Hi Tim, I understand how discouraging it must feel to keep entering the correct password only to see Outlook reject it, especially since you can log in just fine on the web it’s frustrating to be stuck in that loop.
To fix Outlook login failures clear stored credentials in Windows Credential Manager and restart Outlook, re‑add the account using Exchange or Office 365 with modern authentication repair or recreate your Outlook profile through Control Panel if needed generate and use an app password if two factor authentication is enabled update Outlook to the latest version and if problems persist, test in Safe Mode, check your network or firewall settings, and use the Microsoft Support and Recovery Assistant to automatically detect and resolve issues.
When you enter your password in Outlook and the login fails, do you see a specific error code or message on the screen or does it only say that the password is incorrect?
Best regards
Lucky Charm