Exchange 2010: How (if possible) do I send a copy of sent emails to an external non-exchange server sharing the same domain name?

Hi there, I will try to explain what they asked me, I don't even know if it's possible to achieve.

We have an external mail server (not Exchange) where all the mailboxes are, and it's the one used as MX record, so the world will send emails to us to this server.

There is a rule on this server, so that every received email will be forwarded (a copy)  to our Exchange 2010 server (no MX record associated, the rule specifies the IP address).

Now, when people using OWA or Outlook send "internal" messages using Exchange, these messages will be delivered (I guess) using some sort of internal system, straight to the Exchange mailbox, leaving the external server out. Some people only use the external server, or would like to have a copy there. Is it possible to achieve this?

From what I can guess, if I forward an email to the external server, the mentioned rule would forward it again to Exchange?

The 2 servers share the same domain, so all mailboxes are like in both servers.

Can someone help me with this, please?
Thanks in advance,
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AkhaterConnect With a Mentor Commented:
it will for sure ....

looks like you are out of luck in your scenario
maraboshiAuthor Commented:
Thanks for the help, I already tried that and it doesn't work as I fact, from the article you linked:

"When you configure an accepted domain as an internal relay domain, Exchange first tries to deliver to a recipient in the Exchange organization. If the recipient isn't found, the message is routed to the Send connector that has the closest address space match."

That is: first tries to deliver to the Exchange organization...and since it will always find the user, as all of us have a mailbox defined there, it will stop and never send to the external server a "copy".

Does it make sense?

Thanks :-)
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oh yes now I understand what you mean.

DO you have an edge server by any chance ? or any kind of mail relay
maraboshiAuthor Commented:
Nope...the "internal" Exchange and the external "real" mail server (don't know what software they use) are the only 2 servers we have. I can install another Exchange as Edge server if that can help...but the external mail server must be the primary one, as it's the only one hosted in a proper service provider, with air conditioning, proper power supplies and so on.
an edge would solve your issue and it would be as follows

for each create a contact with email

then on your edge create an email rewrite policy to to

of course keep your send connector
maraboshiAuthor Commented:
Will check this later or tomorrow and let you know, thanks :-)
maraboshiAuthor Commented:
I was looking into the Edge server, I had one installed but not configured.

One thing before I waste time with the Edge: since there is a rule on the external non-Exchange server to forward a copy of every email to Exchange...wouldn't this result as a loop?

So: the external third party server is the MX defined one in charge for the domain.
I send an email to my organization from gmail for example.
The server has a rule to forward a copy to the IP address of the internal Exchange (no MX associated).

If I send an email from Exchange to Exchange...and the Edge forwards a copy to the external server, wouldn't the rule I mentioned before forward a copy again, back to Exchange?
maraboshiAuthor Commented:
I just needed an information to be sure of what I already thought rather than a technical explanation with steps and so on.
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