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Exchange 2010 Routing Group Connector

I've just installed Exchange 2010 SP1 on a new server, in a domain that already has an Exchange 2003 Server.  I followed the steps in Technet on how to accomplish this, and seemingly all went well.  These are the only two exchange servers in the domain.

I moved one test user/mailbox from 2003 to 2010.  Everything I've tested works, except if I email the test user from an account associated with the exchange 2003 server.  Then the email ends up being queued in the "messages with an unreachable destination" queue

I've enabled diagnostic logging for MSExchangeTransport on the 2003 server and got the following error

MSExchangeTransport / Connection Manager / EventID 4006

Message delivery to the host '192.168.0.2' failed while delivering to the remote domain  '_4886135a22abb944886470d7c12473c7_D' for the following reason: The remote SMTP service rejected AUTH negotiation.

Where 192.168.0.2 is the IP of the 2010 Exchange Server

I'm relying on the "routing group connector" created during the install for the communication from 2003 to 2010.

I understand what this error is, but in the context of the "routing group connector" I've no idea how to proceed to resolve what it really means and fix it.

Any and all advice appreciated.

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cteakle
Asked:
cteakle
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2 Solutions
 
Glen KnightCommented:
There are a number of issues that can cause this, first thing to do is check my guide here: http://www.experts-exchange.com/Software/Server_Software/Email_Servers/Exchange/A_3044-Exchange-Server-Mail-Flow.html

Then check the check boxes on the permissions tab of the default receive connector on the Exchange Server.
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Muzafar MominCommented:
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cteakleAuthor Commented:
DEMAZTER:  I checked as you suggested and neither problem1 nor problem2 are applicable

MUZAFAR13:  I created an additional routing group connector as suggested.  on exchange 2003 all messages the "messages with an unreachable destination queue" were re-queued to the newly created queue, however before long all appeared back on the "messages with an unreachable destination queue"

The same error, eventid 4006 appeared in the application log.

I fear that the newly created connector has the same issue as the one created during the install

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Glen KnightCommented:
Can you telnet from the 2003 server to the 2008 one on port 25?

Have you disabled IPv6? if so, re-enable it.
Have you by anychance installed the SMTP component on the 2008 server? if so remove it as it's not required for Exchange 2010
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cteakleAuthor Commented:
yes I am able to telnet on port 25.   if I point outlook to use the 2010 server as my smtp server, I can happily send all the mail I want.   I've not used telnet on port 25 to send mail

I've not touched ipv6

no, I've not installed smtp component

it seems that the problem boils down to either
1. why does 2003 server want to use AUTH to communicate
or
2. why does 2010 server not want to use AUTH to communicate
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Glen KnightCommented:
can you post a screenshot of the last 2 tabs on the Default Receive connector on Exchange 2010 please?
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cteakleAuthor Commented:
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Glen KnightCommented:
That's fine, you must be using some sort of authentication on your Default SMTP Virtual Server.
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cteakleAuthor Commented:
on 2003 Default Virtual Server has

 screensot form 2003 server
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Glen KnightCommented:
Can you actually do a telnet test to send an email via telnet from the 2003 server to the 2010 server as per: http://support.microsoft.com/kb/153119

Use valid email addresses.
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cteakleAuthor Commented:
I followed this methodology

email was successfully sent

email was also received successfully

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Glen KnightCommented:
So it's definitely a configuration of the Default SMTP Virtual Server.

I don't have any 2003 servers left to check on, but try stopping the current Virtual Server and creating a new Virtual SMTP Server.
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cteakleAuthor Commented:
I made the suggested change it made no difference

The message was still rejected due to same error by the 2010 server
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cteakleAuthor Commented:
Interestingly the two routing group connector I now have between the two exchange servers are how as DOWN from the 2003->2010 direction and as up in the 2010->2003 direction.

this is as seen from Tools -> Monitoring and Status -> Stats on the 2003 mgmt console

if I enable message tracking the message is successfully queued for remote delivery, but then ends up in the unreachable destination queue.

Soemthing has to be worng on the exchg 2010 side of thinsg ...
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Glen KnightCommented:
Delete both Routing Group Connectors that you can see in the Exchange System Manager.

Then in the Exchange Management shell run the following command:

New-RoutingGroupConnector -Name "Exch2010-Legacy" -SourceTransportServers "exchange2010.domainname.local" -TargetTransportServers "exchange2003.domainname.local" -Cost 1 -Bidirectional $true

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cteakleAuthor Commented:

I deleted both using EMS on the 2010 side of things.  both duly disappear on ExchgSysMgr on 2003

then new routing group connector was created

unfortunately same problem, I could see the messages requed to the new connector, then all moved to the unreachable

same error in application log file

same status for connector up from 2010->2003, down from 2003->2010

we still have to ask, why does 2010 reject the neogtiation ?
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Glen KnightCommented:
Can you check the SMTP Settings as per this article: http://support.microsoft.com/kb/329636
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cteakleAuthor Commented:
integrated windows authentication was set as delivery.outbound security

I reset to Anonymous

rebooted 2010 server

all the messages queued for the 2010 server disappeared from the unreachable queue, application log showed no errors

all messages have been delivered to my test account mailbox on the 2010 server

I've just re-read your original post, and the article it referred to.  you were on the right tack

a millions thanks for sorting this

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cteakleAuthor Commented:
awesome outcome
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