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Mail does not flow from Exchange 2010 to Exchange 2003- Error 421 4.2.2 Socket Error

Posted on 2010-11-18
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Last Modified: 2012-05-10
I am unable to route email from an Exchange 2010 box to my Exchange 2003 server.  Messages sit in the queue on the 2010 server, and I finally get an error 421 4.2.2 and something about a Socket error.  I have not been able to get the exact message because it only appears when the queue goes into Retry mode (as opposed to Active) which is not very often.  Users on the Exchange 2003 server can send to a user on Exchange 2010.  Everyone can send and receive Internet email (Exchange 2003 is receiving inbound SMTP).  The issue is strictly one way from Exchange 2010 to Exchange 2003.

I worked with Microsoft Tech support yesterday, but they have not been able to solve.  I am waiting for a call back from their Level 2 support.

More details:
-Exchange 2010 running on Windows 2008 R2 configured as DC
-Exchange 2003 running Windows 2003 R2, configured as DC
-There are two other Exchange 2003 servers in the organization, not being used, will be retired


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Question by:stschoppe
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by:EndureKona
ID: 34165617
Not sure what help this will be since I believe MS support would cover all this what I would do.

Have you recreated the Routing Group Connector between Exchange 2003 and Exchange 2010?   Delete the current connectors and create a new one.

New-RoutingGroupConnector -Name “Interop Exchange 2003” -SourceTransportServers “exchange2003.localdomain.local” -TargetTransportServers “exchange2010.localdomain.local” -Cost 1 -Bidirectional $true -PublicFolderReferralsEnabled $true

If this does not work run Exchange BPA for both servers and look for any type of security permission issues.   I have seen a lot where permissions are changed and don't inheret
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stschoppe earned 0 total points
ID: 34167488
The issue was resolved by unloading the Trend Micro client from the computer.  I had removed the Trend Messaging Agents early on in the troubleshooting process.  However, I did not realize that a Trend Agent was installed.

Glad it was an easy fix, but I wish I would have figured it out 24 hours ago.
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by:Alan Hardisty
ID: 34869529
This question has been classified as abandoned and is being closed as part of the Cleanup Program. See my comment at the end of the question for more details.
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Expert Comment

by:frank1976
ID: 35151525
I ran into this error after our firewall was updated. The issue for us was ESMTP inpsection by the f/w. Once we turned ESMTP inspection off the quques dumped out all the mail.
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Expert Comment

by:Alan Hardisty
ID: 35151849
Cisco firewall by any chance?
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Expert Comment

by:frank1976
ID: 35151895
Yes! why do u ask?
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by:Alan Hardisty
ID: 35151956
It's typical for a Cisco device and it messes up the flow of Exchange communications.

It will cause you sending mail problems (with it enabled) and it actually causes more problems that it solves!  A great feature (I think not)!

It basically restricts the SMTP Verbs being used and also disguises the FQDN of the server, so that other servers see your server as:

220 **********************************************************************

Which makes it very tricky for the receiving server to check the FQDN which it would normally be sending to verify the server is a valid mail server.

This, however, is not related to the above problem in the question - that is a separate issue as the mail-flow is internal not external.
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