Postfix via Gmail SMTP Error with no cause

Question

I'm trying to configure POSTFIX to send emails via smtp.gmail.com, without any success. Iv'e tried following these two tutorials:
https://www.endpoint.com/blog/2019/04/30/postfix-gmail-forwarder https://www.linode.com/docs/guides/configure-postfix-to-send-mail-using-gmail-and-google-apps-on-debian-or-ubuntu/
None of the tutorials worked, never mind what I do I get a bounced message in the log. Also It seems that when I'm sending an Email via sendmail my from address is overwritten with "root@observium-pi".

Also:I know that in principle it works because I have an OpenHAB smtp connector that sends successfully emails using the same SMTP.

Here is my main.cf:

# See /usr/share/postfix/main.cf.dist for a commented, more complete version


# Debian specific:  Specifying a file name will cause the first
# line of that file to be used as the name.  The Debian default
# is /etc/mailname.
#myorigin = /etc/mailname

smtpd_banner = $myhostname ESMTP $mail_name (Raspbian)
biff = no

# appending .domain is the MUA's job.
append_dot_mydomain = no

# Uncomment the next line to generate "delayed mail" warnings
#delay_warning_time = 4h

readme_directory = no

# See http://www.postfix.org/COMPATIBILITY_README.html -- default to 2 on
# fresh installs.
compatibility_level = 2



# TLS parameters
smtpd_tls_cert_file=/etc/ssl/certs/ssl-cert-snakeoil.pem
smtpd_tls_key_file=/etc/ssl/private/ssl-cert-snakeoil.key
smtpd_use_tls=yes
smtpd_tls_session_cache_database = btree:${data_directory}/smtpd_scache
smtp_tls_session_cache_database = btree:${data_directory}/smtp_scache

# See /usr/share/doc/postfix/TLS_README.gz in the postfix-doc package for
# information on enabling SSL in the smtp client.

#smtpd_relay_restrictions = permit_mynetworks permit_sasl_authenticated defer_unauth_destination
myhostname = observium-pi
alias_maps = hash:/etc/aliases
alias_database = hash:/etc/aliases
mydestination = $myhostname, observium-pi, localhost.localdomain, localhost
relayhost = [smtp.gmail.com]:465
mynetworks = 127.0.0.0/8 [::ffff:127.0.0.0]/104 [::1]/128
mailbox_size_limit = 0
recipient_delimiter = +
inet_interfaces = loopback-only
default_transport = error
relay_transport = error
inet_protocols = all
smtp_tls_wrappermode = yes
smtp_tls_security_level = verify
smtp_tls_mandatory_protocols = !SSLv2, !TLSv1, !TLSv1.1
tls_high_cipherlist = ECDHE-ECDSA-AES256-GCM-SHA384:ECDHE-RSA-AES256-GCM-SHA384:ECDHE-ECDSA-CHACHA20-POLY1305:ECDHE-RSA-CHACHA20-POLY1305:ECDHE-ECDSA-AES128-GCM-SHA256:ECDHE-RSA-AES128-GCM-SHA256:ECDHE-ECDSA-AES256-SHA384:ECDHE-RSA-AES256-SHA384:ECDHE-ECDSA-AES128-SHA256:ECDHE-RSA-AES128-SHA256
smtp_tls_mandatory_ciphers = high
smtp_tls_loglevel = 2

smtp_sasl_auth_enable = yes
smtp_sasl_mechanism_filter = plain
smtp_sasl_password_maps = hash:/etc/postfix/smtp_auth
smtp_sasl_security_options = noanonymous

header_checks = regexp:/etc/postfix/header_checks
You have new mail in /var/mail/root

Here is my smtp_auth (obfuscated), I'm using application specific password:

[smtp.gmail.com]:465 s******v@gmail.com:****************

and here is the log:

