Outlook 2016 / 2019 Prompts for Password after initial setup and connection to On-Premise Exchange 2016 Server

I rebuilt my Windows 10 VM Image for XenDesktop and was testing it. I ran Outlook 2019, which configured successfully, opened my mailbox, etc. I logged off, did some tweaking to the image and logged in again.

When I launched Outlook it was prompting me for a password. [More]