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I have a customer attempting to use postfix to send emails with SMTP. It appears that postfix will parse the email attributes correctly, but before sending the email it begins processing it again. This happens in an endless loop. I've put postfix into debug mode and produced a log file that looks almost exactly the same as a log file produced with my own system up to the point where it repeats the parsing of the email.

The customer's end-of-log:

postfix/smtpd[29586]: connection closed postfix/smtpd[29586]: connection established

My end-of-log:

postfix/smtpd[20539]: connection closed postfix/smtp[20543]: 0D65814D: to=<[email protected]>, relay=10.2.253.96[10.2.253.96]:25, delay=0.17, delays=0.03/0.07/0/0.06, dsn=2.0.0, status=sent (250 2.0.0 Ok: queued as O) postfix/qmgr[19812]: 0D65814D: removed

The main.cf file has

mydomain = localhost alias_maps = hash:/etc/aliases queue_directory = /var/spool/postfix command_directory = /usr/sbin daemon_directory = /usr/libexec/postfix mail_owner = postfix myorigin = $mydomain unknown_local_recipient_reject_code = 550 mynetworks = 127.0.0.0/8, [::1]/128 debug_peer_level = 2 sendmail_path = /usr/sbin/sendmail newaliases_path = /usr/bin/newaliases mailq_path = /usr/bin/mailq setgid_group = postdrop html_directory = no manpage_directory = /usr/local/man sample_directory = /etc/postfix readme_directory = no virtual_mailbox_domains = sciencelogic.em7 virtual_mailbox_base = /var/mail virtual_mailbox_maps = hash:/etc/postfix/silo.virtual-mailbox virtual_uid_maps = hash:/etc/postfix/silo.virtual-uid virtual_gid_maps = hash:/etc/postfix/silo.virtual-gid mailbox_size_limit = 0 relayhost = authnz.proofpoint.com:587 smtp_sasl_auth_enable = yes smtp_sasl_password_maps = hash:/etc/postfix/smtp_password smtpd_recipient_restrictions = permit_mynetworks local_recipient_maps =

There is no information about the email being rejected in the queue log. Running mailq > mailqueue.txt did not produce any meaningful information. I've also had the customer flush the queue with postqueue -f and restart postfix, but nothing has helped.

What is causing postfix to repeat parsing the email instead of sending it?

EDIT:

The master.cf file states (shortened for space to remove all commented-out lines):

smtp inet n - n - - smtpd -v 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 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

EDIT:

postqueue -p produces:

[root@sc-sl02-lab01 ~]# postqueue -p -Queue ID- --Size-- ----Arrival Time---- -Sender/Recipient------- 8687E226F6E* 936 Tue May 10 19:46:06 [email protected] [email protected] 88630226F70* 935 Tue May 10 19:46:06 [email protected] [email protected] 92456226F71* 933 Tue May 10 19:46:06 [email protected] [email protected] E0986226F74* 942 Tue May 10 19:46:06 [email protected] [email protected] EF72C36B12* 930 Tue May 10 19:46:06 [email protected] [email protected] F1631226F78* 930 Tue May 10 19:46:06 [email protected] [email protected] 3DE91226F77* 3072 Tue May 10 19:46:11 MAILER-DAEMON [email protected]

sudo postcat -qhbe 3DE91226F77:

-- 40 Kbytes in 17 Requests. [root@sc-sl02-lab01 ~]# sudo postcat -qhbe 3DE91226F77 *** ENVELOPE RECORDS active/3DE91226F77 *** message_size: 3072 221 1 0 3072 message_arrival_time: Tue May 10 19:46:11 2022 create_time: Tue May 10 19:46:11 2022 named_attribute: log_message_origin=local named_attribute: trace_flags=0 sender: original_recipient: [email protected] recipient: [email protected] *** MESSAGE CONTENTS active/3DE91226F77 *** Received: by sc-sl02-lab01.localhost (Postfix) id 3DE91226F77; Tue, 10 May 2022 19:46:11 +0000 (UTC) Date: Tue, 10 May 2022 19:46:11 +0000 (UTC) From: [email protected] (Mail Delivery System) Subject: Undelivered Mail Returned to Sender To: [email protected] Auto-Submitted: auto-replied MIME-Version: 1.0 Content-Type: multipart/report; report-type=delivery-status; boundary="0A32B226F7D.1652211971/sc-sl02-lab01.localhost" Message-Id: <[email protected]> This is a MIME-encapsulated message. --0A32B226F7D.1652211971/sc-sl02-lab01.localhost Content-Description: Notification Content-Type: text/plain; charset=us-ascii This is the mail system at host sc-sl02-lab01.localhost. 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 <[email protected]>: host authnz.prod-c15a-awsuse.proofpoint.com[205.220.189.150] said: 530 5.7.0 Authentication required (in reply to MAIL FROM command) --0A32B226F7D.1652211971/sc-sl02-lab01.localhost Content-Description: Delivery report Content-Type: message/delivery-status Reporting-MTA: dns; sc-sl02-lab01.localhost X-Postfix-Queue-ID: 0A32B226F7D X-Postfix-Sender: rfc822; [email protected] Arrival-Date: Tue, 10 May 2022 19:46:07 +0000 (UTC) Final-Recipient: rfc822; [email protected] Original-Recipient: rfc822;[email protected] Action: failed Status: 5.7.0 Remote-MTA: dns; authnz.prod-c15a-awsuse.proofpoint.com Diagnostic-Code: smtp; 530 5.7.0 Authentication required --0A32B226F7D.1652211971/sc-sl02-lab01.localhost Content-Description: Undelivered Message Content-Type: message/rfc822 Return-Path: <[email protected]> Received: from [172.16.0.1] (localhost [IPv6:::1]) by sc-sl02-lab01.localhost (Postfix) with ESMTP id 0A32B226F7D for <[email protected]>; Tue, 10 May 2022 19:46:07 +0000 (UTC) MIME-Version: 1.0 Content-Type: text/plain; charset="us-ascii" Content-Transfer-Encoding: 7bit Subject: MAJOR Event: Load average alert, (Load-15) state: (True) is running above the threshold of (None) From: EM7 LAB Event Notifier<[email protected]> To: CC: X-Priority: 3 Date: Tue, 10 May 2022 19:46:07 +0000 Message-Id: <[email protected]> Severity: MAJOR First Occurred: 2022-05-09 11:48:18 UTC Last Occurred: 2022-05-10 19:44:22 UTC Occurrences: 954 Source: Dynamic Organization: ScienceLogic Org Device: sc-sl01-db01 Message: Load average alert, (Load-15) state: (True) is running above the threshold of (None) Sent by Automation Action: Send Email External View this event at: http://em7.mydomain.com/em7/index.em7?exec=events&q_type=aid&q_arg=3988100&q_sev=1&q_sort=0&q_oper=0 --0A32B226F7D.1652211971/sc-sl02-lab01.localhost-- *** HEADER EXTRACTED active/3DE91226F77 *** *** MESSAGE FILE END active/3DE91226F77 *** [root@sc-sl02-lab01 ~]# sudo postcat -qhbe 14CBC226F76 *** ENVELOPE RECORDS active/14CBC226F76 *** message_size: 2962 220 1 0 2962 message_arrival_time: Tue May 10 19:46:10 2022 create_time: Tue May 10 19:46:10 2022 named_attribute: log_message_origin=local named_attribute: trace_flags=0 sender: original_recipient: [email protected] recipient: [email protected] *** MESSAGE CONTENTS active/14CBC226F76 *** Received: by sc-sl02-lab01.localhost (Postfix) id 14CBC226F76; Tue, 10 May 2022 19:46:10 +0000 (UTC) Date: Tue, 10 May 2022 19:46:10 +0000 (UTC) From: [email protected] (Mail Delivery System) Subject: Undelivered Mail Returned to Sender To: [email protected] Auto-Submitted: auto-replied MIME-Version: 1.0 Content-Type: multipart/report; report-type=delivery-status; boundary="000EC226F79.1652211970/sc-sl02-lab01.localhost" Message-Id: <[email protected]> This is a MIME-encapsulated message. --000EC226F79.1652211970/sc-sl02-lab01.localhost Content-Description: Notification Content-Type: text/plain; charset=us-ascii This is the mail system at host sc-sl02-lab01.localhost. 