid" > > > > checking addresses for dalton.invalid > > > > 142.103.1m.1n OK > > > > host in host_reject_connection? no (option unset) > > > > host in sender_unqualified_hosts? no (option unset) > > > > host in recipient_unqualified_hosts? no (option unset) > > > > host in helo_verify_hosts? no (option unset) > > > > host in helo_try_verify_hosts? no (option unset) > > > > host in helo_accept_junk_hosts? no (option unset) > > > > host in pipelining_connect_advertise_hosts? yes (matched "*") > 220 dalton.invalid ESMTP Exim 4.94.2 Wed, 22 Mar 2023 13:02:25 -0700 > > LOG: SMTP syntax error in "" H=dalton.invalid [142.103.1m.1n] ↑↑ So there's a syntax command in the empty string, which would be a reasonable reaction from exim. > unrecognized command > 500 unrecognized command > LOG: SMTP command timeout on connection from dalton.invalid > [142.103.1m.1n] > 421 dalton.invalid: SMTP command timeout - closing connection > root@dalton:/home/root# I assumed you just stared at the screen until this timeout appeared. From man exim: -bh <IP address> This option runs a fake SMTP session as if from the given IP address, using the standard input and output. The IP address may include a port number at the end, after a full stop. For example: exim4 -bh 10.9.8.7.1234 You've now got to type something. It will then talk back to you. Try typing (ignore my indentation): ehlo dalton.invalid ← that's not a typo mail from: pe...@easthope.ca rcpt to: pe...@easthope.ca data from: pe...@easthope.ca to: pe...@easthope.ca subject: hand written test 01 ← that's a blank line Hand written test 01 . ← that's nothing but a fullstop Return quit How far you get in this conversation depends what it says back. You want to see several 250s, and a 354 after you type DATA. > A test message produces this in /var/log/exim4/mainlog > > 2023-03-22 13:39:10 1pf5Ek-0000gQ-Dk <= pe...@easthope.ca > H=localhost.localdomain (dalton) [127.0.0.1] P=smtp S=586 Yes, that does look somewhat lacking. > 2023-03-22 13:39:10 1pf5Ek-0000gQ-Dk == pe...@easthope.ca R=smarthost > T=remote_smtp_smarthost defer (-53): retry time not reached for any host for > 'easthope.ca' Cheers, David.