Fix “Outlook Continually Prompting for Password” Issue When Connecting to Office 365?

It can be quite frustrating to see your Outlook program continually prompting for your password when you are trying to connect to Office 365. This issue generally occurs when you are trying to create an Outlook Profile or setting up a connection with Microsoft Office 365 mailbox. A “Trying to connect….” message is displayed on your email client while you are continually prompted for credentials. And if you try to cancel the password prompts, you would receive the following error message:

“The connection to Microsoft Exchange is unavailable. Outlook must be online or connected to complete this action.”

The prime cause of this issue is the value of the Logon network security setting located on the Security tab of the Microsoft Exchange window is set to something other than Anonymous Authentication. If you are also facing the problem with your Outlook program, you can resolve it by following the instructions provided below.

Guide to Fix “Outlook Continually Prompting for Password” Issue

For Newer Version of Outlook

If you are an Office 365 user using a new version, experiencing the error (as mentioned above) when trying to connect to an Exchange Online Mailbox, you can troubleshoot the issue by using the “Outlook Keeps Asking for my Password” diagnostic tool available on the Microsoft website.

The diagnostic will help by performing automated checks and provide possible solutions to get rid of the detected issues. Well, in case you are trying to connect to an Exchange On-Premises mailbox and Outlook prompts for a password when Modern Authentication is enabled, you can follow the information provided below.

1. Exit from your Outlook Email program on your computer.
2. Next, you will need to go to the Registry Editor

 

On Windows 7: Click on the Start button located on the lower-left corner, enter regedit.exe in the Search field, and press Enter key on your keyboard.

 

On Windows 10, Windows 8, and Windows 8.1: Press Windows Key + R Key to get to the Run dialog box. Then, you will need to enter regedit.exe in the Search box and press the “Enter” key on your keyboard.

3. Then, you will need to locate and click on the following registry subkey in the Registry Editor section:

HKEY_CURRENT_USER\Software\Microsoft\Exchange

4. Now, go to the Edit menu > New and then click on the DWORD Value.
5. Then, you will need to enter AlwaysUseMSOAuthForAutoDiscover, and then press Enter key on your keyboard.
6. After that, you will need to right-click on the AlwaysUseMSOAuthForAutoDiscover and select the Modify
7. Finally, you will need to click on the OK button in the Value data box and exit Registry Editor.

For Affected Versions of Outlook

In case you are using an older version of Outlook, you can change the Logon network security setting to Anonymous Authentication to overcome this issue. Here are the steps to it:

1. Exit from your Outlook email program and go to the Control Panel section to perform one of the following:
   • On Windows 8: You will need to swipe in from the right-hand side to open the charms bar, then tap or click on the Search option. Enter the “control panel” in the provided search field. Alternatively, you can enter the “control panel” in the Start screen, and then you can tap or click on the Control Panel option appearing in the search results.
   • On Windows 10, Windows 8.1, or Windows 7: You will need to click Start, enter “control panel” in the search box, and then press Enter key on your keyboard.

• Once you are in the Control Panel, you will need to locate and double-click on the Mail option.
• Next, you will need to click on the Show Profiles option, choose your Outlook profile and then click on the Properties option.
• Then, you will need to click on the E-mail Accounts option.
• Next, you will need to select your email account and then click on the Change option.
• Once you are in the Change Account dialog box, you will need to click on the More Settings.
• Under the Microsoft Exchange dialog box, you will need to select the Security
• Then, under the Login network security list, you will need to select Anonymous Authentication option and then click on the OK
• After that, Click Next > Finish > Close on the Account Settings dialog box.
• Finally, you will need to Close the Mail Setup dialog box and then click on the OK option to exit the Mail control

And, this is how you can easily fix “Outlook continually prompting for password” issue when trying to connect to Office 365.