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Exchange 2010 & 2003 interoperability

Posted on 2010-11-30
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I have moved two mailboxes from Exchange 2003 to 2010. These two mailboxes can send to eachother, but not to anyone still on the exchange 2003 server. The users on the 2003 server are able to send to these two mailboxes. These two mailboxes are able to send/receive email to/from external accounts. When i attempt to send via telnet from 2010 server to 2003 server, i get the following message: 501 5.5.4 Invalid Address
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Question by:mray77
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by:Jdtuck
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Looks to be an inheritance issue, try this:

To re-establish inheritance:

1. Open ASDIedit by adding the snap-in to a MMC (should be included on your 2008 server where Exchange 2010 is installed)

2. Navigate to Configuration > Services > Microsoft Exchange > Exchange Organization > Administrative Groups > First Administrative Group > Servers

3. In the right pane, right click on the CN=Server Name of your Exchange 2003 Server, select properties

4. Navigate to the Security tab, hit advanced toward the bottom.

5. Check the checkbox that reads “include inheritable permissions” toward the bottom of the dialogue box.
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by:mray77
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It was already checked. I unchecked, and rechecked - same result.
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by:Jdtuck
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If you run the Exchange Troubleshooting Tools what errors do you receive?
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by:Jdtuck
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Can you telnet to port 25 on the 2003 server from the 2010 server, if not it sounds like an iterop route might not be setup.
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by:mray77
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When running Exchange Remote Connectivity Analyzer (ERCA) i get the following:

      Performing Outbound SMTP Test
       The outbound SMTP test failed.
       
      Test Steps
       
      Attempting reverse DNS lookup for IP address xx.xxx.xxx.xx.
       Reverse DNS lookup failed.
       
      Additional Details
       IP address xx.xxx.xxx.xx doesn't have a PTR record in DNS.
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by:mray77
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Yes, i can successfully telnet to the 2003 server from the 2010 server. However, every address i put in for MAIL TO: shows INVALID ADDRESS. Even if i put in an external address that i can email.
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by:Jdtuck
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You should have a routing group connector, delete it and recreate it, it should have been created when Exchange was installed.
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by:Jdtuck
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From PS run this:  Get-RoutingGroupConnector | FL   There should be 2 groups so you know it is bidirectional, but still delete and recreate it.
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by:mray77
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RunspaceId                   : e79bd1bb-873f-4f33-8fd8-157ba650e10b
TargetRoutingGroup           : First Routing Group
Cost                         : 1
TargetTransportServers       : {FSMAIL}
ExchangeLegacyDN             : /o=Four Star Greenhouses/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Configura
                               tion/cn=Connections/cn=MAIL-FSMAIL
PublicFolderReferralsEnabled : True
SourceRoutingGroup           : Exchange Routing Group (DWBGZMFD01QNBJR)
SourceTransportServers       : {MAIL}
HomeMTA                      : Microsoft MTA
HomeMtaServerId              : MAIL
MaxMessageSize               : unlimited
AdminDisplayName             :
ExchangeVersion              : 0.1 (8.0.535.0)
Name                         : MAIL-FSMAIL
DistinguishedName            : CN=MAIL-FSMAIL,CN=Connections,CN=Exchange Routing Group (DWBGZMFD01QNBJR),CN=Routing Gro
                               ups,CN=Exchange Administrative Group (FYDIBOHF23SPDLT),CN=Administrative Groups,CN=Four
                               Star Greenhouses,CN=Microsoft Exchange,CN=Services,CN=Configuration,DC=fsdomain,DC=com
Identity                     : MAIL-FSMAIL
Guid                         : ae73df7e-9a63-4579-bbf9-60c7c10f48c0
ObjectCategory               : fsdomain.com/Configuration/Schema/ms-Exch-Routing-Group-Connector
ObjectClass                  : {top, msExchConnector, msExchRoutingGroupConnector}
WhenChanged                  : 11/16/2010 5:58:21 PM
WhenCreated                  : 11/16/2010 5:58:21 PM
WhenChangedUTC               : 11/16/2010 10:58:21 PM
WhenCreatedUTC               : 11/16/2010 10:58:21 PM
OrganizationId               :
OriginatingServer            : fsutility.fsdomain.com
IsValid                      : True

