Outlook Clients continuously prompt for username and password - Exchange 2016 Migration

In a recent Exchange 2010 SP3 Update Rollup 18 to Exchange 2016 CU5 migration for a client, we had issues with some users prompting for username and password continuously after their mailbox was moved to Exchange 2016.

After looking into this further, I noticed the HTTP�1�1������ and OWA�1 were missing from the protocolSettings when comparing a problematic user to my lab.

 
The settings in protocolSettings are controlled by the user CASMailbox settings "Set-CASMailbox".  As you see this user has IMAP4 and POP3 disabled as it has a 0 on it.

We want HTTP and OWA enabled with a 1.

After adding the following to the users protocolSettings and performing an iisreset this resolved the issue for the users in question.

HTTP�1�1������
OWA�1

 
Hope this has been helpful.
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