gmail doesn't accept any authentication SMPT email

Discussion:

(too old to reply)

Mohsen Pahlevanzadeh

2020-06-09 22:23:39 UTC

I send by my MTA to gmail account and I received the following message from gmail:
##########################################################
This is the mail system at host mail.pahlevanzadeh.net.

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

<***@gmail.com>: host gmail-smtp-in.l.google.com[172.217.222.27]
said: 550-5.7.26 This message does not have authentication information or
fails to 550-5.7.26 pass authentication checks. To best protect our users
from spam, the 550-5.7.26 message has been blocked. Please visit 550-5.7.26
https://support.google.com/mail/answer/81126#authentication for more 550
5.7.26 information. j14si2787252qvx.139 - gsmtp (in reply to end of DATA
command)

Reporting-MTA: dns; mail.pahlevanzadeh.net
X-Postfix-Queue-ID: 3FBAA3C02DF
X-Postfix-Sender: rfc822; ***@pahlevanzadeh.net
Arrival-Date: Tue, 9 Jun 2020 18:12:41 -0400 (AST)

Final-Recipient: rfc822; ***@gmail.com
Original-Recipient: rfc822;***@gmail.com
Action: failed
Status: 5.7.26
Remote-MTA: dns; gmail-smtp-in.l.google.com
Diagnostic-Code: smtp; 550-5.7.26 This message does not have authentication
information or fails to 550-5.7.26 pass authentication checks. To best
protect our users from spam, the 550-5.7.26 message has been blocked.
Please visit 550-5.7.26
https://support.google.com/mail/answer/81126#authentication for more 550
5.7.26 information. j14si2787252qvx.139 - gsmtp

salaam10.eml
Subject:
salaam10
From:
Mohsen Pahlevanzadeh <***@pahlevanzadeh.net>
Date:
6/10/20, 2:42 AM
To:
Pahlevanzadeh <***@gmail.com>

salaam10

#################################################################

But I authenticate on SMTP, My main.cf is :
broken_sasl_auth_clients = yes
command_directory = /usr/local/sbin
compatibility_level = 2
daemon_directory = /usr/local/libexec/postfix
data_directory = /var/db/postfix
debug_peer_level = 2
debugger_command = PATH=/bin:/usr/bin:/usr/local/bin:/usr/X11R6/bin ddd $daemon_directory/$process_name $process_id & sleep 5
home_mailbox = Maildir/
html_directory = /usr/local/share/doc/postfix
inet_interfaces = all
inet_protocols = ipv4
mail_owner = postfix
mailq_path = /usr/local/bin/mailq
manpage_directory = /usr/local/man
meta_directory = /usr/local/libexec/postfix
mydomain = pahlevanzadeh.net
myhostname = mail.pahlevanzadeh.net
mynetworks_style = host
myorigin = $mydomain
newaliases_path = /usr/local/bin/newaliases
queue_directory = /var/spool/postfix
readme_directory = /usr/local/share/doc/postfix
sample_directory = /usr/local/etc/postfix
sendmail_path = /usr/local/sbin/sendmail
setgid_group = maildrop
shlib_directory = /usr/local/lib/postfix
smtpd_recipient_restrictions = permit_sasl_authenticated , permit_mynetworks, reject_unauth_destination
smtpd_relay_restrictions = permit_sasl_authenticated, permit_mynetworks, reject_unauth_destination
smtpd_sasl_auth_enable = yes
smtpd_sasl_path = private/auth
smtpd_sasl_security_options = noanonymous
smtpd_sasl_type = dovecot
smtpd_tls_auth_only = yes
smtpd_tls_cert_file = /usr/local/etc/postfix/server.crt
smtpd_tls_key_file = /usr/local/etc/postfix/myserver.key
smtpd_tls_loglevel = 1
smtpd_tls_received_header = yes
smtpd_tls_security_level = may
smtpd_tls_session_cache_timeout = 3600s
smtpd_use_tls = yes
tls_random_source = dev:/dev/urandom
unknown_local_recipient_reject_code = 550
virtual_alias_maps = hash:/usr/local/etc/postfix/virtual
virtual_gid_maps = static:1002
virtual_mailbox_base = /var/mail/vhosts
virtual_mailbox_domains = /usr/local/etc/postfix/virtual_domains
virtual_mailbox_maps = hash:/usr/local/etc/postfix/vmailbox
virtual_minimum_uid = 1002
virtual_uid_maps = static:1002

