Emmett Culley via Postfix-users:
> I have a long time running Postfix server (version 2.10) where I need to send
> from specific IP addresses for some virtual domains.
>
> I have it working, sort of. If I send email from this server to another
> server running postfix, it all seems to work. The sent email shows the
> transport required IP address in the header and all is well. DMARC, SPF and
> DKIM all pass.
>
> However, most times I send an email from that server to any gmail account,
> that email is bounced with the following error from gmail:
>
>
> The IP address sending this message does not have
> a PTR 550-5.7.25 record setup, or the corresponding forward DNS entry
> does
> not point 550-5.7.25 to the sending IP. As a policy, Gmail does not
> accept
> messages from 550-5.7.25 IPs with missing PTR records. For more
> information, go to 550 5.7.25
>
> The email is sometime accepted, but put in the SPAM folder. When I look at
> the headers for the email sent to SPAM I see that it is not sent from the
> specified IP address. When checking the headers in the email that was
> successfully received by my other postfix server I see that that email is
> sent from the specified IP address, which is why it passes SFP and FQDN.
>
> Before I set up the transports to specify different IP addresses for some
> domains this was all working. The problem I am attempting to fix it that one
> of the domains sends out an opt-in newsletter three or four times a month,
> and so sometimes causes it's IP address to be placed on one or more RBLs. Of
> course when that happens all of the other email domains sending on that IP
> address fail spam checks. So we want to send the newsletters from their own
> IP address.
>
> In main.cf:
>
> myhostname = animalshelter.tld
> mydomain = animalshelter.tld
> mydestination = localhost, ###.##.##.40, ###.##.##.38
>
> sender_dependent_default_transport_maps = hash:/etc/postfix/sender_transport
Note that this mapping is based on the envelope.from address, not
based on header.from.
> In sender_transport:
>
> @newsletterdomain.tld domain_hm
> @animalshelter.tld domain_vo
> @dogtrainer.tld domain_vo
>
> In master.cf:
>
> domain_hm unix - - n - - smtp
> -o syslog_name=postfix-HM
> -o smtp_helo_name=newsletterdomain.tld
> -o smtp_bind_address=###.##.##.38
>
> ###.##.##.38:smtp inet n - n - - smtpd
> -o smtpd_sasl_auth_enable=no
> -o content_filter=amavisfeed:[127.0.0.1]:10040
>
> domain_vo unix - - n - - smtp
> -o syslog_name=postfix-VO
> -o smtp_helo_name=animalshelter.tld
> -o smtp_bind_address=###.##.##.40
>
> ###.##.##.40:smtp inet n - n - - smtpd
> -o smtpd_sasl_auth_enable=no
> -o content_filter=amavisfeed:[127.0.0.1]:10040
>
> I ran postmap sender_transport and restarted postfix.
>
> Note that when sending to my other postfix server I see "postfix-HM" in the
> this server's log, and when sending to gmail "postfix-HM" is not there.
>
> Sending from any of the other domain on that server to gmail seems to work
> OK. However, they all send from the animalshelter.tld host which is at
> ###.##.##.40, and that is that is the IP address that shows up in the
> received header as the sending IP address.
>
> I've been beating my head against this wall for a while. There is clearly
> something I am not understanding. Any help would be appreciated.
>
> TL;DR
>
> Why is mail received by gmail different than those received by Postfix.
First, verify that your sender_dependent_default_transport_maps is not
pre-empted by a higer-precedence mechanism:
* In order of decreasing precedence, the delivery transport is
taken from 1) $transport_maps, 2) $sender_dependent_default_transport_maps,
or $default_transport.
Then, the clue is in the from=<envelope.from> that Postfix logs for
those messages. The envelope.from address determines the transport_maps
entry, and by implication, the smtp_bind_address value.
Wietse
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