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Cannot connect to Exchange 2016 from Outlook 2019

The owner of my company has his computer off our premise AD domain but connects to our network.  We have a premise Exchange 2016 server and are running Outlook 2019 Standard.  He has a domain account but logs in using his Microsoft Account.  About 2 weeks ago his account stopped working on his main office computer.  Said disconnected/offline.  Tried everything to get it back up.  Finally blew away the profile and tried to create a new one.

That's where the "fun" started.  When ever I try to recreate the profile I get "Cannot start Microsoft Outlook. Cannot open the Outlook window. The set of folders cannot be opened. You must connect to Microsoft Exchange with your current profile before you can synchronize your folders with your Outlook data file (.ost)."  I have searched and have not been able to locate a solution.  Please help!!

Thanks
Dave

Added - One interesting this is that the .ost gets created - C:\Users\owner.name\AppData\Local\Microsoft\Outlook but has no content.
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I think that may have gotten me close.  I need to reboot the server to confirm.  Will do so tonight and let you know.

Thanks
Dave