One common reason Outlook keeps prompting for a password—even when credentials are saved—is due to issues with the Windows Credential Manager or authentication settings. Here are a few steps you can try:
Clear Cached Credentials
- Open Control Panel > Credential Manager > Windows Credentials
- Look for any entries related to Outlook or Microsoft Office and remove them
- Restart Outlook and re-enter your credentials
- If you're using Office 365, make sure **Modern Authentication** is enabled. This can be managed via your organization's admin settings. **Check for Updates** - Ensure Outlook and Windows are fully updated. Sometimes, outdated software can cause authentication issues. **Create a New Profile** - Go to **Control Panel > Mail > Show Profiles** - Create a new profile and set it as default to see if the issue persists **Disable Always Prompt for Credentials** - In Outlook, go to **File > Account Settings > Account Settings** - Double-click your email account and make sure the option **“Always prompt for logon credentials”** is unchecked
- Look for any entries related to Outlook or Microsoft Office and remove them
If the issue continues, it might be worth checking with your IT team to see if there are any domain or policy-related restrictions.