Outlook sign in and authentication app never ending loop

The two-digit number must be entered in the pending Microsoft Authenticator approval request, not in a permanent field on the app’s main screen.

Complete the pending request

1. Leave the Outlook sign-in page displaying the two-digit number.
2. Open Microsoft Authenticator and tap the sign-in notification or pending approval request.
3. Enter the two-digit number shown by Outlook, then select Approve.
   • If Outlook and Authenticator are on the same phone, the request may show only Approve/Deny instead of a number-entry box.
   • Do not use the rotating six-digit code unless the sign-in page specifically asks for a verification code.

Microsoft documents both number-entry and same-device Approve/Deny behavior.^1^

If no approval request appears

1. Update Microsoft Authenticator from the phone’s app store. Older versions that do not support number matching cannot complete this authentication.
2. In Authenticator, open Settings → Notification Settings and enable Show notifications.
3. In the phone’s system settings, allow notifications for Authenticator and disable Do Not Disturb/Quiet mode temporarily.
4. Ensure Date & time is set automatically.
5. Switch between Wi-Fi and mobile data, and temporarily disconnect any VPN.
6. Return to Outlook and initiate a new sign-in request, then immediately check Authenticator.

These are Microsoft’s recommended checks when Authenticator notifications do not arrive.^2^

Use another registered verification method

On the Microsoft sign-in page, select Sign in another way, Use a different verification method, or I can’t use my Microsoft Authenticator app right now. Choose an already configured method such as SMS, phone call, security key, or another authenticator.

If another method works, update the account’s Security info and re-register Authenticator. Do not remove the existing Authenticator registration until another working verification method is available, or the account could become inaccessible.

If this is a work or school account

If no alternative method is offered, the organization’s IT administrator must reset the registration. Ask for:

“Require me to re-register for multifactor authentication because the Authenticator number-matching prompt does not appear.”

An Authentication Administrator can do this in:

1. Microsoft Entra admin center
2. Entra ID → Users
3. Select the affected user.
4. Select Authentication methods.
5. Select Require re-register MFA.

This removes the user’s registered phone numbers, Authenticator registrations, and software OATH tokens; the user is then prompted to configure MFA again at the next sign-in.^3^

If this is a personal Microsoft account

After completing the notification checks, open Authenticator’s top-level menu and select Send feedback to capture diagnostic logs, then contact Microsoft Support or use the Microsoft Authenticator forum.^2^

References

1. How number matching works in MFA push notifications for Authenticator - Authentication methods policy
2. [Personal accounts](https://support.microsoft.com/authenticator/troubleshoot-problems-with-microsoft-authenticator)
3. Manage user authentication methods for Microsoft Entra multifactor authentication