And my master.cf is :

smtp inet n - n - - smtpd
pickup unix n - n 60 1 pickup
cleanup unix n - n - 0 cleanup
qmgr unix n - n 300 1 qmgr
tlsmgr unix - - n 1000? 1 tlsmgr
rewrite unix - - n - - trivial-rewrite
bounce unix - - n - 0 bounce
defer unix - - n - 0 bounce
trace unix - - n - 0 bounce
verify unix - - n - 1 verify
flush unix n - n 1000? 0 flush
proxymap unix - - n - - proxymap
proxywrite unix - - n - 1 proxymap
smtp unix - - n - - smtp
relay unix - - n - - smtp
-o syslog_name=postfix/$service_name
showq unix n - n - - showq
error unix - - n - - error
retry unix - - n - - error
discard unix - - n - - discard
local unix - n n - - local
virtual unix - n n - - virtual
lmtp unix - - n - - lmtp
anvil unix - - n - 1 anvil
scache unix - - n - 1 scache
postlog unix-dgram n - n - 1 postlogd
submission inet n - n - - smtpd
-o syslog_name=postfix/submission
-o smtpd_tls_security_level=encrypt
-o smtpd_sasl_auth_enable=yes
-o smtpd_reject_unlisted_recipient=no
-o smtpd_recipient_restrictions=permit_sasl_authenticated,reject
-o milter_macro_daemon_name=ORIGINATING

Where is my problem?

Oscar Renan

2021-03-22 04:07:18 UTC

Permalink

Post by Mohsen Pahlevanzadeh
##########################################################
This is the mail system at host mail.pahlevanzadeh.net.
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
said: 550-5.7.26 This message does not have authentication information or
fails to 550-5.7.26 pass authentication checks. To best protect our users
from spam, the 550-5.7.26 message has been blocked. Please visit 550-5.7.26
https://support.google.com/mail/answer/81126#authentication for more 550
5.7.26 information. j14si2787252qvx.139 - gsmtp (in reply to end of DATA
command)
Reporting-MTA: dns; mail.pahlevanzadeh.net
X-Postfix-Queue-ID: 3FBAA3C02DF
Arrival-Date: Tue, 9 Jun 2020 18:12:41 -0400 (AST)
Action: failed
Status: 5.7.26
Remote-MTA: dns; gmail-smtp-in.l.google.com
Diagnostic-Code: smtp; 550-5.7.26 This message does not have authentication
information or fails to 550-5.7.26 pass authentication checks. To best
protect our users from spam, the 550-5.7.26 message has been blocked.
Please visit 550-5.7.26
https://support.google.com/mail/answer/81126#authentication for more 550
5.7.26 information. j14si2787252qvx.139 - gsmtp
salaam10.eml
salaam10
6/10/20, 2:42 AM
salaam10
#################################################################
broken_sasl_auth_clients = yes
command_directory = /usr/local/sbin
compatibility_level = 2
daemon_directory = /usr/local/libexec/postfix
data_directory = /var/db/postfix
debug_peer_level = 2
debugger_command = PATH=/bin:/usr/bin:/usr/local/bin:/usr/X11R6/bin ddd $daemon_directory/$process_name $process_id & sleep 5
home_mailbox = Maildir/
html_directory = /usr/local/share/doc/postfix
inet_interfaces = all
inet_protocols = ipv4
mail_owner = postfix
mailq_path = /usr/local/bin/mailq
manpage_directory = /usr/local/man
meta_directory = /usr/local/libexec/postfix
mydomain = pahlevanzadeh.net
myhostname = mail.pahlevanzadeh.net
mynetworks_style = host
myorigin = $mydomain
newaliases_path = /usr/local/bin/newaliases
queue_directory = /var/spool/postfix
readme_directory = /usr/local/share/doc/postfix
sample_directory = /usr/local/etc/postfix
sendmail_path = /usr/local/sbin/sendmail
setgid_group = maildrop
shlib_directory = /usr/local/lib/postfix
smtpd_recipient_restrictions = permit_sasl_authenticated , permit_mynetworks, reject_unauth_destination
smtpd_relay_restrictions = permit_sasl_authenticated, permit_mynetworks, reject_unauth_destination
smtpd_sasl_auth_enable = yes
smtpd_sasl_path = private/auth
smtpd_sasl_security_options = noanonymous
smtpd_sasl_type = dovecot
smtpd_tls_auth_only = yes
smtpd_tls_cert_file = /usr/local/etc/postfix/server.crt
smtpd_tls_key_file = /usr/local/etc/postfix/myserver.key
smtpd_tls_loglevel = 1
smtpd_tls_received_header = yes
smtpd_tls_security_level = may
smtpd_tls_session_cache_timeout = 3600s
smtpd_use_tls = yes
tls_random_source = dev:/dev/urandom
unknown_local_recipient_reject_code = 550
virtual_alias_maps = hash:/usr/local/etc/postfix/virtual
virtual_gid_maps = static:1002
virtual_mailbox_base = /var/mail/vhosts
virtual_mailbox_domains = /usr/local/etc/postfix/virtual_domains
virtual_mailbox_maps = hash:/usr/local/etc/postfix/vmailbox
virtual_minimum_uid = 1002
virtual_uid_maps = static:1002
smtp inet n - n - - smtpd
pickup unix n - n 60 1 pickup
cleanup unix n - n - 0 cleanup
qmgr unix n - n 300 1 qmgr
tlsmgr unix - - n 1000? 1 tlsmgr
rewrite unix - - n - - trivial-rewrite
bounce unix - - n - 0 bounce
defer unix - - n - 0 bounce
trace unix - - n - 0 bounce
verify unix - - n - 1 verify
flush unix n - n 1000? 0 flush
proxymap unix - - n - - proxymap
proxywrite unix - - n - 1 proxymap
smtp unix - - n - - smtp
relay unix - - n - - smtp
-o syslog_name=postfix/$service_name
showq unix n - n - - showq
error unix - - n - - error
retry unix - - n - - error
discard unix - - n - - discard
local unix - n n - - local
virtual unix - n n - - virtual
lmtp unix - - n - - lmtp
anvil unix - - n - 1 anvil
scache unix - - n - 1 scache
postlog unix-dgram n - n - 1 postlogd
submission inet n - n - - smtpd
-o syslog_name=postfix/submission
-o smtpd_tls_security_level=encrypt
-o smtpd_sasl_auth_enable=yes
-o smtpd_reject_unlisted_recipient=no
-o smtpd_recipient_restrictions=permit_sasl_authenticated,reject
-o milter_macro_daemon_name=ORIGINATING
Where is my problem?