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 <[email protected]>: host authnz.prod-c15a-awsuse.proofpoint.com[205.220.189.192] said: 530 5.7.0 Authentication required (in reply to MAIL FROM command) --000EC226F79.1652211970/sc-sl02-lab01.localhost Content-Description: Delivery report Content-Type: message/delivery-status Reporting-MTA: dns; sc-sl02-lab01.localhost X-Postfix-Queue-ID: 000EC226F79 X-Postfix-Sender: rfc822; [email protected] Arrival-Date: Tue, 10 May 2022 19:46:06 +0000 (UTC) Final-Recipient: rfc822; [email protected] Original-Recipient: rfc822;[email protected] Action: failed Status: 5.7.0 Remote-MTA: dns; authnz.prod-c15a-awsuse.proofpoint.com Diagnostic-Code: smtp; 530 5.7.0 Authentication required --000EC226F79.1652211970/sc-sl02-lab01.localhost Content-Description: Undelivered Message Content-Type: message/rfc822 Return-Path: <[email protected]> Received: from [172.16.0.1] (localhost [IPv6:::1]) by sc-sl02-lab01.localhost (Postfix) with ESMTP id 000EC226F79 for <[email protected]>; Tue, 10 May 2022 19:46:06 +0000 (UTC) MIME-Version: 1.0 Content-Type: text/plain; charset="us-ascii" Content-Transfer-Encoding: 7bit Subject: MAJOR Event: Device Service Risk is High: 75 From: EM7 LAB Event Notifier<[email protected]> To: CC: X-Priority: 3 Date: Tue, 10 May 2022 19:46:06 +0000 Message-Id: <[email protected]> Severity: MAJOR First Occurred: 2022-05-09 01:00:16 UTC Last Occurred: 2022-05-10 19:45:18 UTC Occurrences: 172 Source: Internal Organization: System Device: test device service Message: Device Service Risk is High: 75 Sent by Automation Action: Send Email External View this event at: http://em7.mydomain.com/em7/index.em7?exec=events&q_type=aid&q_arg=3987958&q_sev=1&q_sort=0&q_oper=0 --000EC226F79.1652211970/sc-sl02-lab01.localhost-- *** HEADER EXTRACTED active/14CBC226F76 *** *** MESSAGE FILE END active/14CBC226F76 ***
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  • Please add your postfix configuration as recommended in the tag, and an example of how the message appears in the queue, both might contain helpful clues. (use postqueue -p to list, use postcat -qhbe QID to review a single entry, and get more context in logs to distinguish the sender just sending the message multiple times from a malfunction on your end). Commented May 3, 2022 at 4:42
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    Other than the odd domains I don't see anything immediately obvious in your config. Where are you getting that "It appears that" idea from. Please share more log context and a sample message as it appears in the queue, there may actually be a clue as to what exactly postfix is doing. Commented May 11, 2022 at 14:53
  • Please see the edited post that includes the master.cf file. The main.cf file is the postfix configuration. I also included the postqueue -p and postcat -qhbe commands. Commented May 11, 2022 at 14:53
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    What's the 10.2.253.96? Commented May 11, 2022 at 15:00
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    Unrelated, but you should probably fix that localhost bit. Names clearly belonging to locally-administered naming schemes/roots? A-OK. But receiving mail from localhost.localhost containing little information which originator/relay is associated with which org/branch/room/machine? Very annoying to anyone diagnosing mail issues in the future! Commented May 11, 2022 at 15:27

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authnz.prod-c15a-awsuse.proofpoint.com[205.220.189.150] said: 530 5.7.0 Authentication required (in reply to MAIL FROM command)

That sounds a lot like you are not authenticating to the relay you have configured.

relayhost = authnz.proofpoint.com:587 smtp_sasl_auth_enable = yes smtp_sasl_password_maps = hash:/etc/postfix/smtp_password

Check the contents of /etc/postfix/smtp_password. Specifically, postfix instruct you to match the format between relayhost value and map lookup key.

If you specify a non-default TCP Port (such as ":submission" or ":587") in the relayhost destination, then you must use the same form in the smtp_sasl_password_maps file.

If this turns out to indeed be a problem with that password map, don't forget to update the indexed cache by issuing postmap /etc/postfix/smtp_password - and consider what should happen to the yet-to-be-delivered messages in your queue, you may want to update the affected recipients and senders through some other route than delivering (possibly a lot) non-delivery notifications.

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