Outlook Keeps Prompting for a Password (Even with an App Password)

You know the thing. It usually manifests itself on AzureAD joined PCs. But, it keeps giving you that annoying prompt with the username but doesn't go away. Well boy howdy, here's a fix that made my day!

HKEY_CURRENT_USER\Software\Microsoft\Exchange

Add the DWORD AlwaysUseMSOAuthForAutoDiscover and set it to 1

HKEY_CURRENT_USER\Software\Microsoft\Exchange

Add a DWORD MsoAuthDisabled and set that angry dude to 1

HKEY_CURRENT_USER\Software\Microsoft\Exchange

Add a DWORD MapiHttpDisabled, set it to 0

HKEY_CURRENT_USER\SOFTWARE\Policies\Microsoft\Office\16.0\Outlook\AutoDiscover

Add a magical DWORD called ExcludeExplicitO365Endpoint

Set that thing to 1

Log out and back in (or rebootz if you're lazy restart-computer -force )

Profit.