Exchange 2010 - problem sending mail from one server

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Vespa Alex

We currently have two Exchange 2003 Standard Edition servers - one at Site A (local office) and one at Site C (remote office)
- and we are in the process of upgrading to Exchange 2010.
We have a total of three new Servers (all of which are running as Virtual Machines).
Exchange2010A is a Mailbox, Hub Transport and Client Access server at Site A (local office)
Exchange2010B is a Mailbox, Hub Transport and Client Access server at Site B (local datacentre)
Exchange2010C is a Hub Transport and Client Access server also at Site B
The plan is to migrate user mailboxes from both our old servers onto the new ones and then have a replicated copy of the databases in case our building burns down.
We have set up appropriate connectors to link the old and new halves of the organisation and created a Mailbox Database on 2010A. A test user has been created on this server and I can send and receive mail between them and an existing mailbox on both of our old servers, plus an external recipient.
I've then set up a DAG and created a replica of the database on the 2010B server and this worked ok - I can manually move the active database copy to the other machine for a controlled swap, and if one machine is shut down then the other assumes the master role.
The problem is that when the database is on the 2010B server, although users can connect ok via OWA or Outlook 2010, any messages that they send aren't delivered and eventually time out. As far as I can see, the two servers are configured the same, but clearly something is different.
<edit - fixed a problem with the ECP>

I've looked at one of the failed messages and I can see " '451 4.4.0 Primary target IP address responded with: " 451 5.7.3 Cannot achieve Exchange Server authentication." Attempted failover to alternate host, but that did not succeed. Either there are no alternate hosts, or delivery failed to all alternate hosts"

Can someone help me find where I've gone wrong as I'm now going round in circles.


Gulab Mallah

Check the send connector and make sure that Anonymus permission is checked and restart MS Exchange Transport service.

Gulab | Skype: gulab.mallah

Vespa Alex

I've double checked that it's set to use anonymous rather than Exchange authentication , but still have the problem.

Novak Wu


Please delete RGC between Exchange 2003 and 2010 and recreate it using the New-Routinggroupconnector command:

New-RoutingGroupConnector -Name " 2010-2003" -SourceTransportServers "" -TargetTransportServers "" -Cost 1 -Bidirectional $false -PublicFolderReferralsEnabled $true


New-RoutingGroupConnector -Name " 2010-2003" -SourceTransportServers "" -TargetTransportServers "" -Cost 1 -Bidirectional $false -PublicFolderReferralsEnabled $true

Please check the results running below cmdlet:

Get-RoutingGroupConnector| FL

Please also assure the SMTP Virtual Server is listening on the 25 port, and the Basic Authentication and Integrated Windows Authentication are checked.

If the problem still appears, please run the exchange best practices analyzer on 2k10 to check the mail flow and run get-sendconnector |fl command in EMS, then post the information on the forum.




Vespa Alex


In the end this turned out to be a firewall problem rather than an Exchange one.

There is a Cisco ASA between the two servers and it was the inspect esmtp command in the config causing it. Removed this and it started working.

Novak Wu


Thank you for sharing the solution to us. This can help other forum users in future who has the same problem.



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