On Thu, Aug 05, 2021 at 05:56:54PM +0000, Gomes, Rich wrote:

> I can work with the linux team to have it tested and upgraded since I do not 
> control the OS portion of the servers.
> I did postmap the transport file to no avail.
> 
> Here is the results of postfix -n:
> 
> mydestination =
> mydomain = domain.com
> myhostname = postfix.domain.com

I would typically set "$myorigin" explicitly, rather than rely on the
default "myorigin = $myhostname".

> readme_directory = /usr/share/doc/postfix-2.6.6/README_FILES
> sample_directory = /usr/share/doc/postfix-2.6.6/samples

Given you're running Postfix 2.10, best to remove these outdated
settings.

> relay_domains = $myhostname, hash:/etc/postfix/relay_domains
> relayhost = [xxx.outlook.com]:25

These domains are handed off to the relay_transport barring a
match in transport_maps.

> sender_canonical_maps = regexp:/etc/postfix/sender_canonical

I don't recommend sender_canonical_maps, best to canonicalise
all addresses in the same way, e.g. both "From:" and "Cc:"
are addresses a recipient might reply to in a "Reply-All".

> transport_maps = hash:/etc/postfix/transport

Have you tested this table with 

    $ domain=<somedomain>
    $ postmap -q "$domain" hash:/etc/postfix/transport

> Anywhere else to look?

Your logs showing delivery of mail to some domain via some transport
other than what's in transpor_maps.  Also, any stray "content_filter"
settings in master.cf.

Post the output of "postconf -Mf" and some relevant logs.

-- 
    Viktor.

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