Hi,

> > >     This was rejected by "reject_unauth_destination".
> >
> > Thank you so much. I had included my smtpd_recipient_restrictions
> > earlier in this thread, but should have been more complete. This is
> > the multi-instance postfix you helped me configure some time ago. Mail
> > is first processed by this postfix-117 instance, sent to amavisd, then
> > forwarded to postfix-out where it's sent to the recipient.
>
> One would expect to find anti-relay policies only at the input stage,
> with the downstream output instance(s) accepting all mail sent by the
> upstream instance(s).
>
> Is the below the configuration of the input or output instance?

This is from the input instance.

> > mydestination =
> > relay_domains = $mydestination, example.com, nnnhelp.zendesk.com
>
> Addresses in "relay_domains" would typically be accepted.  Is
> "nnnhelp.zendesk.com" verbatim the domain that's getting refused?

I'm sorry for all the obfuscation. Here is the real info:

May 12 23:01:18 xavier postfix-117/smtpd[3481869]: NOQUEUE: reject:
RCPT from mail-mw2nam10lp2104.outbound.protection.outlook.com[104.47.55.104]:
554 5.7.1 <members...@smartmlshelp.zendesk.com>: Relay access denied;
from=<> to=<members...@smartmlshelp.zendesk.com> proto=ESMTP
helo=<NAM10-MW2-obe.outbound.protection.outlook.com>

I believe I solved this part by adding smartmlshelp.zendesk.com to
relay_domains.

We've created an outbound O365 connector to route outbound mail
through our servers before being delivered to their final destination
- I believe this is effectively relaying mail from
outbound.protection.outlook.com:

May 12 23:04:00 xavier postfix-117/smtpd[3482092]: NOQUEUE: reject:
RCPT from mail-mw2nam12lp2048.outbound.protection.outlook.com[104.47.66.48]:
554
5.7.1 <u...@gmail.com>: Relay access denied; from=<u...@smartmls.com>
to=<u...@gmail.com> proto=ESMTP
helo=<NAM12-MW2-obe.outbound.protection.outlook.com>

This outbound connector process is described here (option 3):
https://docs.microsoft.com/en-us/Exchange/mail-flow-best-practices/how-to-set-up-a-multifunction-device-or-application-to-send-email-using-microsoft-365-or-office-365
> > smtpd_recipient_restrictions =
> >     reject_non_fqdn_recipient,
> >     reject_non_fqdn_sender,
> >     reject_unlisted_recipient,
> >     reject_unknown_recipient_domain,
> >     permit_mynetworks,
> >     reject_unauth_destination,
>
> This should not reject domains listed in $relay_domains.  Any
> relevant overrides in master.cf?  (See "postconf -Mf" output).

# postconf -c /etc/postfix-117 -Mf
policy-spf unix  -       n       n       -       -       spawn user=nobody
    argv=/usr/libexec/postfix/policyd-spf
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

> > /etc/postfix-117/nnnhelp-zendesk:
> >    /example\.com$/                permit
>
> Use of a PCRE table for relay control is a bad idea.  The above matches
> more domains than you actually intended.  The "relay_domains" setting
> should be enough.  [ I assume it is not actually "example.com"... ]

I've tried with cdb (my default db) but unsure how to do wildcards.

/etc/postfix-117/smartmls-com
# cat smartmls
/smartmls.com/          permit
j...@smartmls.com                permit

# postmap smartmls
# postmap -c /etc/postfix-117 -q j...@smartmls.com cdb:/etc/postfix-117/smartmls
permit

> What is your (built-in default?) setting of "smtpd_relay_restrictions"?

# postconf -c /etc/postfix-117 smtpd_relay_restrictions
smtpd_relay_restrictions = ${{$compatibility_level} < {1} ? {} :
{permit_mynetworks, permit_sasl_authenticated,
defer_unauth_destination}}

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