Jan 20 17:53:48 observium-pi postfix/pickup[13165]: 49AC73F2D5: uid=0 from=<root@observium-pi>
Jan 20 17:53:48 observium-pi postfix/cleanup[13725]: 49AC73F2D5: message-id=<20210120155348.49AC73F2D5@observium-pi>
Jan 20 17:53:48 observium-pi postfix/qmgr[13166]: 49AC73F2D5: from=<root@observium-pi>, size=354, nrcpt=1 (queue active)
Jan 20 17:53:48 observium-pi postfix/error[13727]: 49AC73F2D5: to=<s******v@gmail.com>, relay=none, delay=0.23, delays=0.13/0.04/0/0.06, dsn=5.0.0, status=bounced ([smtp.gmail.com]:465)
Jan 20 17:53:48 observium-pi postfix/cleanup[13725]: 728643F2D6: message-id=<20210120155348.728643F2D6@observium-pi>
Jan 20 17:53:48 observium-pi postfix/qmgr[13166]: 728643F2D6: from=<>, size=2169, nrcpt=1 (queue active)
Jan 20 17:53:48 observium-pi postfix/bounce[13728]: 49AC73F2D5: sender non-delivery notification: 728643F2D6
Jan 20 17:53:48 observium-pi postfix/qmgr[13166]: 49AC73F2D5: removed
Jan 20 17:53:49 observium-pi postfix/local[13729]: 728643F2D6: to=<root@observium-pi>, relay=local, delay=0.95, delays=0.02/0.05/0/0.88, dsn=2.0.0, status=sent (delivered to mailbox)
Jan 20 17:53:49 observium-pi postfix/qmgr[13166]: 728643F2D6: removed

Edit:

Contents of the bounce email:
From MAILER-DAEMON  Wed Jan 20 17:51:19 2021
Return-Path: <>
X-Original-To: root@observium-pi
Delivered-To: root@observium-pi
Received: by observium-pi (Postfix)
    id ECBA13F2D6; Wed, 20 Jan 2021 17:51:18 +0200 (IST)
Date: Wed, 20 Jan 2021 17:51:18 +0200 (IST)
From: MAILER-DAEMON@observium-pi (Mail Delivery System)
Subject: Undelivered Mail Returned to Sender
To: root@observium-pi
Auto-Submitted: auto-replied
MIME-Version: 1.0
Content-Type: multipart/report; report-type=delivery-status;
    boundary="2FE3A3F2D5.1611157878/observium-pi"
Content-Transfer-Encoding: 8bit
Message-Id: <20210120155118.ECBA13F2D6@observium-pi>
Status: O
X-UID: 17

This is a MIME-encapsulated message.

--2FE3A3F2D5.1611157878/observium-pi
Content-Description: Notification
Content-Type: text/plain; charset=utf-8
Content-Transfer-Encoding: 8bit

This is the mail system at host observium-pi.

I'm sorry to have to inform you that your message could not
be delivered to one or more recipients. It's attached below.

For further assistance, please send mail to postmaster.

If you do so, please include this problem report. You can
delete your own text from the attached returned message.

                   The mail system

<shaul@s******v.com>: [smtp.gmail.com]:465

--2FE3A3F2D5.1611157878/observium-pi
Content-Description: Delivery report
Content-Type: message/delivery-status

Reporting-MTA: dns; observium-pi
X-Postfix-Queue-ID: 2FE3A3F2D5
X-Postfix-Sender: rfc822; root@observium-pi
Arrival-Date: Wed, 20 Jan 2021 17:50:47 +0200 (IST)

Final-Recipient: rfc822; shaul@s******v.com
Original-Recipient: rfc822;shaul@s******v.com
Action: failed
Status: 5.0.0
Diagnostic-Code: X-Postfix; [smtp.gmail.com]:465

--2FE3A3F2D5.1611157878/observium-pi
Content-Description: Undelivered Message
Content-Type: message/rfc822
Content-Transfer-Encoding: 8bit

Return-Path: <root@observium-pi>
Received: by observium-pi (Postfix, from userid 0)
    id 2FE3A3F2D5; Wed, 20 Jan 2021 17:51:16 +0200 (IST)
from: s******v@gmail.com
subject: quick email
Message-Id: <20210120155117.2FE3A3F2D5@observium-pi>
Date: Wed, 20 Jan 2021 17:50:47 +0200 (IST)

sending a quick email

--2FE3A3F2D5.1611157878/observium-pi--

Is your password correct? Did you enable less secure apps in Gmail? — Michael Hampton, Jan 20 '21 at 23:13
I have two factor authentication enabled So I can't enable less secure apps. Instead I use app passwords (which works on my openhab installation). — Shaulliv, Jan 21 '21 at 08:30
OK, that should work fine. It doesn't make much sense for there to be no bounce message though. Are you sure you are actually connecting to Gmail and that your ISP has not interfered with your connection? — Michael Hampton, Jan 21 '21 at 12:36
Ok, I managed to "fix" it, it seems that for some reason TLS SMTP doesn't work on Debian buster (maybe there are some packages missing or on the wrong version). I reinstalled the system with Ubuntu server 20.04 and now it works fine. — Shaulliv, Jan 22 '21 at 14:13

Postfix via Gmail SMTP Error with no cause

0 Answers0