troubleshooting Question

Outlook 2010 prompts for password on existing profile when migrating from Exchange 2010 to 2016

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diperspFlag for United States of America asked on
ExchangeOutlook
5 Comments1 Solution3288 ViewsLast Modified:
We're in the process of testing our new Exchange 2016 server.  Very basic, no DAGs, single server, etc.  We're actually migrating from SBS 2011 (Exchange 2010.)

Mail flow is good, everything is working well, except when we move a mailbox to 2016.  Once it's moved, the user is prompted for a password and can not access their Outlook profile no matter what.  If we build a new profile for this user, then it works fine.  This is for any mailbox we move for testing.

I've been through the following tips/tricks -

- Installed the latest hotfixes for Outlook 2010 to handle internal/external namespaces for Outlook Anywhere and TCP over HTTPS.
- Enabled kernel mode authentication for EWS and autodiscover.
- Changed the default app pool to run against network services.
- Adjusted authentication on both Exchange 2010 and 2016 for NTLM against Autodiscover and EWS in IIS and against "get-outlookanywhere".  
- Loopback check for autodiscover was already disabled.  
- Microsoft Remote Analyzer shows no errors.
- Set-OrganizationConfig -MapiHttpEnabled $false (Tried this, set it back to true later.)

https://localhost/Autodiscover/Autodiscover.xml works fine.  
https://mail.domain.com/Autodiscover/Autodiscover.xml prompts for credentials

Again, the issue is ONLY when we move mailboxes.  I'd rather not recreate profiles on each machine in Outlook but this does work.
ASKER CERTIFIED SOLUTION
Ivan
System Engineer

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