RunspaceId                   : e79bd1bb-873f-4f33-8fd8-157ba650e10b
TargetRoutingGroup           : Exchange Routing Group (DWBGZMFD01QNBJR)
Cost                         : 1
TargetTransportServers       : {MAIL}
ExchangeLegacyDN             : /o=Four Star Greenhouses/ou=FSDOMAIN/cn=Configuration/cn=Connections/cn=FSMAIL-MAIL
PublicFolderReferralsEnabled : True
SourceRoutingGroup           : First Routing Group
SourceTransportServers       : {FSMAIL}
HomeMTA                      : Microsoft MTA
HomeMtaServerId              : FSMAIL
MaxMessageSize               : unlimited
AdminDisplayName             :
ExchangeVersion              : 0.1 (8.0.535.0)
Name                         : FSMAIL-MAIL
DistinguishedName            : CN=FSMAIL-MAIL,CN=Connections,CN=First Routing Group,CN=Routing Groups,CN=FSDOMAIN,CN=Ad
                               ministrative Groups,CN=Four Star Greenhouses,CN=Microsoft Exchange,CN=Services,CN=Config
                               uration,DC=fsdomain,DC=com
Identity                     : FSMAIL-MAIL
Guid                         : 5a7664cf-88a8-4665-8877-de90df08e60f
ObjectCategory               : fsdomain.com/Configuration/Schema/ms-Exch-Routing-Group-Connector
ObjectClass                  : {top, msExchConnector, msExchRoutingGroupConnector}
WhenChanged                  : 11/16/2010 5:58:21 PM
WhenCreated                  : 11/16/2010 5:58:21 PM
WhenChangedUTC               : 11/16/2010 10:58:21 PM
WhenCreatedUTC               : 11/16/2010 10:58:21 PM
OrganizationId               :
OriginatingServer            : fsutility.fsdomain.com
IsValid                      : True


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by:mray77
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I'm not sure what you are suggesting i delete? Are you suggesting deleting the SMTP Connector
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by:mray77
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SEND connector on the Hub Transport?
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Jdtuck earned 500 total points
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Here is a perfect walkthrough for doing this on both the 2003 and 2010 servers, also same issue you are having.

http://social.technet.microsoft.com/Forums/en-US/exchangesvrtransport/thread/61521f42-d031-475d-abe1-35350dd01e23
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by:mray77
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I'm going to go through this now. I have two receive connectors for some reason. One is titled CLIENT, and the other DEFAULT. Suggestions? Should i delete one of these?
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by:Jdtuck
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On the default properties under Authentication tab make sure 'Exchange Server Authentication' is selected, not required on the Client Properties, and then under the Permissions Group for both of them you will want to have 'Anonymous users, Exchange Users, Exchange Servers, and Legacy Exchange Servers', Partners is not required for either.  Also do the ESM 2003 settings.
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by:mray77
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I'm stuck on the:

And Recreate Routing Group connector under E2K3 Administrative group for both ways.

I believe i need an update for my exchange 2003 system manager. Where can i get this?
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by:mray77
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I got ahead of myself. On the receiver connectors, i deleted the one titled "client" do i need to recreate that?
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by:Jdtuck
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Yes you need to recreate the client connector.
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by:mray77
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Mail is now flowing from the queue, and all i've really done is delete the two connectors and recreated the one on the 2003 server from exchange 2003 system manager. I have not been able to recreate the second connector under Exchange Administrative Group using the exchange 2003 system manager. Can this be recreated using Exchange 2010? I'm getting a message on 2003 about needing System Manager 8.0 or higher.
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by:Jdtuck
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So mail is now flowing between the servers?  That is an unusual error as there is no newer version of ESM, that would be Exchange 2007 which has no ESM but has EMC.  
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by:mray77
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Yes, it appears so. I have tested the mailboxes for send/receive from both 2003 and 2010. I'm concerned that when i eventually take the 2003 server offline, mail flow will cease. I still don't have that 2nd connector built and i'm not sure how to build it.
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by:Jdtuck
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OK, if you can still send/receive internally between the servers and receive from external senders to both servers then I would say not to worry to much about the 2003 connector.  However, you set it up the same as you setup the default connector.  In regards to moving everything over to the new server and shutting down the 2003 server is completely different as that will require you to test mail flow and also verify that the public folders have replicated to 2010.  But as long as you can send/receive openly internally and out and between the 2 servers that is a good start.
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by:Jdtuck
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And if you need it, here is a walkthrough for recreating the connector.

http://support.appriver.com/KB/a403/how-to-build-a-smtp-send-connector-with-exchange-2007.aspx
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by:mray77
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Actually, it is the RECEIVE connector that was deleted. There is a DEFAULT receive connector still there. I guess i will push ahead, and troubleshoot if there are issues after shutting down the 2003 server. Thanks for the help!
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