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gsswho6Flag for United States of America

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Outlook Security Certificate

Hello All,

I have a customer who has SBS2011 and he use to use the exchange... Last year we stopped using the exchange on SBS and moved him over to Office 365... We are not using Azure/etc just moved over his domain to office 365 and repointed all of his outlook clients to office 365... Worked like a charm.

However sometimes the users get a Security Alert when opening/closing outlook .... The Security certificate has expired or is not yet valid. Any idea why they are recieving this? I assume it has to do with the old SMS Exchange? Why would his outlook be throwing that error if its pointed to office 365 an not his old on premise exchange?

If anyone has any ideas please shoot them my way... Thanks
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Wayne88
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Can you open up the security alert and see which security certificate has expired?

Outlook will try to use a few different ways in trying to obtain the Autodiscover information and you can exclude some of the methods as explained here: https://support.microsoft.com/en-us/help/2212902/unexpected-autodiscover-behavior-when-you-have-registry-settings-under-the-autodiscover-key
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Adam Brown
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Hello Mate,

I agree with Adam, you SBS server object is still exist in AD hence outlook client try to connect using Autodiscover SCP object. To fix the issue you  have following options

1) Redirect the SCP request to O365 using powershell command

get-clientaccessserver | set-clientaccessserver -autodiscoverserviceinternaluri "https://autodiscover.outlook.com/autodiscover/autodiscover.xml"

2) Since all mailboxes are completely migrated to cloud you can remove the server object from ADSI edit or uninstall the Exchange server

To remove the server open ADSI-Edit and go to configuration

Navigate to this path:

CN=Configuration,DC=DOMAIN,DC=LOCAL
CN=Services
CN=Microsoft Exchange
CN=EXCHANGE_ORG
CN=Administrative Group
CN=Servers

Delete the Server object

3) Disable the SCP at outlook client by doing registry changes

HKEY_CURRENT_USER\Software\Policies\Microsoft\Office\x.0\Outlook\AutoDiscover

ExcludeScpLookup set value to 0

Restart the client machine

https://support.microsoft.com/en-in/help/2212902/unexpected-autodiscover-behavior-when-you-have-registry-settings-under-the-autodiscover-key

You can apply to all clients using GPO

https://support.microsoft.com/en-in/help/2612922/how-to-control-outlook-autodiscover-by-using-group-policy

Regards,
Kumar
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Thanks this did the job.