Using Classic Outlook on Windows for personal email, calendar, and contact management
I've suffered the same problems for months with Outlook 2013 and just today found this resolution - No more prompts for password.
- Remove cached credentials
- Close all Microsoft Office Programs
- Navigate to Control Panel
- In the search bar, type in “Credential Manager” and select it
- Select Windows Credentials
- Under Generic Credentials select the down arrow next to any instance of MicrosoftOffice15_Data:orgid:*your email address* and remove it If you are using Office 365, it may say Office 365 instead of Office15.
- Open Outlook and input your new credentials when prompted. Make sure you check the box to remember your credentials.