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Outlook not connecting to mailbox after move to Exchange 2016

I am in the process of transitioning Exchange 2010 to Exchange 2016.  Have moved several mailboxes to Exchange 2016 that are being successfully accessed with Outlook and OWA.  However, there is one mailbox (we'll call the user John Doe) that was successfully moved and the mailbox is accessible via OWA but not accessible with Outlook.  Attempted to connect from several other workstations and Outlook clients but same result.  We move the mailbox back to Exchange 2010 and everything works without issue.

Then we exported the John Doe mailbox to PST, deleted it from Exchange 2010, created a new mailbox for John Doe in Exchange 2016, and imported PST.  Outlook is unable to connect to the mailbox on 2016.  If we move the mailbox back to Exchange 2010, Outlook is able to access the mailbox without issue.

It appears the auto-configutation is working properly as the user's mailbox info populates Outlook when the profile is being created.  We've even deleted the Windows profile from on of the workstations but made no difference.

Any thoughts that could guide me?

Thank you in advance.
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Todd Nelson
Asked:
Todd Nelson
3 Solutions
 
suriyaehnopCommented:
The user able to ping and nslookup autodiscover

Try use outlook to:

1. Test connectivity
2. Test e-mail configuration ( select autodiscover only)
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Todd NelsonSystems EngineerAuthor Commented:
Can ping and nslookup Autodiscover without issue.

ExRCA (testconnectivity.com) tests run successfully.

I'll try the Outlook testing options however they aren't available with the mailbox on the 2016 server.
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JagarmTechnical Support AnalystCommented:
Try Microsoft Office Configuration Analyzer Tool 2.2 and see if that finds any issues with the configuration

Also did you disable exchange cached mode in outlook and created new email profile?
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IvanSystem EngineerCommented:
Hi,

have you tried with restart of Autodiscover Application Pool? I hade the same problem with few users, that were migrated from 2010 to 2016, and that has helped.

There is MS KB on it.  https://support.microsoft.com/en-us/kb/3097392

Regards,
Ivan.
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Todd NelsonSystems EngineerAuthor Commented:
Unfortunately, for this specific user, the resolution was to delete the AD account and associated mailbox, and recreate them.

However, if the issue crops up again, I will try recycling the autodiscover app pool and use OffCAT.

Thanks.
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Todd NelsonSystems EngineerAuthor Commented:
Had the connectivity issue reoccur and recycled the app pool with success.

Thanks all.
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