Authentic help 101!

Taeloli Masani 0 Reputation points
2026-08-14T17:12:14.5766667+00:00

I am trying to add an Outlook work email. It opens my Authenticator app and gives me a number to enter on my Authenticator. Makes no sense? There’s no where to enter the number because the app is already open giving me a number!

Outlook | Outlook for mobile | Outlook for iOS | For business
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  1. AI answer

    2026-08-14T17:12:31.7966667+00:00

    This is usually a same-device number matching prompt. On iOS, when Outlook opens Authenticator and shows a number, the approval request may already be waiting inside Authenticator rather than showing a separate entry screen.

    Try this:

    1. In Outlook, start the sign-in again until the number appears.
    2. When Authenticator opens, look for a New sign-in request notification or pending approval inside the app.
    3. Tap the request, then tap or enter the matching number and select Approve.
    4. If nothing appears, manually refresh Authenticator by pulling down on the app screen.
    5. If it still does not appear, restart the phone and try the sign-in again.
    6. Make sure the phone has a working Wi-Fi or cellular connection.

    Important details:

    • For work or school accounts, Authenticator may need to be unlocked before the sign-in can be confirmed.
    • On browsers, users need to tap the notification to enter the number and approve. In Microsoft mobile apps, the number match request appears on the sign-in screen and can be completed there.
    • If the account is blocked by organization policies or registration restrictions, Authenticator setup can fail and the work or school administrator must enable the feature or adjust Conditional Access settings.
    • If the organization uses Intune app protection policies, Outlook for iOS may also require device registration before sign-in completes.

    If the prompt never appears in Authenticator after refresh and restart, the next step is to contact the work or school administrator to reset or review the authentication method.

    AI-generated content may be incorrect. Read our transparency notes for more information.

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  2. Chris-D 1,090 Reputation points Independent Advisor
    2026-08-14T17:35:08.63+00:00

    Hi Taeloli,

    Thank you for sharing the details of what happened. 

    This behavior is related to Microsoft Authenticator’s number matching sign-in security. When signing in, Microsoft may show a number that must be confirmed in the Authenticator prompt. On iOS, when Outlook and Authenticator are both on the same device, the experience may look slightly different than signing in from a computer. 

    Here are some steps you can try: 

    1. Make sure both Microsoft Outlook and Microsoft Authenticator are updated from the App Store. 
    2. Fully close both apps on your iPhone by swiping up from the bottom of the screen and swiping away the Outlook and Microsoft Authenticator app cards.  
    3. Then reopen Outlook and try adding your work account again. 
    4. When Authenticator opens, look for a prompt that says Yes, Approve, Enter number, or Show me the number again. 
    5. If you see Show me the number again, tap it to display the number again, then continue the approval. 
    6. If the prompt disappears, return to Outlook and check for any Authenticator notification banner or prompt. 
    7. If possible, try signing in from a computer or browser first. The number should appear on the computer screen, and you can then approve or enter the number in Authenticator on your iPhone. 

    For your references: How number matching works in MFA push notifications for Authenticator - Microsoft Entra ID | Microsoft Learn 

    If the issue continues or you are stuck in a sign-in loop, please reach out to your organization’s IT administrator for assistance. They may need to reset your MFA registration or require you to re-register Microsoft Authenticator for your work account. 

    You may also want to share the following Microsoft article with them: Manage authentication methods for Microsoft Entra multifactor authentication - Microsoft Entra ID | … 

    If you are unsure who your IT administrator is, you can refer to this official Microsoft guide for assistance: How do I find my Microsoft 365 admin? - Microsoft Support    

    User's image

    Once your IT administrator resets your MFA registration, you should be able to sign in again and go through the Microsoft Authenticator setup process from the beginning, including scanning a new QR code on your device. 

    I hope this information is helpful. Should you have any further questions or need additional assistance, please feel free to share them in the comment below. I'm very happy to help.  

    If the answer is helpful, please click "Yes" and kindly upvote it.

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