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Asked: 2020-11-25 06:17:35 +0800 CST

Postfix can't send mails to gmail - sender non-delivery notification

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Having some troubles sending mails to gmail with Postfix. Below is my log:

Nov 24 15:07:02 ubuntu-4gb-fsn1-1 postfix/pickup[101539]: 4C99C4225A: uid=33 from=<www-data>
Nov 24 15:07:02 ubuntu-4gb-fsn1-1 postfix/cleanup[101916]: 4C99C4225A: message-id=<20201124140702.4C99C4225A@ubuntu-4gb-fsn1-1>
Nov 24 15:07:02 ubuntu-4gb-fsn1-1 postfix/qmgr[65515]: 4C99C4225A: from=<[email protected]>, size=329, nrcpt=1 (queue active)
Nov 24 15:07:03 ubuntu-4gb-fsn1-1 postfix/smtp[101918]: 4C99C4225A: to=<[email protected]>, relay=mx-eu.mail.am0.yahoodns.net[188.125.72.74]:25, d
elay=0.91, delays=0.02/0.01/0.34/0.52, dsn=2.0.0, status=sent (250 ok dirdel)
Nov 24 15:07:03 ubuntu-4gb-fsn1-1 postfix/qmgr[65515]: 4C99C4225A: removed
Nov 24 15:07:58 ubuntu-4gb-fsn1-1 postfix/pickup[101539]: 9552D4225A: uid=33 from=<www-data>
Nov 24 15:07:58 ubuntu-4gb-fsn1-1 postfix/cleanup[101916]: 9552D4225A: message-id=<20201124140758.9552D4225A@ubuntu-4gb-fsn1-1>
Nov 24 15:07:58 ubuntu-4gb-fsn1-1 postfix/qmgr[65515]: 9552D4225A: from=<[email protected]>, size=332, nrcpt=1 (queue active)
Nov 24 15:07:59 ubuntu-4gb-fsn1-1 postfix/smtp[101918]: 9552D4225A: to=<[email protected]>, relay=gmail-smtp-in.l.google.com[2a00:1450:400c:c0c::1b]:25, delay=0.76, delays=0.01/0/0.13/0.61, dsn=5.7.1, status=bounced (host gmail-smtp-in.l.google.com[2a00:1450:400c:c0c::1b] said: 550-5.7.1 [2a01:4f8:c010:3127::1] Our system has detected that this message does 550-5.7.1 not meet IPv6 sending guidelines regarding PTR records and 550-5.7.1 authentication. Please review 550-5.7.1  https://support.google.com/mail/?p=IPv6AuthError for more information 550 5.7.1 . n11si2614598wma.157 - gsmtp (in reply to end of DATA command))
Nov 24 15:07:59 ubuntu-4gb-fsn1-1 postfix/cleanup[101916]: 5B1304225D: message-id=<20201124140759.5B1304225D@ubuntu-4gb-fsn1-1>
Nov 24 15:07:59 ubuntu-4gb-fsn1-1 postfix/bounce[101930]: 9552D4225A: sender non-delivery notification: 5B1304225D
Nov 24 15:07:59 ubuntu-4gb-fsn1-1 postfix/qmgr[65515]: 5B1304225D: from=<>, size=3011, nrcpt=1 (queue active)
Nov 24 15:07:59 ubuntu-4gb-fsn1-1 postfix/qmgr[65515]: 9552D4225A: removed
Nov 24 15:07:59 ubuntu-4gb-fsn1-1 postfix/local[101931]: 5B1304225D: to=<[email protected]>, relay=local, delay=0.01, delays=0/0.01/0/0, dsn=2.0.0, status=sent (delivered to mailbox)
Nov 24 15:07:59 ubuntu-4gb-fsn1-1 postfix/qmgr[65515]: 5B1304225D: removed
Nov 24 15:20:21 ubuntu-4gb-fsn1-1 postfix/pickup[101539]: 714A94225D: uid=33 from=<www-data>
Nov 24 15:20:21 ubuntu-4gb-fsn1-1 postfix/cleanup[102121]: 714A94225D: message-id=<20201124142021.714A94225D@ubuntu-4gb-fsn1-1>
Nov 24 15:20:21 ubuntu-4gb-fsn1-1 postfix/qmgr[65515]: 714A94225D: from=<[email protected]>, size=328, nrcpt=1 (queue active)
Nov 24 15:20:21 ubuntu-4gb-fsn1-1 postfix/smtp[102123]: 714A94225D: host mx1.pub.mailpod9-cph3.one.com[185.164.14.118] said: 450 4.7.1 138.119.249.183 temporary greylisted by CYREN IP reputation (in reply to MAIL FROM command)
Nov 24 15:20:21 ubuntu-4gb-fsn1-1 postfix/smtp[102123]: 714A94225D: lost connection with mx1.pub.mailpod9-cph3.one.com[185.164.14.118] while sending RCPT TO
Nov 24 15:20:22 ubuntu-4gb-fsn1-1 postfix/smtp[102123]: 714A94225D: to=<[email protected]>, relay=mx3.pub.mailpod9-cph3.one.com[185.164.14.120]:25, delay=0.92, delays=0.02/0.02/0.82/0.07, dsn=4.7.1, status=deferred (host mx3.pub.mailpod9-cph3.one.com[185.164.14.120] said: 450 4.7.1 138.119.249.183 temporary greylisted by CYREN IP reputation (in reply to MAIL FROM command))
Nov 24 15:27:09 ubuntu-4gb-fsn1-1 postfix/qmgr[65515]: 714A94225D: from=<[email protected]>, size=328, nrcpt=1 (queue active)
Nov 24 15:27:10 ubuntu-4gb-fsn1-1 postfix/smtp[102169]: 714A94225D: host mx3.pub.mailpod9-cph3.one.com[185.164.14.120] said: 450 4.7.1 138.119.249.183 temporary greylisted by CYREN IP reputation (in reply to MAIL FROM command)

