Troubleshooting: Exchange Hybrid
I recently set up a hybrid configuration between Exchange 2010 SP3 and Office 365 for a client. First let me just say this process is not nearly as easy as Microsoft makes it out to be. There are many steps involved. One issue I came across after the Exchange hybrid configuration was set up was when I migrated an account from the on premise server to the cloud mobile devices such as phones and IPads. The Outlook client did not automatically update to the new server name. Everything I read says this should happen and devices should auto configure. It just failed and would not connect to the new server. After many hours of research and talking to Microsoft to no avail, I finally find the solution on my own. Below is what I found, how I resolved it and how I tested it.
After reading dozens of articles I finally pieced together what the potential issue was. When I opened a browser and went to the OWA URL for the onsite Exchange server, then typed in the user name and password for a user that I had already moved over (in this case my test user), what I found was the URL that it was redirecting to was https://outlook.com/owa/companyname.com. Company name is your company name. You would think at first look this is correct, but what I found was the address was not the correct one. Since our external DNS points to this address and that is the correct address for the onsite Exchange server it did still redirect me to the Office 365 portal because of the Hybrid configuration setup. Even though this aspect of it did work, I wanted to change the URL to what it was supposed to be according to Microsoft.
To verify that the URL I was seeing was the one coming from the on premises Exchange server, I opened the Exchange Management Shell and ran the following command.
Get-OrganizationRelationship | fl name.targetowaurl
This returned the https://outlook.com/owa/companyname.com that was wrong. The same one that I saw in my above testing. I then wanted to change this to the correct URL so I ran the following command in the Exchange Shell.
Set-OrganizationRelationship “On Premises to Exchange Online Organization Relationship” -TargetOwaURL:https://outlook.com/owa/federateddomain
Federated domain is your company name used for your OWA URL. For example, mail.contoso.com, you would use contoso.com in place of federated domain.
Once this was changed I again went through the test above to make sure the correct address was now showing up when OWA redirected me.
I have been testing moving email accounts that were set up in Outlook, on an android Samsung S5, and on an IPad and they were failing, forcing me to delete the accounts and re-add them. Now that I had made this change I wanted to test again. I had an account in Office 365 and all three items (Outlook, phone, iPad) were all pointed there and working.
I migrated the account back to the on-premise server using the Office 365 portal. Once completed, none of the devices worked. This seemed correct to me since I had read it does NOT work when going from Office 365 to on-prem.
I started a migration back to Office 365. Once completed, I checked OWA and it redirected me correctly. I then looked at Outlook on my computer and it said “An Administrator had made a change and I needed to restart Outlook”. This was a good sign. I restarted Outlook. I again got the same message. I had read this would happen twice so I restarted Outlook for a second time and once it came back up it was working correctly.
Next I checked the IPad and Android phone. Both had worked correctly and automatically changed to the Office 365 server. I checked the server name on both and it was correct.
It appears the Target OWA URL was the issue. I hope this can help anyone else that has this issue.
In case you are curious the Target OWA URL is set when you go through the Hybrid Configuration Wizard. Sometimes it appears it just needs to be changed. As explained here.
The other two websites that lead me to my conclusion are:
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