18 Oct 2011

Exchange 2010 mailboxes can not send to 2003 mailboxes

PROBLEM
Now we installed a new Exchange 2010 server in the same domain as the exchange 2003 server and installed the CAS, Mailbox and Hub roles. Next we about to move 70 mailboxes to the new Exchange 2010 server. Everything looks fine, users with mailboxed on the Exchange 2003 server can send mail to users on Exchange 2010 server. But the users with mailboxes on Exchange 2010 server can't send mail to mailboxes on exchange 2003. These messages stay in the 'SmtpRelayToTiRg' queue with error : 451 4.4.0 Primary Target IP address responded with: "451 5.7.3 Cannot Achieve Exchange Server authentication" 
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SOLUTION 1
I installed a Windows 2007 Exchange server in to my 2003 environment this week. All went well apart from that the mail sending from the 2007 test mailboxes ended up in a queue called smtprelaytotirg. The error message given being 451 4.4.0 Primary Target IP Address Responded with (501 5.5.4 Auth Command Cancelled).
This queue is basically where 2007 is failing to deliver because it can’t route correctly.
The resolution in this case for me was easy. All the connectors were in place as they should be, but the transport for SMTP on the original master 2003 Exchange server had limited access to certain IP addresses.
I added the IP address for the new Exchange 2007 server and bang, 20 mins later the queue is empty.
Just a minor hurdle :) Oh, the other one to watch out for is making sure it can resolve either by IP or FQDN for the SMTP server, it’ll fail on netbios or just a single name. Anyone still relying on WINS needs shot in the face with a screw driver.
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SOLUTION 2
http://forums.microsoft.com/TechNet/ShowPost.aspx?PostID=1087732&SiteID=17

Integrated Windows Authentication was not turned on, on my Default SMTP Virtual Server.....WORKED FOR ME

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