Outbound mailflow problem after migrating mailbox to new Exchange 2013 Server

We just installed a new Exchange 2013 server and have coexistence with an existing Exchange 2010. Both are multi-role Mailbox/CAS. We are in the process of migrating completely to the 2013 server.
With user mailboxes residing on the 2010 server's database inbound and outbound mailflow is functioning properly to internal and external recipients, and is being proxied through the 2013 server.

When we move a mailbox to the 2013 server's database we are able to receive mail from internal and external users, but email sent from this mailbox is not received by external addresses.
There is only one send connector, and both the 2010 and 2013 servers are listed as source servers.
Delivery report shows: Submitted, Pending, Transferred, and "handed off to another email system".
There are no messages stuck in the queues on either server.
The test mailbox user does not receive a NDR or other bounceback
If we move the mailbox back to the 2010 database we can once again send mail externally.

What other troubleshooting steps can we take to determine the cause of this issue?
VerticalSolAsked:
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AmitIT ArchitectCommented:
Best way to troubleshoot this issue is to use telnet command. Try this article.

http://msexchangeguru.com/2013/08/03/e2013-2010mailflowissue/
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VerticalSolAuthor Commented:
Amit, Thank you for the suggestion. Following that article, below are the responses I received from each server.

Exchange 2010 server:
250-EXCH2010.domain.local Hello [My IP]
250-SIZE
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-STARTTLS
250-X-ANONYMOUSTLS
250-AUTH NTLM
250-X-EXPS GSSAPI NTLM
250-8BITMIME
250-BINARYMIME
250-CHUNKING
250-XEXCH50
250-XRDST
250 XSHADOW


2013 Server:
250-EXCH2013.domain.local Hello [My IP]
250-SIZE 37748736
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-STARTTLS
250-X-ANONYMOUSTLS
250-AUTH NTLM
250-X-EXPS GSSAPI NTLM
250-8BITMIME
250-BINARYMIME
250-CHUNKING
250 XRDST

Not sure how to use that information for troubleshooting. There are obvious entries missing from the new 2013 server when compared to the 2010: XSHADOW & XEXCH50.

Also, I don't know if it is significant, but I noticed that the exchange 2013 server does not show up under the 2010 EMC (under server configuration, running get-exchangeserver, etc.). The 2010 server does show 2 databases, including the database that resides on the 2013 server. I verified I can ping the 2013 server by Ip and hostname from the 2010 server. The exchange 2013 server displays both itself and the 2010.
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Justin YeungSenior Systems EngineerCommented:
Why don't try to create a new send connector and split Exchange 2010/2013 on 2 different connectors?

and it is normal that you can't see 2013 on 2010 environment.
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VerticalSolAuthor Commented:
Thanks Justin for confirming the 2010 EMC issue and for suggesting the new receive connector.

To answer your question: the migration steps we are following specify to add both 2010 and 2013 as source servers to the default send connector, and then remove the 2010 once mailflow is transferred to the 2013 server and 2010 server can be decommissioned.

Also, I previously tested telnet on port 25 from a local machine (results posted above) and it appears to be successful. When I try to telnet on port 25 from the 2010 server to the 2013 server I receive the following reply:
"421 4.3.2 Service not available"

I receive the same error trying to telnet in externally

I have tested this with windows firewall turned on and off, but I receive the same error either way.
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VerticalSolAuthor Commented:
Thank you both for the suggestions, we were able to resolve our issue. The telnet test put us on the right direction, but the test did not produce relevant results until we ran it from the exchange 2010 server and realized that it was not able to route mail to the 2013 server properly.

We also tried to create a new send connector, which did not solve the issue, however it did assist in the resolution. We reviewed our send and receive connectors on both servers and discovered the problem.

The problem was that we had limited the receive connector on the new 2013 exchange server to only accept mail from IP addresses of a spam filtering service. Once we modified the default frontend receive connector on the 2013 server to include the IP of the 2010 server all mailflow internal/external is now working. This was an oversight that only would have been a problem during the co-existence period. Thanks Amit and Justin for pointing us in the right directions to resolve this.
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AmitIT ArchitectCommented:
Great. Telnet is best tool for email troubleshooting. That's the first tool, I always use it. Then use Portquery tool. Then Netmon tool to trace the traffic. By using ping and tracert commands.
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