This article to guide on how to solve Outlook keep prompt window to ask for enter password:
1. Reboot the computer.
2. Check your internet connection to make sure do not have internet connection interruption.
3. Make sure that the “remember password” option is selected for that account.
4. Check your antivirus software and try to temporary disable the antivirus.
5. Check the correct user credentials are stored on your computer.
6. Disable shared calendars to see if that is causing the problem
If you have done above troubleshooting steps but the issue persist, you are advice to reset your email account password in your control panel and update the new password in your Outlook.
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