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Certificate errors in Exchange 2010

Posted on 2014-07-18
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Last Modified: 2014-08-06
We are using Exchange Server 2010 on Server 2008 R2. Recently upgraded some clients from Outlook 2003 to Outlook 2013.

Now they are getting certificate errors. It looks like Outlook is using the internal hostname of our Exchange server to connect. Our certificate only has the external hostname listed on it, and that's what I want Outlook to use to connect to the server both internally and externally.

If I go into "Connection Status" on Outlook, it shows the internal hostname in the "Server Name" field.

What are the EMS commands to check / set the various hostnames for Exchange Server so I can set them to all be the external hostname?
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Question by:Frosty555
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by:Seth Simmons
ID: 40204988
this article should help with the commands

Managing Exchange 2010 External/Internal URL's via PowerShell
http://social.technet.microsoft.com/wiki/contents/articles/5163.managing-exchange-2010-externalinternal-url-s-via-powershell.aspx
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by:Adam Farage
ID: 40204997
So I am taking it you are connecting over RPC / HTTPS (Outlook Anywhere)?

If that is the case, just create a forward lookup zone (if not already in existence) for domain.com (this should exist if you are doing split DNS) and then point an A record for mail.company.com to the VIP (or IP) of the CAS (or CAS Array).

From there you can set the ExternalURL:

Get-OutlookAnywhere | Set-OutlookAnywhere -ExternalHostname https://mail.domain.com/

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by:Frosty555
ID: 40205050
Internally, I think that Outlook is using just regular Exchange RPC for Exchange connectivity (not HTTP). Connecting over HTTP only happens on "slow networks".

The URLs that the commands that Seth linked to all look correct, they're the external hostnames. Adam - I have set the OutlookAnywhere hostname, too, and it seems to be correct.

Still, though, it tries to connect using the internal hostname of the server.

I'm happy to configure it to always use RPC over HTTP (e.g. similar to how Exchange 2013 works), but where do I configure that so that it is automatically configured that way via Autodiscover?
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Adam Farage earned 500 total points
ID: 40205085
I think this might be an AutoDiscover issue. Here is a detailed post I wrote yesterday: http://www.experts-exchange.com/Software/Server_Software/Email_Servers/Exchange/Q_28478577.html

Basically clients internally will look at the SCP for AutoDiscover to find out where they should pull the AutoDiscover.xml. this is new for you, since Outlook 2003 does not have AutoDiscover at all.

I would first start and read this through, and then look at the SCP. Make sure the location the SCP is pointing to is listed on the certificate, and if not make sure autodiscover.company.com is listed on the SSL certificate (that is assigned to the IIS service) and then change the SCP to autodiscover.company.com/autodiscover/autodiscover.xml. If the FQDN autodiscover.company.com is listed, these errors should go away.

Its not an InternalURL or ExternalURL issue if this prompt is coming up either when or shortly after Outlook is started.. it would be autoD :)
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by:Frosty555
ID: 40205086
I set the "Server" property for the EXCH and EXPR OutlookProviders to be the external hostname of the server, and recycled the msExchangeAutodiscoverAppPool Application Pool in IIS.

In Outlook, when I go through the "test autodiscover configuration" the EXPR service comes back with the correct, external hostname. For some reason the EXCH service still comes back with the internal hostname. Not sure why.

--edit--

Checked the SCP record, it is pointing at the external hostname. I think I ran into the SCP record issue at some point in the past (we did have a handful of "questionably licensed" Outlook 2007 clients that we have finally managed to get rid of).
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by:-MAS
ID: 40205763
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