FAQ #24: MS Outlook 2019 + Continuous Password Prompts

Issue:

Outlook keeps prompting for a password

Possible Resolution:

Add this registry key

REGEDIT

HKEY_CURRENT_USER\Software\Microsoft\Office\16.0\Outlook\AutoDiscover

Create a DWORD named ExcludeExplicitO365Endpoint

Set value to 1

Restart Outlook

Reference: https://community.spiceworks.com/topic/2228146-outlook-2019-keeps-asking-for-password-and-tries-to-connect-to-the-internet