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I've just installed Outlook 2013 and have all the clients connecting to it, however, whenever a client connects via outlook they are prompted with an invalid SSL message for myserver.mydomain.local. I have a wildcard certificate setup and assigned in IIS for *.example.com so I understand why the message appears but I am not exactly sure what to do about it and where to start looking without poking random things.

From the research I've done, I can see that this can be caused by the autodiscover service so I have changed the domain DNS records to not use an A record but instead use an SRV record inline with this Microsoft article. Should this be sorting the issue and I am just being impatient with propagation or am I barking up the wrong tree?

This post fixed the issue with an SRV record: Exchange 2013 SSL Warning in Outlook

Edit Interestingly running get-ClientAccessServer | ft identity,AutodiscoverServiceInternalUri shows my internal FQDN and not my external one which I assume is the issue. I am going to try changing this now.

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Make sure the URL fit the certificate.

Issue those command via powershell to validate;

Get-ActiveSyncVirtualDirectory | fl internalurl,externalurl
Get-AutoDiscoverVirtualDirectory | fl internalurl,externalurl
Get-ECPVirtualDirectory | fl internalurl,externalurl
Get-OabVirtualDirectory | fl internalurl,externalurl
Get-WebServicesVirtualDirectory | fl internalurl,externalurl

Change them to make them match the certificate;

Get-ActiveSyncVirtualDirectory -server EXCHANGE | Set-ActiveSyncVirtualDirectory -ExternalUrl 'https://mail.example.com/Microsoft-Server-ActiveSync' -InternalUrl 'https://mail.example.com/Microsoft-Server-ActiveSync'
Get-AutodiscoverVirtualDirectory -server EXCHANGE | Set-AutodiscoverVirtualDirectory -ExternalUrl 'https://mail.example.com/Autodiscover/Autodiscover.xml' -InternalUrl 'https://mail.example.com/Autodiscover/Autodiscover.xml'
Get-ECPVirtualDirectory -server EXCHANGE | Set-ECPVirtualDirectory -ExternalUrl 'https://mail.example.com/ECP' -InternalUrl 'https://mail.example.com/ECP'
Get-OabVirtualDirectory -server EXCHANGE | Set-OabVirtualDirectory -ExternalUrl 'https://mail.example.com/OAB' -InternalUrl 'https://mail.example.com/OAB'
Get-WebServicesVirtualDirectory -server EXCHANGE | Set-WebServicesVirtualDirectory -ExternalUrl 'https://mail.example.com/EWS/Exchange.asmx' -InternalUrl 'https://mail.example.com/EWS/Exchange.asmx'

A example using the GUI there

  • I'll take a look at this now, many thanks. I'll report back. – webnoob Jan 9 '15 at 14:13
  • Two things: 1 - The autodiscover one has nothing set in it already, why would this be? 2 - Just to confirm, I'm even changing the internal ones to do an external lookup? – webnoob Jan 9 '15 at 14:15
  • I would do a split DNS setup, so internaly the mail.example.com will resolve to the internal IP, while user on the road will still get the public IP – yagmoth555 Jan 9 '15 at 14:17
  • Set it with the powershell listed above (for internalurl and external), as it will modify the IIS correctly. Do a iisreset too after – yagmoth555 Jan 9 '15 at 14:24
  • Ok, I've done as stated above and restarted IIS but I still get the SSL warning on outlook startup. Any ideas? – webnoob Jan 9 '15 at 14:34

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