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Exchange 2003 Inter-site mail delivery not working?

Posted on 2006-05-03
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Last Modified: 2013-11-15
Hi -

I am looking for troubleshooting ideas / possible suggestions on this problem:

Started with an existing Win2000 Server running Exchange 2003.  This server will be decommissioned soon -

So on the same domain I have built an additional Win2k3 box with Exchange 2003 Sp2.  Installed into the Exchange Organization no sweat...

The idea is : Move mailboxes when we migrate.

Created a test user on one server, moved to other server no problem.

But I can't get mail delivery to flow from a test mailbox on the new Exchange box back to a test mailbox on the old.  It works the other way.  When looking in the queues, I can see the messages and they just hang there.  

I've turned on logging, but I'm not certain what information can be learned from this.  I've never troubleshooted inter-site mail flow before.  

Any ideas?

Jason
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Question by:trivalent
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Expert Comment

by:rakeshmiglani
ID: 16597369
is message tracking enabled? what does it tell you?

in which queues are the messages stuck?

any smart host entry on the new server?
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Accepted Solution

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brakk0 earned 750 total points
ID: 16598009
Are the servers in the same routing group? Have you set up routing groups?  Since it is temporary, you could try configuring two routing groups, put one server in each group and configure routing group connectors to move the mail.
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by:trivalent
ID: 16598645
>Is message tracking enabled? what does it tell you?

I've turned on message tracking - but I'm not sure what I'm learning.  What extended properties should I enable?

>in which queues are the messages stuck?  

The messages are stuck in the queue for (new exchange server name).(domainname).local under the old Exchange server

>any smart host entry on the new server?

No there is not.

The old Exchange server has not been put up to SP2 yet.  Do you think that would make a difference in this scenario?
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LVL 35

Expert Comment

by:rakeshmiglani
ID: 16598692
try doing a telnet on port 25 on the exchange servers to check whether you are able to drop an email via telnet

XFOR: Telnet to Port 25 to Test SMTP Communication
http://support.microsoft.com/kb/153119/en-us
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Author Comment

by:trivalent
ID: 16598748
> try doing a telnet on port 25 on the exchange servers to check whether you are able to drop an email via telnet

Done that.  Success both ways.
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Expert Comment

by:rakeshmiglani
ID: 16598801
if you double click on any message stuck in the queue, do you see any information there.
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Author Comment

by:trivalent
ID: 16599103
> if you double click on any message stuck in the queue, do you see any information there.

Yes, in the message properties it seems to be in a permanent 'Retry' state.   I've tried forcing the connection...
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LVL 35

Expert Comment

by:rakeshmiglani
ID: 16603488
Cannot think of anything else.. try installing and running the following MS tool and see if it tells you anything

Microsoft Exchange Server Best Practices Analyzer Tool v2.6
http://www.microsoft.com/downloads/details.aspx?familyid=DBAB201F-4BEE-4943-AC22-E2DDBD258DF3&displaylang=en
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