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OWA for Exchange 2003 and 2010 during migration

Posted on 2014-02-24
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Last Modified: 2014-03-17
We are migrating from Exchange 2003 to 2010, then possibly on to 2013. For now I have a Exchange 2010 with all the roles on one server running on Server 2012 Hyper-V and have moved a couple test users over. Email comes and goes to them without issue.

However, I am not sure how to set up OWA for both systems. We have been using OWA for Exchange 2003 but something I did setting up 2010 seems to have redirected that. Anytime I go to the external URL we used to get to OWA on Exchange 2003 it rolls that test user over to the URL for the 2010 server, even tho Outlook Anywhere is not enabled yet on it.

What did I screw up and can I have both running at the same time?
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Question by:LarryDAH
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Expert Comment

by:Recept
ID: 39884065
That is the expected behavior, when you move users to the Exchange 2010 mailbox server they will be redirected to the 2010 OWA page.

It is best practice to get your Exchange 2010 CAS role built and configured, redirect all incoming OWA/ActiveSync traffic to that and then move mailboxes in behind it.
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Author Comment

by:LarryDAH
ID: 39884095
Hmm, well that is a bit of a problem. We are also evaluating Gmail and I wanted to have some test users on Exchange 2010 with Outlook 2010 to see how well it works and to compare the 2 email systems.

Does that mean that any user who could use OWA to get to the Exchange 2003 box is stuck unless I move them over to the 2010 box?
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Recept earned 250 total points
ID: 39884175
If you're only in testing you could configure and publish the Exchange 2010 under a different internet address - webmail2010.company.com for example however the users with the Exchange 2010 mailbox will always be redirected to the new OWA interface.

webmail.company.com -> Exchange 2003 OWA -> Exchange 2003 Mailbox
webmail2010.company.com -> Exchange 2010 OWA -> Exchange 2010 Mailbox
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Assisted Solution

by:Simon Butler (Sembee)
Simon Butler (Sembee) earned 250 total points
ID: 39884243
Exchange 2010 and 2003 can co-exist for OWA access, but only if you have two external IP addresses. Exchange 2010 cannot proxy to 2003 OWA, it will only redirect. You need to configure a legacy URL for OWA access.

This TechNet article explains how to migrate the client access functionality of Exchange 2003 to 2010, including the use of legacy URLs.
http://technet.microsoft.com/en-us/library/ee332348(v=exchg.141).aspx

Remember Exchange will happily downgrade, so redirect a user from Exchange 2010 to 2003, but very well the other way.

Simon.
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Author Comment

by:LarryDAH
ID: 39889314
Now something is broken. Not sure if I should start new thread.

I have a number of messages stacking up in the outbound queue. The last error is "451.4.4.0 Primary target IP address responded with '421.4.2.1 Unable to connect. Attempted failover to alternate host, but that did not succeed. Either there are no alternate hosts or deliver failed to all alternate hosts.

I still have my Exchange 2003 server running and have moved half a dozen users over to the new 2010 server. The odd thing is that most of the hung emails are from users that are still on Exchange 2003. Why are their emails being routed thru the new 2010 server?

I have used the Remote Connectivity Analyzer to test Exchange outbound smtp mail flow and it passed. The only issue was it did not find SPF record using DNS text record query.

However, the inbound test failed. All is green till it got to the 'Attempting to send a test email message to myemailaddress.org using MX mail.ourdomain.org.

Additional details:
The server returned status code 400 - Syntax error, command unrecognized. The server response was: defer
Exception details:
Message: Syntax error, command unrecognized. The server response was: defer
Type: System.Net.Mail.SmtpException
Stack trace:
 at System.Net.Mail.DataStopCommand.CheckResponse(SmtpStatusCode statusCode, String serverResponse)
 at System.Net.Mail.DataStopCommand.Send(SmtpConnection conn)
 at System.Net.Mail.SmtpClient.Send(MailMessage message)
 at Microsoft.Exchange.Tools.ExRca.Tests.SmtpMessageTest.PerformTestReally()
Elapsed Time: 61479 ms.
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Author Comment

by:LarryDAH
ID: 39889773
Found my second problem, my firewall had a rule limiting email to the IP of my Exchange 2003 box, I had to add the IP of the new box now mail is flowing out.
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