Solved: Outlook keeps asking for password over and over again (Office 365)

Many readers have sent me this issue recently. But now I’ve found the permanent fix. Here’s the issue many people are having: Outlook was working fine for months or years and then suddenly it begins to ask for a password. The user will enter their password and submit it and then Outlook will just ask for the password again!

It’s a very frustrating issue and some readers have spent weeks trying to fix it, sometimes spending hours on the phone with tech support.

The problem is related to how Outlook authenticates with Microsoft’s Exchange Online servers. To fix the issue we’re going to remove the old password from your computer, remove the old license activation, and then modify Outlook so that it authenticates a different way. Then we’ll be able to log in.

This entire process will take about half an hour to an hour depending on how tech savvy and familiar with the registry you are.

Step 1: Close Outlook and all Office applications

In order to make the changes we must ensure that Outlook and al Office apps (that includes Word, Excel, etc…) are closed.

Step 2: Remove the old broken credentials from Windows

  1. Open the Credential Manager from the Control Panel: https://support.microsoft.com/en-ca/help/4026814/windows-accessing-credential-manager
  2. Click on Windows Credentials
  3. Remove all Credentials that include the following: Office, Outlook, ADAL, and MSTeams
  4. Close the Credential Manager

Step 3: Remove all old Office licenses/activations

Important: If you installed Office using a product key you must make sure that you have the product key saved somewhere because we’ll need to re-enter it. If you’ve purchased Office as a subscription and pay monthly/yearly then you don’t need a product key and just will need to enter your username and password in the last step.

Note: This step is not always necessary but to make sure that we solve the problem in one go please do it anyway.

  1. Run the Command Prompt as an Administrator (search for Command Prompt and then right-click on it and select “Run as Administrator”)
  2. If you’ve installed the 64-bit version of Office then type in: cd C:\Program Files\Microsoft Office\Office16
  3. If you’ve installed the 32-bit version of Office (most people) then type in: cd C:\Program Files (x86)\Microsoft Office\Office16
  4. Display the current Office license by typing in: cscript ospp.vbs /dstatus
  5. Note the five characters of the product key or keys that are displayed
  6. Now type in cscript ospp.vbs /unpkey:<last five characters of product key>
  7. Now check if more keys still exist by re-running cscript ospp.vbs /dstatus
  8. If there are more keys then delete these too. Re-run these commands as many times as you need to until no more keys are displayed when you run cscript ospp.vbs /dstatus

Step 4: Disable Modern Authentication for Outlook

Warning: For 99% of people disabling Modern Authentication will not cause any problems. If you have Multifactor Authentication enabled on your Office 365 account then you’ll need to generate an app password to log in. But if you just log in normally then disabling modern authentication won’t change anything.

  1. Open the registry editor by searching for regedit
  2. Backup the registry: https://support.microsoft.com/en-ca/help/322756/how-to-back-up-and-restore-the-registry-in-windows
  3. In the registry navigate to HKCU\SOFTWARE\Microsoft\Office\16.0\Common\Identity by expanding the various parent keys until you reach Identity
  4. Create a new DWORD 32-bit value and call it EnableAdal
  5. Give it a value of 0
  6. Next create a new DWORD 32-bit value and call it DisableAADWAM
  7. Give it a value of 1
  8. Next create a new DWORD 32-bit value and call it DisableADALatopWAMOverride
  9. Give it a value of 1
  10. Close the registry

Step 5: Restart the computer

In order for our changes to be implemented we must restarted the computer before opening any office apps

Step 6: Open Outlook

Now open Outlook. You’ll be prompted for your password. Make sure that you select “Remember my Credentials”.

You’ll also want to re-activate Office: https://support.office.com/en-us/article/activate-office-5bd38f38-db92-448b-a982-ad170b1e187e

And that’s it! Outlook should accept your credentials and that password prompt should no longer bother you.

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