Nov 24 15:27:10 ubuntu-4gb-fsn1-1 postfix/smtp[102169]: 714A94225D: lost connection with mx3.pub.mailpod9-cph3.one.com[185.164.14.120] while sending RCPT TO
Nov 24 15:27:10 ubuntu-4gb-fsn1-1 postfix/smtp[102169]: 714A94225D: to=<[email protected]>, relay=mx2.pub.mailpod9-cph3.one.com[185.164.14.119]:25, delay=409, delays=408/0.02/0.57/0.05, dsn=4.7.1, status=deferred (host mx2.pub.mailpod9-cph3.one.com[185.164.14.119] said: 450 4.7.1 138.119.249.183 temporary greylisted by CYREN IP reputation (in reply to MAIL FROM command))
(END)

You can see that no issue with yahoo. But you get a sender non-delivery notification for gmail.

Any ideas why?

My Postfix config:

smtpd_banner = $myhostname ESMTP $mail_name (Ubuntu)
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_tls_security_level=may

smtp_tls_CApath=/etc/ssl/certs
smtp_tls_security_level=may
smtp_tls_session_cache_database = btree:${data_directory}/smtp_scache

smtpd_relay_restrictions = permit_mynetworks permit_sasl_authenticated defer_unauth_destination
myhostname = ubuntu-4gb-fsn1-1
alias_maps = hash:/etc/aliases
alias_database = hash:/etc/aliases
myorigin = /etc/mailname
mydestination = my-domain.com, $myhostname, ubuntu-4gb-fsn1-1, localhost.localdomain, localhost
relayhost =
mynetworks = 127.0.0.0/8 [::ffff:127.0.0.0]/104 [::1]/128
mailbox_size_limit = 0
recipient_delimiter = +
inet_interfaces = loopback-only
inet_protocols = all
email gmail postfix yahoo

1 Answers

  1. You have the reason fully explained in the bounce message from Google:

    550-5.7.1 [2a01:4f8:c010:3127::1] Our system has detected that this message does 550-5.7.1 not meet IPv6 sending guidelines regarding PTR records and 550-5.7.1 authentication. Please review 550-5.7.1 https://support.google.com/mail/?p=IPv6AuthError for more information

    So you have to read information at the specified URL and configure your mailserver as specified there.

    Also note that some other receiving host is saying to you: 450 4.7.1 138.119.249.183 temporary greylisted by CYREN IP reputation. Your server's IP is indicated as a "bad reputation" at some service called CYREN (sorry, I don't know what it is - you have to look up for yourself). You may need to resolve the issue as well to get your mail delivered to Google, as Google is very sensitive to "bad reputation" IPs.

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