Using classic Outlook for Windows in business environments
Disable the Always prompt for login option: Open Outlook and navigate to File > Account Settings > Account Settings. Select your email account and click Change. Click More Settings, then navigate to the Security tab. Uncheck the box next to Always prompt for login credentials and click OK.
When you select change, there is not even a more settings option or a security tab, so maybe need to have this looked into the next update.
This is driving me made this issue, completely unusable software, and will not be renewing in January.
Microsoft - ever heard of the phrase 'If it's not broken - DON'T fix it!!!'