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Exchange not routing messages to new server

Posted on 2011-09-02
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Last Modified: 2012-05-12
I have deployed a new Exchange 2007 server in to an existing Exchange 2003 setup.  Everything seems to have installed correctly and the servers see each other as there are 2 administrative groups not visible.  The bridgehead connectors were auto-created and I am able to move mailboxes across to the new server.  Problem is that when an inbound message comes in to a mailbox that is located on the new server, it gets stuck in the "2003SERVER-2007SERVER (Routing Group Connector)" or "Messages queued for deferred delivery" in the queue.  My default SMTP Connector in Exchange 2003 was set to deliver through a smart host but I've tried switching that back to DNS but with no luck.  All other messages inbound/outbound work on the 2003 server but can't seem to get anything to route to the 2007 server.

What am I missing to get this to work?  
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Question by:K2NS
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Expert Comment

by:Jian An Lim
ID: 36477608
Get-RoutingGroupConnector| FL

did you able to send email from ex07 to ex03 ?

smarthost is definitely a complex a bit the issues (and when you change your smart host, you need to restart your smtp services)

suggest you to read

http://forums.msexchange.org/Exchange_2003_cannot_send_to_Exchange_2007/m_1800432360/tm.htm
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Author Comment

by:K2NS
ID: 36478499
No, local email is not going in either direction.  Both servers can send out directly for external email using DNS or Smart Host.  I've gone through the article to check if it the RGC are bi-directional and they are.  I've also deleted and recreated them using the EMS in 2007 with no luck.
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Author Comment

by:K2NS
ID: 36478586
OK... I've gotten a bit further... I can now receive messages send from 2003 to 2007 server.  Just not the other way.  External email is deliverable from both servers using DNS or Smart Host.  
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Expert Comment

by:Jian An Lim
ID: 36479170
can you run the best practice analyzer and mail flow checker and verify everything is on track?
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Accepted Solution

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jabri007 earned 250 total points
ID: 36482572
Hello,

Please create 2 seperate one way routing group connector (RGC) between Ex2003 to Ex2007 from Exchange 2003 Server and one way RGC from Exchange 2007 to Ex2003 from Exchange 2007 Server

You may get the Message that "Remote host not responding or timed out" in that Queue

Even i had the same issue  so creating one way RGC between servers resolved it

Regards
Mahmood
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Author Comment

by:K2NS
ID: 36486868
Ok... I've almost got this solved... I now know why email would not work from 2007 to 2003.  It is because the default port for the SMTP Virtual Server in our 2003 server is set to port 24 (the front end spam application is processing mail on 25).  If I change the port back to 25, the email delivery works.  But I can't leave it like that or our front end spam filter is useless.

My question is now is to determine how to re-program the RGC so that the 2007 server will deliver to the 2003 server on port 24.
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Expert Comment

by:Jian An Lim
ID: 36487046
I will suggest you to sort out what is your front end spam application doing on that port ..

what application is thaT?
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Author Comment

by:K2NS
ID: 36487073
AltN SecurityGateway is installed on the same server and requires port 25 to process email.  I guess I could port translate 25 on the front-end router to a different internal port and put Exchange back to 25.  But their setup instructions is to modify Exchange to port 24 and their app takes over 25.  
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Expert Comment

by:Jian An Lim
ID: 36487158
okay, i never know any product need to take over port 25, usually they can tap into the server and do the scanning. but i could be wrong.

Front end firewall relay to different port definitely helps :)
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Author Comment

by:K2NS
ID: 36487355
Actually, I've used several different applications which listen on port 25, process the spam and then forward the messages through to the SMTP connector listening on another port.  I know some that tap right in but this particular customer uses this application.  I'll have to see if there is any implications switching inbound smtp traffic to translate to a different port internally but the idea is sound.  What might not work is once the front end application is set to use a different port, whether Exchange will forward the message through to that new port to process the outbound message as well.  I may wind up with the same type of issue but with outbound delivery.  I'll have to test this out.  I think I could also setup the second NIC with another internal IP address so that I can separate both to use services under port 25 (I think).
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Expert Comment

by:Jian An Lim
ID: 36487416
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Assisted Solution

by:Jian An Lim
Jian An Lim earned 250 total points
ID: 36487431
it was written that although this is technically possible to do, Microsoft said it would be inadvisable and unsupported.
so better to stay away from there.
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Author Closing Comment

by:K2NS
ID: 36513879
Ok... I got everything to work but it took a little work.  I moved our spam filtering application on the a VM server so that I can return the server to port 25 on the Default SMTP Virtual Server.   After doing that, everything started to work.  Looking back on the situation, I guess I could have changed both servers SMTP to listen and send out on port 24 (then use the Exchange connector to forward to the smarthost listening on port 25).  

Thanks for your help in leading me in the right direction.
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