I have read the many answers to many similar questions, but have not found exactly this question or any answer that helped.
I have a Postfix 2.11 server (mail-server.example.com
) that is strictly for outgoing email. It works fine if it is able to send the email on the first try. However, for performance reasons, if it cannot send the email on the first try and instead wants to defer it, I have configured smtp_fallback_relay
so that it forwards the email to another server (deferred-mail.example.com
) that handles only deferred emails.
smtp_fallback_relay = [deferred-mail.example.com]
If, from my trusted IP (mynetworks
), I send an email to either server destined for [email protected]
, either server will accept it and try to send it to Gmail. Because my server IP is new, Gmail rejects the email from either server with 421
(temporary deferral). As expected, the deferred-mail
server simply puts the message in its deferred queue and tries again later.
The weird part is that while mail-server
will send the message to Gmail to begin with, after receiving the 421
, it attempts to send the mail to deferred-mail
, but gives up and instead bounces the message, saying "mail for gmail.com loops back to myself". I see no logs on the deferred-mail
server saying anything about what is going on.
So both servers are configured to accept mail and relay it to Gmail if the client is trusted, and the deferred-mail
trusts mail-server
(I can send to a Gmail address when directly connecting to deferred-mail
from `mail-server), so how is Postfix coming up with this "loop" and why is it bouncing the email instead of relaying it?
Update and clarification about the logs below.
For privacy reasons, I am not posting the actual domain name or IP addresses we are using. Throughout this post and in the log excerpt below, I have replaced the actual root domain name we are using with example.com
.
This setup was copied from a working email cluster. I am confident that it is theoretically sound, and suspect it is just a matter of some setting not being correctly replaced or translated. It is just that with this odd behavior and seemingly incorrect error message, I cannot figure out what to change, and that is why I am asking for help.
- "Greeted me with my own hostname" is not a mistake or problem
When sending emails via SMTP, the sender begins by identifying itself by host name. Big mail processors like Gmail and Yahoo take several steps to assess the reputation of the sender. With IPv4, two of the first things they did were
- Record the IP address of the sender and build up a record of the quality and quantity of emails coming from that specific IP address
- Verify that the reverse DNS record for that IP address maps back to the host name the sender identified itself with
If the IP address has a bad reputation or the reverse DNS does not match the sender host name, the receiver would be much more likely to mark the email as Spam regardless of anything else.
For both these reasons, both mail-server.example.com
and deferred-mail.example.com
are behind the same NAT Gateway that
- Has a static IP address, so all email comes from the same IP address with the same reputation (
REDACTED-PUBLIC-IPv4
in the log excerpt below) - Has a reverse DNS record that identifies that IP address as
mail-server.example.com
For that reason, when deferred-mail.example.com
identifies itself in an SMTP session, it identifies itself as mail-server.example.com
. This is correct, desired behavior and not an uncommon situation for the reasons stated above. (deferred-mail.example.com
points to a private IP address, 10.111.14.181
in the logs below and does not have a reverse DNS record.)
- IPv6 failure is not a mistake or problem
Our server stack does not currently have IPv6 enabled. Because we are using a new domain name, we have zero domain reputation, so we want to stick to IP reputation until we have a solid domain reputation established. (Because IPv6 addresses are disposable, they will never be an adequate basis for reputation.)
Therefore, the failures to reach Gmail's IPv6 servers aspmx.l.google.com
and alt2.aspmx.l.google.com
are expected and not particularly a problem, although if there is a setting that I can set to keep postfix
from even trying to reach IPv6 addresses, please let me know so I can make that change.
Answer to disabling IPv6 attempts: Add this to your main.cf
inet_protocols = ipv4
Per request, here are redacted logs of the error:
postfix/smtpd[26668]: 50F7C5B81: client=ip-10-111-7-75.us-west-2.compute.internal[10.111.7.75]
postfix/cleanup[26682]: 50F7C5B81: message-id=<>
opendkim[36]: 50F7C5B81: can't determine message sender; accepting
postfix/qmgr[143]: 50F7C5B81: from=<REDACTED-SENDER>, size=279, nrcpt=1 (queue active)
postfix/smtp[26686]: 50F7C5B81: host aspmx.l.google.com[74.125.197.26] said: 421-4.7.0 [REDACTED-PUBLIC-IPv4 15] Our system has detected that this message is 421-4.7.0 suspicious ...
postfix/smtp[26686]: connect to aspmx.l.google.com[2607:f8b0:400e:c07::1a]:25: Cannot assign requested address
postfix/smtp[26686]: connect to alt2.aspmx.l.google.com[2607:f8b0:4001:c56::1a]:25: Cannot assign requested address
postfix/smtp[26686]: 50F7C5B81: host alt2.aspmx.l.google.com[142.250.152.27] said: 421-4.7.0 [REDACTED-PUBLIC-IPv4 15] Our system has detected that this message is 421-4.7.0 suspicious ...
postfix/smtp[26686]: warning: host deferred-mail.example.com[10.111.14.181]:25 greeted me with my own hostname mail-server.example.com
postfix/smtp[26686]: warning: host deferred-mail.example.com[10.111.14.181]:25 replied to HELO/EHLO with my own hostname mail-server.example.com
postfix/smtp[26686]: 50F7C5B81: to=<[email protected]>, relay=deferred-mail.example.com[10.111.14.181]:25, delay=26, delays=24/0.01/1.5/0, dsn=5.4.6, status=bounced (mail for gmail.com loops back to myself)
log messages here about sending bounce email to sender
have been removed
postfix/bounce[26688]: 50F7C5B81: sender non-delivery notification: AEA8A5B83
postfix/qmgr[143]: 50F7C5B81: removed