email not synchronizing or receiving or sending email

Bridget Skvarla 0 Reputation points
2026-11-09T22:41:49.42+00:00

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I have 3 different email that I work on. The [Moderator note: Personally Identifiable Information removed]@hilbornehawkin.com is not working

Outlook | Windows | Classic Outlook for Windows | For business
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  1. Ivory 2,710 Reputation points Independent Advisor
    2026-11-09T23:54:56.7266667+00:00

    Hi Bridget,

    That banner indicates that Outlook is unable to verify the sign-in session for your account requires the account to be re-authenticated.

    To help narrow down the cause, could you please let me know:

    1. What happens when you click "Sign in via browser"?
    2. Does the sign-in complete successfully?
      • Do you receive an error message or repeated password prompts?
      Are you able to sign in to the account directly through a web browser (for example, Outlook on the web)? Is the issue occurring on only one device, or do you see the same sign-in prompt on other devices or when accessing Outlook on the web?

    In the meantime, please try the following steps:

    1/ Re-sign in to Office

    1. Open any Office app and go to File > Office Account.
    2. Sign out of the affected account.
    3. Close all Office applications completely.
    4. Reopen Outlook and sign in again.

    This will refresh the Office authentication token that Outlook uses.

    2/ Clear saved Office credentials

    1. Sign out of all Office applications and close them.
    2. Open Credential Manager in Windows.
    3. Under Windows Credentials and Generic Credentials, remove entries related to:
      • Microsoft 365
        • Office
          • The affected work account
          1. Restart the computer.
          2. Open Outlook or another Office application and sign in again.

    Please remove only credentials that are clearly associated with Microsoft Office or the affected work account

    3/ Create a new Outlook profile

    A corrupted Outlook profile can sometimes cause authentication issues.

    1. Close Outlook.
    2. Open Control Panel > Mail > Show Profiles.
    3. Select Add to create a new profile.
    4. Add and sign in to the work account.
    5. Set the new profile as the default and test Outlook.

    For more information, please consult Create a profile in classic Outlook for Windows | Microsoft Support

    To help with further troubleshooting, please share the results of the above steps. Additional details will help determine whether the issue is related to Outlook, stored credentials, or the account's authentication settings.

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  2. AI answer

    2026-11-09T22:42:32.92+00:00

    Click Sign in via browser in the yellow Outlook banner and complete sign-in for the affected @hilbornehawkin.com account; the banner indicates that this account requires authentication before Outlook can synchronize it.

    Reauthenticate the affected account

    1. In classic Outlook, click Sign in via browser.
    2. In the browser window, verify that the displayed address is the affected @hilbornehawkin.com mailbox—not either of your other accounts.
    3. Enter the mailbox password and complete any multifactor authentication request.
    4. Return to Outlook and select Send/Receive → Send/Receive All Folders.
    5. Confirm that the yellow banner disappears and test both:
      • Receiving a message from another address.
      • Sending a message to another address.

    If the password was recently changed or expired, use the current mailbox password. Outlook authentication problems can occur when the password stored by Outlook no longer matches the email provider’s password.^1^

    If browser sign-in fails

    Try signing in directly through the organization’s normal webmail page.

    • If webmail also cannot send or receive: this is not limited to the Outlook desktop profile. Ask the organization’s Microsoft 365 or email administrator to check that the mailbox is active, licensed, and permitted to sign in. Provide the exact browser error.
    • If webmail works: the mailbox service is operating, so continue with the Outlook-specific steps below.

    Do not remove the account until web sign-in works and any locally stored mail is known to be backed up or retained on the server.

    If webmail works but classic Outlook still does not sync

    1. Check Outlook’s status bar. If it says Working Offline, select Send/Receive → Work Offline once to reconnect.
    2. If it says Disconnected or Trying to connect, close and reopen Outlook after completing browser authentication.
    3. Repair only the affected account:
      • File → Account Settings → Account Settings
      • Select the affected mailbox on the Email tab.
      • Select Repair, follow the wizard, and restart Outlook.^2^
    4. If Repair is unavailable or does not resolve it, open the Windows Get Help app, search for Outlook password problem, and run the classic Outlook authentication check troubleshooter. The troubleshooter applies to classic Outlook on Windows, not new Outlook.^3^

    If it remains unresolved, record the exact error from Send/Receive → Show Progress → Errors and provide it to the organization’s email administrator.

    References

    1. Troubleshoot Outlook email setup | Microsoft Support
    2. Fix your Outlook email connection by repairing your profile | Microsoft Support
    3. Classic Outlook troubleshooters | Microsoft Support
    AI-generated content may be incorrect. Read our transparency notes for more information.

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