Configuring Postfix with Yandex.ru relay in Ubuntu 16.04

Today I read that Postfix can be better than sendmail and found a great Russian article on how to configure Postfix to work with Yandex.ru relay (Yandex.ru is some kind of Russian Google). The only notice I would give is that in a Docker container I need also install rsyslog, otherwise /var/log/mail.log file is not created:

apt install rsyslog

After doing all the steps described in this Russian manual I was able to send email to Yandex.ru and GMail accounts, but GMail landed all the emails to its spam folder. My first idea was that it is because I did not configure ‘from address’ correctly, so I had the following in /var/log/mail.log, and also there was a message ‘Cannot assign requested address‘:

Oct 27 11:36:19 0675c97b78aa postfix/pickup[1210]: 8C7ECE5B72: uid=0 from=<root>
Oct 27 11:36:19 0675c97b78aa postfix/cleanup[10786]: 8C7ECE5B72: message-id=<20171027113619.8C7ECE5B72@0675c97b78aa.localdomain>
Oct 27 11:36:19 0675c97b78aa postfix/qmgr[1211]: 8C7ECE5B72: from=<root@0675c97b78aa.localdomain>, size=405, nrcpt=2 (queue active)
Oct 27 11:36:19 0675c97b78aa postfix/smtp[10788]: connect to gmail-smtp-in.l.google.com[2a00:1450:400c:c09::1b]:25: Cannot assign requested address
...

And email header in GMail inbox contained ‘localdomain address’:

Received-SPF: neutral (google.com: 139.162.243.103 is neither permitted nor denied by best guess record for domain of root@0675c97b78aa.localdomain) client-ip=139.162.243.103;
Subject: test mail to Some Address!
To: Me <XXX@gmail.com>
From: Vasya <XXX@yandex.ru>
Message-Id: <20171027123619.5F04FE5B72@0675c97b78aa.localdomain>
Date: Fri, 27 Oct 2017 12:36:19 +0000 (UTC)

first line of my message

In Yandex.ru inbox:

Received: from mxfront12g.mail.yandex.net ([127.0.0.1])
	by mxfront12g.mail.yandex.net with LMTP id g8Rq5bAq;
	Fri, 27 Oct 2017 14:32:30 +0300
Received: from li1528-103.members.linode.com (li1528-103.members.linode.com [139.162.243.103])
	by mxfront12g.mail.yandex.net (nwsmtp/Yandex) with ESMTP id IIHHej4nOp-WTZOkxWK;
	Fri, 27 Oct 2017 14:32:29 +0300
Return-Path: root@0675c97b78aa.localdomain
X-Yandex-Front: mxfront12g.mail.yandex.net
X-Yandex-TimeMark: 1509103949
X-Yandex-Spam: 1
Received: by 0675c97b78aa.localdomain (Postfix, from userid 0)
	id D354BE5B72; Fri, 27 Oct 2017 11:32:28 +0000 (UTC)
To: XXX@yandex.ru
Subject: My subject 1
X-PHP-Originating-Script: 1000:send.php
From: XXX@gmail.com
CC: XXX@yandex.ru
Message-Id: <20171027113228.D354BE5B72@0675c97b78aa.localdomain>
Date: Fri, 27 Oct 2017 11:32:28 +0000 (UTC)
X-Yandex-Forward: 83938fd9893ad788cf792ddfa68a0e0a
X-Yandex-Forward: a8c50329ae5e4eaa440a48a9e2df76be

First line of text
Second line of text

I tried the following links, but with no success yet:

Google spam filter is still filtering the messages out.

To remove sendmail I did this:

apt-get remove --auto-remove sendmail*
apt-get purge --auto-remove sendmail*

One year later (on October 18, 2018) I realized that the information provided above is not quite correct, because postfix sends mail via yandex.ru only if sendmail is run with -f option like this:

/usr/sbin/sendmail -t -f username1@yandex.ru -i -v < body.txt

where body.txt contains

Subject: test mail to My Address!
From: Me <username2@gmail.com>
To: Vasya <username1@yandex.ru>
Firt line of my message 1

This makes postfix really use yandex.ru but it connects to port 25:

Oct 18 09:18:36 localhost postfix/pickup[12794]: 8634C13FAC1: uid=1000 from=<username1@yandex.ru>
Oct 18 09:18:36 localhost postfix/cleanup[20334]: 8634C13FAC1: message-id=<20181018091836.8634C13FAC1@localhost.localdomain>
Oct 18 09:18:36 localhost postfix/qmgr[12795]: 8634C13FAC1: from=<username1@yandex.ru>, size=353, nrcpt=1 (queue active)
Oct 18 09:18:36 localhost postfix/smtp[20336]: 8634C13FAC1: to=<username1@yandex.ru>, relay=smtp.yandex.ru[77.88.21.38]:25, delay=0.41, delays=0.01/0.01/0.34/0.05, dsn=5.5.4, status=bounced (host smtp.yandex.ru[77.88.21.38] said: 503 5.5.4 Error: send AUTH command first. (in reply to MAIL FROM command))
Oct 18 09:18:37 localhost postfix/cleanup[20334]: 1A6BA140184: message-id=<20181018091837.1A6BA140184@localhost.localdomain>
Oct 18 09:18:37 localhost postfix/qmgr[12795]: 1A6BA140184: from=<>, size=2424, nrcpt=1 (queue active)
Oct 18 09:18:37 localhost postfix/bounce[20337]: 8634C13FAC1: sender non-delivery notification: 1A6BA140184
Oct 18 09:18:37 localhost postfix/cleanup[20334]: 1B56413F811: message-id=<20181018091837.1B56413F811@localhost.localdomain>
Oct 18 09:18:37 localhost postfix/qmgr[12795]: 1B56413F811: from=<>, size=2195, nrcpt=1 (queue active)
Oct 18 09:18:37 localhost postfix/bounce[20338]: 8634C13FAC1: sender delivery status notification: 1B56413F811
Oct 18 09:18:37 localhost postfix/qmgr[12795]: 8634C13FAC1: removed
Oct 18 09:18:38 localhost postfix/smtp[20336]: 1A6BA140184: to=<username1@yandex.ru>, relay=mx.yandex.ru[2a02:6b8::89]:25, delay=1.2, delays=0/0/0.24/0.95, dsn=2.0.0, status=sent (250 2.0.0 Ok: queued on mxfront2j.mail.yandex.net as 1539854318-7qirx3cq9t-IbFaJ8Db)
Oct 18 09:18:38 localhost postfix/qmgr[12795]: 1A6BA140184: removed
Oct 18 09:18:38 localhost postfix/smtp[20339]: 1B56413F811: to=<username1@yandex.ru>, relay=mx.yandex.ru[93.158.134.89]:25, delay=1.3, delays=0/0.01/0.3/1, dsn=2.0.0, status=sent (250 2.0.0 Ok: queued on mxfront8j.mail.yandex.net as 1539854318-SBx7LC1MXf-IbiG2Owr)
Oct 18 09:18:38 localhost postfix/qmgr[12795]: 1B56413F811: removed

To make it connect to port 465 I installed stunnel:

sudo apt install stunnel
sudo nano /etc/stunnel/yandex.conf

[smtp]
client = yes
accept = 127.0.0.1:25025
connect = smtp.yandex.ru:465

sudo nano /etc/default/stunnel4

# Change to one to enable stunnel automatic startup
ENABLED=1

sudo service stunnel4 restart
telnet localhost 25025

Trying 127.0.0.1...
Connected to 127.0.0.1.
Escape character is '^]'.
220 smtp4j.mail.yandex.net ESMTP (Want to use Yandex.Mail for your domain? Visit http://pdd.yandex.ru)

sudo nano /etc/postfix/main.cf

relayhost = localhost:25025
smtp_sasl_auth_enable = yes
smtp_sasl_password_maps = hash:/etc/postfix/private/sasl_passwd
smtp_sasl_security_options = noanonymous
smtp_sasl_type = cyrus
smtp_sasl_mechanism_filter = login
smtp_sender_dependent_authentication = yes
sender_dependent_relayhost_maps = hash:/etc/postfix/private/sender_relay
sender_canonical_maps = hash:/etc/postfix/private/canonical
compatibility_level=2

sudo service postfix restart

and something strange started to happen:

Oct 18 09:57:14 localhost postfix/pickup[22171]: 2207213FB7D: uid=1000 from=<username1@yandex.ru>
Oct 18 09:57:14 localhost postfix/cleanup[22218]: 2207213FB7D: message-id=<20181018095714.2207213FB7D@localhost.localdomain>
Oct 18 09:57:14 localhost postfix/qmgr[22172]: 2207213FB7D: from=<username1@yandex.ru>, size=353, nrcpt=1 (queue active)
Oct 18 09:57:14 localhost postfix/smtp[22220]: 2207213FB7D: to=<username1@yandex.ru>, relay=smtp.yandex.ru[213.180.193.38]:25, delay=0.42, delays=0.01/0.01/0.35/0.05, dsn=5.5.4, status=bounced (host smtp.yandex.ru[213.180.193.38] said: 503 5.5.4 Error: send AUTH command first. (in reply to MAIL FROM command))
Oct 18 09:57:14 localhost postfix/cleanup[22218]: AD7C01412AB: message-id=<20181018095714.AD7C01412AB@localhost.localdomain>
Oct 18 09:57:14 localhost postfix/qmgr[22172]: AD7C01412AB: from=<>, size=2427, nrcpt=1 (queue active)
Oct 18 09:57:14 localhost postfix/bounce[22221]: 2207213FB7D: sender non-delivery notification: AD7C01412AB
Oct 18 09:57:14 localhost postfix/cleanup[22218]: AE53F13FB7C: message-id=<20181018095714.AE53F13FB7C@localhost.localdomain>
Oct 18 09:57:14 localhost postfix/qmgr[22172]: AE53F13FB7C: from=<>, size=2201, nrcpt=1 (queue active)
Oct 18 09:57:14 localhost postfix/bounce[22222]: 2207213FB7D: sender delivery status notification: AE53F13FB7C
Oct 18 09:57:14 localhost postfix/qmgr[22172]: 2207213FB7D: removed
Oct 18 09:57:15 localhost postfix/smtp[22224]: AE53F13FB7C: to=<username1@yandex.ru>, relay=localhost[127.0.0.1]:25025, delay=0.39, delays=0/0.01/0.33/0.06, dsn=5.5.4, status=bounced (host localhost[127.0.0.1] said: 503 5.5.4 Error: send AUTH command first. (in reply to MAIL FROM command))
Oct 18 09:57:15 localhost postfix/smtp[22220]: AD7C01412AB: to=<username1@yandex.ru>, relay=localhost[127.0.0.1]:25025, delay=0.43, delays=0/0/0.38/0.05, dsn=5.5.4, status=bounced (host localhost[127.0.0.1] said: 503 5.5.4 Error: send AUTH command first. (in reply to MAIL FROM command))
Oct 18 09:57:15 localhost postfix/qmgr[22172]: AE53F13FB7C: removed
Oct 18 09:57:15 localhost postfix/qmgr[22172]: AD7C01412AB: removed

Installing sasl2 does not have an effect:

sudo apt install sasl2-bin
sudo service postfix restart

So I tried another alternative without stunnel:

First I got the certificate from Yandex with the following command:

openssl s_client -starttls smtp -crlf -connect smtp.yandex.ru:25

and saved it as /etc/postfix/private/yandex.crt.

In /etc/postfix/private/sasl_passwd:

[smtp.yandex.com]:587   username1@yandex.ru:**********

postmap sasl_passwd

In /etc/postfix/main.cf:

relayhost = [smtp.yandex.com]:587
smtp_use_tls = yes
smtp_sasl_auth_enable = yes
smtp_sasl_password_maps = hash:/etc/postfix/private/sasl_passwd
smtp_sasl_security_options =
smtp_tls_CAfile = /etc/postfix/private/yandex.crt
compatibility_level=2

and it started to work somehow.

1 Response to Configuring Postfix with Yandex.ru relay in Ubuntu 16.04

dmitriano says:

June 12, 2020 at 2:44 pm

When I change my mail password I update `/etc/postfix/private/sasl_passwd` and generate `sasl_passwd.db` with `postmap sasl_passwd` command. If the password is incorrect I can see the following messages with `tail -n 100 mail.log` command:
…
Jun 12 17:31:38 localhost postfix/smtp[583]: 420816796: SASL authentication failed; server smtp.yandex.com[77.88.21.158] said: 535 5.7.8 Error: authentication failed: Invalid user or password!
…

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