On Tue, Oct 26, 2021 at 04:22:53PM +0000, Cooper, Robert A wrote:

> Howdy!  We have noticed that certain email going through our outbound
> relay are ignoring the "relayhost = [smtp-relay.site.com]:25".

Sorry, that's not possible.  The delivery of messages for *all*
recipients uses the same transport resolution logic, which defaults
remote destinations to relayhost, barring explicit transport table
overrides, sender-dependent settings, ...

> The condition seems to be when a message has an envelope rewrite based
> on LDAP lookup (specifically, from site.com to email.site.com, which
> goes to gmail).

Then clearly you have explicit transport settings for "email.site.com".

> After the lookup and rewrite, Postfix appears to do an MX lookup to
> try and send directly to google and ignores the specified relayhost.

Because you have a transport entry for the recipient domain.

> Is there something else I'm missing? I've verified that there are no
> transports designated for mail.site.com that would override the
> relayhost.

Is it "mail.site.com" or "email.site.com"?  In either case, you
clearly do have such transport settings, so look harder.

    http://www.postfix.org/DEBUG_README.html#mail

For more detailed help include "postconf -nf" output in your reply
(without any rewrapping of lines).  Also include one or two log entries
for relevant messages, with at most the localparts of email addresses
obfuscated.  Do not change the domain names, if they are sufficiently
sensitive to not posted here, you'll need to find help elsewhere on
a commercial basis.

-- 
    Viktor.

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