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Exchange 2010/2007 message transfer

Posted on 2011-03-21
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Last Modified: 2012-05-11
New guy here, let's see how good this is. I have already searched previous posts.

I have 2 different physical sites within the same organization. These sites are
connected internally via a T-1 with no firewall between them.  Each site has their
own Internet connection. Both sites are part of a single AD forest and single domain.
Each physical site has their own external Internet email domain.
Each Exchange server is self-contained (no Edge servers).

Site1: Orginal site of the orgainization, had Exchange 2000 which I just replaced
with Exchange 2010. Removal of Exchange 2000 and install of Exchange 2010 went fine.
Has a Win 2008 domain controller that is a global catalog. All mailboxes were moved from the
Exchange 2000 server to the Site2-Exchange 2007 server prior to uninstall of Exchange 2000.  
All of the decommissioning steps were taken in order to allow for install of Exchange 2010.

Site 2: Has Exchange 2007 SP2 (Rollup 5) server and Win 2003 domain controller that was the first domain controller in the domain.  

Site 1-Exchange 2010: EMC see’s all the mailboxes on the Exchange 2007 server, sees the config, etc. I successfully moved a test mailbox from 2007 to 2010. I have also created a new mailbox on 2010.

Problem description:  I cannot send email internally from mailboxes on either server to a mailbox on the other server.  
Internet email works correctly on both servers.  
OWA works on both servers, although I have not yet installed “real” SLL certs for the 2010 server.
Cross server email ends up in the message queue and eventually times out.  

I can ping each server from the other by FQDN name.
I have done a tracert to each server from the other, and the route is correct.
I can telnet from each server to the other on TCP port 25, and actually created a message via telnet on each server via SMTP.
I have tried disabling all but the default receive connectors (client & default)on both servers at the same time, restarted both transport services and tried messages again. That did not work either.

I’m sure this is something simple, but I cannot find it. Help.
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Question by:l8tech
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Accepted Solution

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Glen Knight earned 500 total points
ID: 35187397
Check the receive connectors on both servers and ensure that under the Permissions Groups tab that Exchange Servers is checked and that under the Authentication tab Exchange Server Authentication is enabled.
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Author Comment

by:l8tech
ID: 35188153
Thanks for the response.

These are checked on both servers. Probably too much info, but I have attached a Word doc with Receive Connector properties screen shots from both servers.

 Exchange-Server-Receive-Connecto.doc

Is there a way to emulate/verify Exchange Server authentication via telnet? As I said I can telnet to each server from the other server on port 25 and get a banner response, and get a HELO reponse indicating the IP of the server I am telneting from.  Can I use STARTTLS and AUTH commands to do this because I think the track of it being an authentication issue may be right given that SMTP communication seems to be working.

Thanks again.
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Expert Comment

by:Glen Knight
ID: 35188173
Out of interest, have you installed the SMTP service on either server? If so this needs to be removed.
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Author Closing Comment

by:l8tech
ID: 35188446
Your comment got me thinking more about authentication. I tried telnet STARTTLS and received a message indicating that the antivirus that the site uses may not be allowing TLS to start.  I disabled this AV mail scanning service on both servers and messages were delivered.  For future reference this site uses avast! anti-virus for servers and the mail scanner service stops TLS which then does not allow Exchange servers to communicate vis TLS. Probably could have disabled TLS in Exchange, but the AV is not really needed as email AV is done at the email gateways.  Thanks for getting my mind headed in the right direction.
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