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Migrating to Exchange 2016 from Exchange 2010

Posted on 2016-08-19
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Last Modified: 2016-08-29
I am having trouble with my migration from 2010 to 2016.  I've made a lot of progress, I have the old 2010 server with all the mailboxes running and the new 2016 server handling all the ActiveSync and OWA requests via proxy.  It works fine, no issues.  The existing local outlook users using OL2010 and higher are connected without a problem.  I migrated one mailbox as a test and that client is not able to connect, it asks for the users password every time they open outlook, but when they type it in it doesn't work, just pops right back again and again and never connects to the server.  That same users mobile devices and also OWA work just fine no issues,  it is on local outlook that doesn't work. I have been searching all day and have no solutions so I'm hoping someone out there has had this problem and has a solution, I have looked through the logs and am not able to find anything useful.  I'm not an exchange expert but I have been managing this server for years and need help please.
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Question by:WhittonPlumbing
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by:-MAS
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Did you configure your outlookanywhere?
https://technet.microsoft.com/en-us/library/bb123545(v=exchg.160).aspx
Did you point your common name to Exchange2016? For testing you can add a host record in a PC which points to Exchange2016 and check outlook.
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by:Jeffrey Kane - TechSoEasy
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Did you try creating a new Outlook profile for this user?
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by:WhittonPlumbing
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I've created a new mailbox on the Exchange 2016 machine and created a brand new user profile and outlook profile and I have the same result.  

I ended up migrating the test mailbox back to Exchange 2010 and it is working now, but of course this is not the desired end case.  

I have also verified that Outlook Anywhere is running on both the Exchange 2010 and Exchange 2016 setups with NTLM. I have my DNS pointing the host name for mail.mydomain.com to the Exchange 2016 server and that is what is published in the Outlook Anywhere for Internal and and external host name.  

I also have pointed all my URLs (virtual directories) to this host name for the new server.

Is there any log or test procedure that I can get more information about the failure or I could post that would be helpful in solving this.
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by:WhittonPlumbing
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Ok, so it turns out that other users work fine, I have tested two or three, but my user account won't work.  Running the Microsoft Remote Connectivity Analyzer for both autodiscover and connectivity for outlook return success, but on my machine and on another clean machine it doesn't work, autodiscover is failing.  That same clean machine I have tested creating a profile for the other users and they work fine.  I have also pursued the AutoMapping potential issue and that doesn't seem to be it since I removed all the delegated boxes from my account and still had the same problem.  The log from the outlook Test Email AutoConfiguration tool states simply that autoconfiuguration was unable to determine your settings!  The log tab has several attempts to connect to https://mail.company.com/autodiscover/autodiscover.xml that fail with httpStatus 302 (a redirect) and error 0x800C8204, and 0x800C8203.  I hesitate to migrate an other critical users over to the new server until I have a solution to this, I can live without outlook, not fun but I can do it while I figure this out, but I'm not about to try it on others unless they only use mobile devices and OWA which I know works.

Any other help please?
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WhittonPlumbing earned 0 total points
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So, issue is resolved!!  After migrating several other users with success I decided to restart the server again and everything started working again.  Must have been an issue with a stuck connection or something to my mailbox.  That is usually the first thing I do is reboot with issues like this, but didn't think it was an issue since other users had migrated without an issue and without reboot. Dumb mistake.  In the end the only issue was that MAPI virtual directories didn't have the correct authentication flags set. No idea why they weren't set by default, but none of them were set, once I did that and then migrated several successful mailboxes and then rebooted the server, all is well.
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by:WhittonPlumbing
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Discovered problem on my own
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