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I have configured exim4 and am trying to send out emails using port 587 and the email is being sent but on the mail server it show connecting at port 25. I am using:

echo "Subject:Hello All" | sendmail -v  -port 587 [email protected]


T: remote_smtp for [email protected]
Connecting to gmail-smtp-in.l.google.com [2607:f8b0:4004:c08::1a]:25 ... LOG: MAIN

(Not pasting the entire output of the log here)

+++++++++++++++++++++ I wanted to check why the connection goes to port 25 as shown below---- """Connecting to gmail-smtp-in.l.google.com [2607:f8b0:4004:c08::1a]:25 ... LOG: MAIN""""

I want all my email to connect on port 587 as I have requested for port 587. I have tried most of the settings shown online in the exim4 config file. But still it connects on 25. Links that I followed but no luck : https://www.fyzix.net/index.php?title=Installing_and_Configuring_Exim4_for_Gmail_SMTP_Relay and https://logs.paulooi.com/enable-smtp-port-587-on-exim.php

Also, any mail server I use... it connects to port 25..

Could anyone help me here ?

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2 Answers 2

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The easiest way I found to get this working is to add port = 587 to the remote_smtp_smarthost: section in /etc/exim4/conf.d/transport/30_exim4-config_remote_smtp_smarthost

This only works if you're using the split-files config approach, chosen via e.g. dpkg-reconfigure exim4-config. Otherwise you have to edit /etc/exim4/exim4.conf.template (same section).

Then run update-exim4.conf to generate the final config file (/var/lib/exim4/config.autogenerated).

Then restart the exim daemon, e.g. systemctl restart exim4.

(There are probably other/more correct ways to configure this by messing with the driver directive or TLS settings, but for some reason it doesn't work out-of-the-box on Debian, even after specifying port 587 in the SMTP url via dpkg-reconfigure exim4-config. The docs are enormous.)

See also https://www.fyzix.net/index.php?title=Installing_and_Configuring_Exim4_for_Gmail_SMTP_Relay

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It seems your Exim server is accepting email at port 587, but when it comes to delivering mail, it is not properly configured to establish a TLS/SSL connection to the destination server -- that's why it is connecting to the non-SSL port 25--. You need to get acquainted with Exim SSL/TLS configuration, install a digital certificate and configure Exim to require SSL/TLS connections when delivering messages.

Besides, some remote SMTP servers may want to establish secure connections through different ports, like 465, 587 and --yes-- 25. This depends on the local set up of the remote server.

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