I have a multi-tennant, Exchange 2007 environment that I am trying to migrate to Exchange 2013. I think I'm ready to swing the DNS over, for co-existence, but want to test first. I have updated my Hosts file, and am seeing odd behavior in my tests. I wonder if my test is flawed, or if there is a misconfiguration somewhere in my Exchange 2013 environment.

The following IPs modified, but are correctly related to each other and I'm sure they are all able to communicate with each other. Here is what I have :

+ 2007 
- CAS/HT = 10.x.x.2/200.x.x.2

+ 2013
- Load balancer = 10.x.x.3/200.x.x.3
- CAS-MBX1 = 10.x.x.4
- CAS-MBX2 = 10.x.x.5
- CAS-MBX3 = 10.x.x.6

+ Hosts file
200.x.x.3 webmail.hosteddomain.com autodiscover.hostedserver.com autodiscover.customer1.com autodiscover.customer2.com
200.x.x.2 legacy.hosteddomain.com

The test mailbox for Customer 1 is on Exchange 2007 and the test mailbox for Customer 2 is on Exchange 2013. 

Here are my tests, and their results:

+ Test 1
1. webmail.hosteddomain.com -> enter Customer 1 credentials -> browser shows "Redirect loop detected" or "The website declined to show this webpage (http 403)"

+ Test 2 
1. Log into Windows with Customer 1 credentials -> open Outlook -> name detected -> "Your account was redirected to https://autodiscover.hosteddomain.com/autodiscover/autodiscover.xml" -> Allow -> mailbox displayed

+ Test 3
1. webmail.hostedserver.com -> enter Customer 2 credentials -> mailbox displayed

+ Test 4
1. Log into Windows with Customer 2 credentials -> open Outlook -> name detected -> "You must restart Outlook for these changes to take effect" -> OK -> without restarting Outlook, "Outlook cannot log on. Verify you care connected to the network and are using the proper server and mailbox name." -> OK -> Microsoft Exchange server: CAS-MBX3, Mailbox: Test User -> check name -> "Outlook cannot log on. Verify you care connected to the network and are using the proper server and mailbox name." -> OK -> "The name cannot be resolved. The action cannot be completed."
2. Change Microsoft Exchange server to serverGuid@customer2.com -> check name -> "Outlook cannot log on. Verify you care connected to the network and are using the proper server and mailbox name." -> OK -> "The name cannot be resolved. The action cannot be completed."
3. Open Hosts file and change webmail.hosteddomain.com to 10.x.x.3 -> check name -> "Outlook cannot log on. Verify you care connected to the network and are using the proper server and mailbox name." -> OK -> "The name cannot be resolved. The action cannot be completed."

So my Exchange 2007 user cannot log into OWA and my Exchange 2013 user cannot use Outlook. What am I missing here?

Thanks.

• Edited by mhashemi 14 hours 57 minutes ago fixed a typo

Hi,

Thank you for your question.

For Exchange 2007, we should change internal URL to https://legacy.domain.com

1.        OWA: https://legacy.domain.com/owa
2.        EWS: https://legacy.domain.com/ews/exchange.asmx
3.        Autodiscover: https://autodiscover.domain.com/Autodiscover/Autodiscover.xml

Use the following command: Eg;

OWA:

Set-OwaVirtualDirectory Identity ex2013\owa (Default Web Site) InternalUrl https://webmail.domain.com/owa ExternalURL https://webmail.domain.com/owa

Set-OwaVirtualDirectory Identity ex2007\owa (Default Web Site) InternalUrl https://legacy.domain.com/owa ExternalURL https://legacy.domain.com/owa

Outlook Anywhere:

Set-OutlookAnywhere Identity Ex2013\Rpc (Default Web Site) InternalHostname webmail.domain.com ExternalHostName webmail.domain.com ExternalClientAuthenticationMethod Basic IISAuthenticationMethods Basic,NTLM

Set-OutlookAnywhere Identity Ex2007\Rpc (Default Web Site)  IISAuthenticationMethods Basic,NTLM

EWS:

Set-WebServicesVirtualDirectory Identity Ex2013\EWS (Default Web Site) InternalURL https://webmail.domain.com/EWS/Exchange.asmx ExternalURL https://webmail.domain.com/EWS/Exchange.asmx

Set-WebServicesVirtualDirectory Identity Ex2007\EWS (Default Web Site) InternalURL https://legacy.domain.com/EWS/Exchange.asmx ExternalURL https://legacy.domain.com/EWS/Exchange.asmx

Autodiscover:

Set-ClientAccessServer Identity Ex2013 AutoDiscoverServiceInternalUri https://autodiscover.domain.com/Autodiscover/Autodiscover.xml

Then we should have the following record in DNS:

legacy.domain.com                  10.x.x.2

webmail.domain.com              10.x.x.3

autodiscover.domain.com     10.x.x.3

If there are any questions regarding this issue, please be free to let me know.

Best Regard,

Jim

Right, but I can't change the production environment, until I have tested. How do I test without impacting prod?

• Edited by mhashemi 5 hours 5 minutes ago