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Outlook Autodiscover is using internal URL instead of external causing cert error, how do make it use external URL?

Anonymous
2025-05-29T14:21:17+00:00

Stand-Alone Exchange Server 2016 with Outlook 2016 client:

The Outlook profile wizard completes without error but, every time Outlook is opened, a Security Alert opens. It shows the internal URL for the Exchange server at the top and states "The name on the security certificate is invalid or does not match...". This makes sense because the certificate only contains external URLs. I click "Yes" and the mailbox appears to work properly.

How do I force Exchange/Outlook to use the Exchange server's external URL when creating user profiles so I don't get the Security Alert?

Thank you in advance!

Outlook | Windows | Classic Outlook for Windows | For business

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Anonymous
2025-05-31T19:33:05+00:00

Hello,

Thank you for interacting with us by posting your issue on this forum.

To fix this issue we can try these troubleshooting steps:

  1. Update Autodiscover Settings: Change the Service Connection Point (SCP) in Active Directory to point to the external URL.
  2. Set External URLs in Exchange: Ensure services like OWA and EWS use the external URL (Set-WebServicesVirtualDirectory).
  3. Modify Outlook Anywhere Settings: Use (Set-OutlookAnywhere) to make Outlook connect through the external URL.
  4. Check DNS Records: Verify Autodiscover DNS entries direct Outlook to the external address.

Hope this help! Have a nice day!

Regards,

Zenitsu | Microsoft Community Moderator

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  1. Anonymous
    2025-06-09T20:28:54+00:00

    This was very close to the solution so I will give you credit.

    I posted the exact solution as a separate comment in this post for others to reference.

    Thank you!

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  2. Anonymous
    2025-06-09T20:26:36+00:00

    SOLUTION:

    Open EMS as Administrator

    (Run the command below after replacing 'server' with your Exchange server's NetBIOS name and replacing "domain.com" with your public domain name.)

    Set-ClientAccessServer -Identity 'server' -AutoDiscoverServiceInternalUri 'https://autodiscover.domain.com/Autodiscover/Autodiscover.xml'

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  3. Anonymous
    2025-06-07T21:09:52+00:00

    Hello, We noticed that we haven't received a response to our last message. We would like to check if the issue you raised is still ongoing. If it is, please reply to this thread so we can continue assisting you.Regards,Zenitsu | Microsoft Community Moderator

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