My Outlook keeps asking for password again and again, what should I do? If Outlook keeps asking for password repeatedly, first, check that your login credentials are correct and that your account is not locked. Next, go to the control panel and clear your cached credentials by selecting "Credential Manager." If this doesn't work, try disabling "Always prompt for logon credentials" in the Outlook settings. If the issue still persists, try repairing or reinstalling Office using the Control Panel. Visit: https://www.emailtechnicalsupport.us/blog/outlook-keeps-asking-for-password/