email not synchronizing or receiving or sending email

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