Hi Ross Plowman
Thank you for reaching out in the Microsoft Q&A Forum. From your post, I understand you’re trying to look for solutions related to app password problems in Classic Outlook for Windows.
To help me guide you more specifically, could you please share a bit more information, such as:
- Are you using a personal Microsoft account (Outlook.com/Hotmail/Live/MSN), or a work/school account (managed by your company/school)?
- Are you using two‑step verification / MFA on that account?
- What exact message/error do you see?
- Can you sign in to the same mailbox successfully in a web browser?
In case Outlook keeps asking for a password, please try clearing old credentials:
- Close Outlook
- Open Control Panel > User Accounts > Credential Manager
- Under Windows Credentials, remove entries related to Outlook/Microsoft Account
- Reopen Outlook and sign in again
Looking forward to your reply so I can assist you further. I'm happy to help!
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