onde está o arquivo com os e-mail com suas senhas individuais e onde informa a senha para este usuário?
Faca mesmo enviando com senhas erradas. ele vai enviar sem autenticar a senha.

Johann Beretta

2021-05-21 20:06:01 UTC

Permalink

Well, part of your problem is that your mail hostname does not resolve
in both directions, equally.

i.e.

$nslookup mail.pahlevanzadeh.net

Name: mail.pahlevanzadeh.net
Address: 162.223.88.49

But.......

$ nslookup 162.223.88.49
49.88.223.162.in-addr.arpa name = host.coloup.com.

If you want gmail to accept your mails, then 162.223.88.49 should
resolve to mail.pahlevanzadeh.net

I don't know if there are other issues, but that one needs to be fixed
first.

Rick Cooper

2022-04-27 20:23:36 UTC

Permalink

Post by Johann Beretta

Well, part of your problem is that your mail hostname does not resolve
in both directions, equally.
i.e.
$nslookup mail.pahlevanzadeh.net
Name: mail.pahlevanzadeh.net
Address: 162.223.88.49
But.......
$ nslookup 162.223.88.49
49.88.223.162.in-addr.arpa name = host.coloup.com.
If you want gmail to accept your mails, then 162.223.88.49 should
resolve to mail.pahlevanzadeh.net
I don't know if there are other issues, but that one needs to be fixed
first.

I see this periodically as recent as yesterday. I got the same email that gmail rejected (corporate mailing) and
DNS symmetrical
SPF pass
DKIM pass
DMARK pass
we use mta-sts and are fully PCI compliant and yet gmail rejected the email out right. Every time I have checked this has been the case. But it's usually when HR is sending a mailing and there might be a dozen gmail addresses in that mailing. I personally believe it has to do with that because 2 of the 8 gmail addresses were rejected as above (again one mailing, same server and I believe gmail allows pipelining so they would have all been down the same connection and 2 of 8 say improper authentication and the other 6 are fine. I have brought this up with gmail multiple times but get no response so I have instructed those employees to consider a new personal email provider because it's not possible for us to influence gmail's attitude about their user issues and not receiving important emails. Had one employee who said he spent 3 days trying to run down gmail support and got no where. So with gmail it would appear you get what you pay for in terms of service and help. Of the 31 attempted phishing emails that hit our 5 servers in the last 24 (all were caught and quarantined for inspection) hours 26 originated from gmail accounts with full DMARC pass, just so you know. How about gmail look into stopping the outbound malicious emails before they block perfectly legitimate and important emails from properly configured mtas?

Muhammad Faizan Hanif

2022-06-06 08:59:56 UTC

Permalink

Post by Rick Cooper

Post by Johann Beretta

Well, part of your problem is that your mail hostname does not resolve
in both directions, equally.
i.e.
$nslookup mail.pahlevanzadeh.net
Name: mail.pahlevanzadeh.net
Address: 162.223.88.49
But.......
$ nslookup 162.223.88.49
49.88.223.162.in-addr.arpa name = host.coloup.com.
If you want gmail to accept your mails, then 162.223.88.49 should
resolve to mail.pahlevanzadeh.net
I don't know if there are other issues, but that one needs to be fixed
first.

I was having the same problem.

I just add ipv:4 in my SPF record and everything works fine.

I do not even have DKIM OR DMARK setup.

This is what my spf record now looks like.

v=spf1 a:mail.domainname.com ip4:000.000.000.000 ~all

I hope it will help you all.

Muhammad Faizan Hanif

2022-06-06 08:47:04 UTC

Permalink

I was having the same problem.

I just add ipv:4 in my SPF record and everything works fine.

I do not even have DKIM OR DMARK setup.

I hope it will help you all.

Scott Green

2022-06-06 23:37:23 UTC

Permalink

Hello, how did you resolve the issue?

Giuseppe Carella

2022-08-13 10:53:51 UTC

Permalink

can you explain better how to solve the problem? can you share a video?

Post by Scott Green

Hello, how did you resolve the issue?