Hi @Keith Wong ,
There are several reasons why Outlook may be constantly prompting for a password, and you can try the following troubleshooting:
- Try clearing the Windows Credential Manager. This can be done by going to Control Panel > User Accounts > Credential Manager > Windows Credentials, then finding and deleting any credentials related to the account.
- Check if the Autodiscover settings are configured correctly for the Exchange account. Autodiscover is responsible for configuring Outlook to connect to the Exchange server. You can test Autodiscover by holding the CTRL key and right-clicking on the Outlook icon in the taskbar, then selecting "Test E-mail AutoConfiguration". Make sure that the Autodiscover results show the correct settings.
- Create a new profile from control panel: Go to Control Panel > Mail > Show Profiles, remove the old profile and click on "Add" to create a new profile. From there, manually add your email account and see if you can send or receive emails.
You can also refer to this article to troubleshooting: Outlook troubleshooting: Outlook keeps prompting for password.
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