Exchange 2010 internal relay doesn't deliver email to local accounts

Our company has an Exchange 2010 server pulling email from a POP server that is internet facing.  We have users on the POP server as well as on the Exchange server that all share the same domain name.  Sending email from either server is no problem, but I can't get Exchange to send to users on the POP server.  It always comes back as user unknown, most likely because those users indeed are not on the Exchange server.

Is there a way to get Exchange to send to the users on the POP even though they're on the same domain?  I added an SMTP connector that delivers to the POP.  I tried setting the accepted domain to 'Internal Relay' but which worked, but then we couldn't deliver locally.

This setup used to work when we had Exchange 2003.
lilgoombaAsked:
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AkhaterCommented:
what you did is correct, you should set the common domain as "internal relay" instead of "authoritative" nothing else to do

what NDR did you get with that config?
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lilgoombaAuthor Commented:
There is no NDR, the email just seems to sit in the queue.  As soon as I switch it back to Authoritative, the mail gets delivered.  It seems like it wants to send everything meant for our domain out to the POP server.
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AkhaterCommented:
did u restart your smtp service after setting it to internal relay ?
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lilgoombaAuthor Commented:
I just restarted the transport service, and still nothing.  Set as internal relay, it delivers everywhere EXCEPT locally.
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AkhaterCommented:
the one that are supposed to be local are sitting in which queue ?
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lilgoombaAuthor Commented:
It's sitting on the Exchange 2010 server.

Another piece to the puzzle is that our 2003 server is still hooked up with most of the mailboxes on that machine.  Could this be causing some of the problems?

When I look at the stuck emails in que, it says that there is a local loop.  What does that mean?
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AkhaterCommented:
yea it could be

give me more details about ur email routing
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lilgoombaAuthor Commented:
The Exchange 2003 had the SMTP connector that went to the POP server, but it's been removed.  Both servers have a connector that links them to each other which was automatically created during the 2010 install.  Both Exchange servers also have outgoing SMTP connectors for direct internet bound traffic.

The 2003 server has the actual POP connector that pulls the mail to the local accounts.  That's the only reason it's still around.  If mail comes into the 2003 server, it either stores them locally or forwards them to the 2010 server.

I'm just not sure why, when I enable relaying, the local mail goes in a loop.
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AkhaterCommented:
the first thing to do is to remove the SMTP connector (sending) from the 2003 and let the Send Connector of 2010 handle all the outbound traffic
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lilgoombaAuthor Commented:
Actually, I'm sorry, it's not a connector on the 2003, it's using "Default SMTP Virtual Server".  I can't remove it, but I can stop it.  Will that tell Exchange to send all mail to the 2010 server to go out?
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AkhaterCommented:
no don't stop it.

so on exchange 2003 you only have the default smtp virtual server? by any chance is this guy configured with a smart host ?
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lilgoombaAuthor Commented:
No, there's no smart host listed under Delivery -> Advanced.

Unfortunately I wasn't involved with the original setup, so I'm sure there are settings here and there that I haven't discovered yet.
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lilgoombaAuthor Commented:
More info:  under the Mail tab, it has "Forward all mail with unresolved recipients to host" and then it has the POP server listed.
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AkhaterCommented:
alright the queue they are stuck into are they on the 2003 or 2010 server?

is your internal AD name the same as your SMTP domain ?

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lilgoombaAuthor Commented:
The queue is on the 2010 server (which is where most of the mailboxes aren't, as I'm discovering).  Our AD name is the same as the SMTP domain.
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AkhaterCommented:
"More info:  under the Mail tab, it has "Forward all mail with unresolved recipients to host" and then it has the POP server listed." can you remove this please restart the smtp and try again
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lilgoombaAuthor Commented:
Done.  It seemed to work for one email, then it stopped delivering locally.

Although, now I noticed that while in relay mode, mail gets sent to 2010 recipients, only not to the 2003 recipients.  They seem to get stuck on the 2010 server and go in a loop.
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AkhaterCommented:
can you confirm this finding ? can u make a series of test to confirm that users on 2010 can indeed receive emails ?

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lilgoombaAuthor Commented:
Confirmed.  When it's set to relay, everything works except mail doesn't make it to the old 2003 server.
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AkhaterCommented:
well it is kind of logic

once you set it to internal relay (for a reason I can't find now) the 2003 is sending everything to 2010.

2010 is discovering that that mailbox is on the 2003 and will try to send it back and that's the loop...

The question is why 2003 is sending everything to 2010?

My best guess is the difference between the mail recipient policies in 2003 and the accepted domains in 2007/2010.

your best bet is to move all your mailboxes to 2010
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lilgoombaAuthor Commented:
That's what I was afraid of...I'm doing that this weekend.  I was just hoping to have this work in the meantime.  

Thanks for all of your help, I really appreciate it.
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AkhaterCommented:
let's try one more thing please


how many recipient policies do you have ?
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lilgoombaAuthor Commented:
This was most likely a problem with having both Exchange 2003 and 2010 in the same organization.  Once we moved everyone to 2010, the problem went away and we're now able to send to the POP server.

Apparently the 2003 <-> 2010 connector will cause a loop in this situation, sending local emails between the two servers until they time out.
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