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SMTP relay in Exchange 2013 and display name

We have an Exchange 2013 on premise installation with 3 mailbox servers in a single dag and two cas servers configured as SMTP relay proxy servers. I have a receive connector for internal relay set up. TLS is selected for authentication and anonymous for permissions group. Scope is set to vLANs where servers reside.

I have created a contact object in AD for the SMTP address.

My problem is the translation of sender SMTP address to display name when relaying internally. This works inconsistently. When using telnet from one server (2008 R2) the display name shows correctly in outlook. When using postfix from a RHEL 6 server, outlook only shows the SMTP address and not the display name
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ict-admin
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ict-admin
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Simon Butler (Sembee)ConsultantCommented:
I have seen this before with Linux servers.
If you look at the headers of the messages you will see the To address is being formatted in a different way.

I expect it is setting the display name as the email address (so it is user@Example.com <user@example.com>) rather than just the plan email address as you would get with a telnet session. You would need to correct the Linux server to have a display name in the header for it to work correctly.

Simon.
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ict-adminAuthor Commented:
I have tested with four different methods. One from a server 2008 r2, another from the Linux postfix, a third from a windows 7 client (regular client), a fourth from a windows 7 client (admin client).

The first one works as expected
The second one does not work
The third does not work
The fourth works as expected

All messages have <sender@domain.com>  in the "From:" header field.

Looking at the message tracking logs, the only difference I can spot is the directionality. On the messages where the display name shows correctly, the directionality is "originating". On the messages where the display name is not shown correctly, the directionality is "incoming".

The servers are in networks that are scoped in a receive connector for internal relay. The clients fall under the default connector for internal relay.

edit: Telnet from the Linux server yields the same result as from postfix.
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Simon Butler (Sembee)ConsultantCommented:
When you are sending from a client, the behaviour will be different. Exchange treats internal and external traffic in different ways. It is effectively attempting to match the SMTP address with something in AD to "correct" the display name to match.
That is why you are seeing the different directionality listings.

Simon.
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ict-adminAuthor Commented:
But I get "incoming" from one client and the Linux and "originating" from another client and a windows server.
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