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Avoid Outlook Constantly Prompting for Username and Password Issue


While making an Outlook account or synchronizing Outlook account with the MS Office 365, at some point the user may face an error Outlook constantly prompting for username and password. Almost all the case there occurs issue or error display like trying to connect. If the user try to halt the process or the credential prompt the error message will be shown like below:

Connection to Microsoft Exchange is unavailable.

Cause of Occurring Error

The cause of error will be arrived if there is any problem regarding with the Login Network Security Settings which is on Security tab of Microsoft Exchange Online. The pop-up box is set to specified value rather than Anonymous Authentication.

Why Does Outlook Constantly Prompting for Username and Password?

The cause of this error is due to various reason and the root cause is because of the following reasons mentioned below:

1. Outlook is configured to prompt for credentials.
2. While the wrong password is cached in the credential storage.
3. Authentication setting is necessary for an incoming and outgoing server.
4. Due to damaged profile, slow, unstable connection.
5. Due to installed anti-virus.

Resolution to Outlook Constantly Prompting for Username and Password Error

Microsoft Outlook latest version of Outlook is not affected by the credentials prompting issues. The latest Outlook edition has been removed the login Network Setting of Exchange account. If the user is using an Exchange Online Mailbox and updated the MS Outlook it is recommended to use the O 365 Support and Recovery Assistant to troubleshoot the Outlook connectivity for the recovery of Outlook Error.

Outlook Prompts for Password while Enabled Modern Authentication

For resolving the issue, go through the following scenario:
Scenario: Outlook account is connecting to Primary Mailbox in on-premises Exchange Server using RPC, and connects to other different Mailbox possessed in Exchange Online.

Resolution: In such cases, the Outlook constantly prompting for username and password and won’t make use of Modern Authentication to connect to Microsoft Exchange Online. Follow the steps mentioned below to resolve the error.

  • Quit MS Outlook, and start Register Editor. To do the whole process, follow the procedure for the desired edition of Windows OS.

For Windows 10/ 8.1/ 8: Press Windows Key+ R or the command prompt and open the dialog box. Enter regedit.exe in the Search box and select Enter. In the Registry Editor, find and hit the registry subkey:

  1.  HKEY_CURRENT_USER\Software\Microsoft\Exchange
  2.  From Edit menu, show to NEW, and select the DWORD value
    3. Enter the command AlwaysUseMSOAuthForAutoDiscover, and hit Enter
    4. Right Click on AlwaysUseMSOAuthForAutoDiscover, and select Modify
    5. Inside the value data box, type 1 and hit OK and Exit the Registry Editor

MS Outlook Prompting for Domain in Case Password Changes

While the domain user account changes then, in those case the MS Outlook 2013 prompt for the password. And if the password has changed, then type the new password and select or enable the remember the credentials.

Reason: The credentials are not getting overwritten before the password was changed and the credentials were saved. While that case the Outlook will pop-up a window then enable my credentials option. To resolve this install the latest updated Microsoft Outlook version.

If it is not working then follow the below-mentioned steps:

  1. Select the Start icon, Control Panel >> Credential Manager
    2. If view by is set to category, pick the Users Account >> Check Credential Manager
    3. Search and find outset of credentials including Outlook in name
    4. Hit on name and expand Set of Credentials >> Click Remove from Vault

Alternate Method: In certain case, the users will have the old version of their system. While that case if the user needs to fix the Outlook constantly prompting for username and password and also if needed to change the Login Network Security to Anonymous Authentication perform the below steps:

  1.  Quit MS Outlook and click and open Control Panel.
    2. Double-click Mail option.
    3. Hit on Show Profile and select the Outlook Profile >> Properties.
    4. Hit Email Account and click on Change option.
    5. In Change Account opt for More Settings and in Microsoft Exchange opt for Security tab in the dialog box.
    6. From Online Login Network Security list select Anonymous Authentication and hit on OK.
    7. Hit the Next option and then press Finish and select for close account settings in the dialog box.
    8. Then after, press Close on the Mail Setup dialog box and hit on OK.


The above article will show why and how the Outlook constantly prompting for username and password issue is fixed. It is discussed with the reason and solution so that the user will get a clear cut idea about this error.