Using Classic Outlook on Windows for personal email, calendar, and contact management
hi,
The repeated pop-up asking for your username and password means an app or service like Outlook, OneDrive, or a network share is failing to authenticate. This usually happens because saved credentials are outdated or incorrect, or network settings VPN/proxy interfere with login.
To fix it:
Identify which app or server is requesting credentials.
Update your username and password in that app.
Clear old credentials from Windows Credential Manager or macOS Keychain.
Check VPN/proxy settings and ensure the server address is correct.
Happy to help!