While migrating users from their local exchange server, to Microsoft Office365, I had run into issues where Outlook would not find the Office365 account, but insisted on using the local exchange server, even when the email domain was not one in which the exchange server was _supposed_ to manage.
The solution was found in this article on AgileIT. I simply run the Exchange Server Management Shell command:
Set-ClientAccessServer -Identity “SERVERNAME” -AutoDiscoverServiceInternalUri $NULL
After which Outlook discovered the Office365 exchange server.
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