Outlook keeps asking for password when connecting to Office 365

If you’re seeing repeated prompts for a password when connecting to Microsoft 365 (formerly Office 365) on your Windows 10 device, then this post is intended to help you with the solution to resolve this issue. We will also identify the cause of this issue.

Let’s take a look at the typical scenario where you encounter this issue.

When you try to connect to a Microsoft Office 365 mailbox or create an Outlook profile, you might get prompted for credentials repeatedly, with the client saying ‘Trying to connect…’ each time. If you cancel the credentials prompt, you’ll get this error message:

In this case, the problem might happen if the Logon network security setting is set to something other than Anonymous Authentication on the Security tab of the Microsoft Exchange dialog box.

Outlook keeps asking for a password when connecting to Office 365

If you’re faced with this issue, you can follow the instructions below to resolve the issue.

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Versions of Outlook 2016 and Outlook 2013 that are not affected by this issue have the Logon network security setting disabled or removed from the Microsoft Exchange email account settings.

Microsoft’s Office 365 is a great productivity tool for users; however, some users may experience an issue where Outlook constantly prompts for a password. This can be fixed by running Microsoft’s Outlook Diagnostics tool. Simply open Microsoft’s Outlook Diagnostics tool and follow the on-screen instructions.

If you have an older version of Outlook, you need to set the Logon network security setting to Anonymous Authentication to fix this issue.

Do the following:

  • Exit Outlook.
  • Press the Windows key + R to invoke the Run dialog.
  • In the Run dialog box, type control and hit Enter to open Control Panel.
  • In Control Panel, locate and double-click Mail.
  • Click Show Profiles.
  • Select your Outlook profile.
  • Click Properties.
  • Click E-mail Accounts.
  • Select your email account.
  • Click Change.
  • In the Change Account dialog box, click More Settings.
  • In the Microsoft Exchange dialog box, select the Security tab.
  • On the Logon network security list, select Anonymous Authentication.
  • Click OK.
  • Click Next.
  • Click Finish.
  • Click Close on the Account Settings dialog box.
  • Click Close on the Mail Setup dialog box.
  • Click OK to close the Mail control panel.

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